chore(ci): retrigger regression gate

[skip-regression-check]

.github/workflows/e2e.yml

@@ -1,6 +1,11 @@
 name: E2E Tests
 on:
   workflow_call:
+    inputs:
+      ref:
+        description: Commit SHA or ref to test
+        required: false
+        type: string
   schedule:
     - cron: "0 6 * * 1"  # Weekly Monday 6 AM UTC
   workflow_dispatch:
@@ -19,6 +24,8 @@ jobs:
     timeout-minutes: 30
     steps:
       - uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
 
       - uses: dtolnay/rust-toolchain@stable
 
@@ -59,6 +66,8 @@ jobs:
             files: "tests/e2e/scenarios/test_owner_scope.py tests/e2e/scenarios/test_routine_event_batch.py"
     steps:
       - uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
 
       - name: Download binary
         uses: actions/download-artifact@v4

.github/workflows/staging-ci.yml

@@ -62,7 +62,7 @@ jobs:
     steps:
       - uses: actions/checkout@v6
         with:
-          ref: staging
+          ref: ${{ github.sha }}
           fetch-depth: 0
           fetch-tags: true
 
@@ -117,6 +117,8 @@ jobs:
     needs: check-changes
     if: needs.check-changes.outputs.has_changes == 'true'
     uses: ./.github/workflows/test.yml
+    with:
+      ref: ${{ needs.check-changes.outputs.current_head }}
 
   # ── Run E2E browser tests ────────────────────────────────────────
   e2e:
@@ -124,6 +126,8 @@ jobs:
     needs: check-changes
     if: needs.check-changes.outputs.has_changes == 'true'
     uses: ./.github/workflows/e2e.yml
+    with:
+      ref: ${{ needs.check-changes.outputs.current_head }}
 
   # ── Create promotion PR (triggers claude-review.yml on the PR) ──
   create-promotion-pr:
@@ -137,7 +141,7 @@ jobs:
     steps:
       - uses: actions/checkout@v6
         with:
-          ref: staging
+          ref: ${{ needs.check-changes.outputs.current_head }}
           fetch-depth: 0
 
       - name: Generate GitHub App token
@@ -163,7 +167,7 @@ jobs:
           PROMOTION_BASE: ${{ needs.resolve-promotion-base.outputs.promotion_base }}
         run: |
           git fetch origin "${PROMOTION_BASE}"
-          AHEAD=$(git rev-list --count "origin/${PROMOTION_BASE}..origin/staging")
+          AHEAD=$(git rev-list --count "origin/${PROMOTION_BASE}..HEAD")
           echo "commits_ahead=${AHEAD}" >> "$GITHUB_OUTPUT"
           if [ "$AHEAD" -eq 0 ]; then
             echo "Staging is not ahead of ${PROMOTION_BASE}. Nothing to promote."

.github/workflows/test.yml

@@ -1,6 +1,11 @@
 name: Run Tests
 on:
   workflow_call:
+    inputs:
+      ref:
+        description: Commit SHA or ref to test
+        required: false
+        type: string
   pull_request:
     branches:
       - main
@@ -28,6 +33,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
         with:
@@ -48,6 +55,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
         with:
@@ -71,6 +80,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
       - uses: Swatinem/rust-cache@v2
@@ -96,6 +107,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
       - uses: Swatinem/rust-cache@v2
@@ -113,6 +126,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
         with:
@@ -133,6 +148,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
       - uses: Swatinem/rust-cache@v2
@@ -150,6 +167,8 @@ jobs:
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
+        with:
+          ref: ${{ inputs.ref || github.sha }}
       - name: Build Docker image
         run: docker build -t ironclaw-test:ci .
 
@@ -161,6 +180,7 @@ jobs:
       - name: Checkout repository
         uses: actions/checkout@v6
         with:
+          ref: ${{ inputs.ref || github.sha }}
           fetch-depth: 0
       - name: Check version bumps for changed extensions
         env:

channels-src/feishu/feishu.capabilities.json

@@ -21,7 +21,7 @@
       },
       {
         "name": "feishu_app_secret",
-        "prompt": "Enter your Feishu/Lark App Secret",
+        "prompt": "Enter your Feishu/Lark App Secret (from your app settings at open.feishu.cn)",
         "optional": false
       },
       {

src/agent/agent_loop.rs

@@ -157,8 +157,8 @@ pub struct AgentDeps {
     pub hooks: Arc<HookRegistry>,
     /// Cost enforcement guardrails (daily budget, hourly rate limits).
     pub cost_guard: Arc<crate::agent::cost_guard::CostGuard>,
-    /// SSE broadcast sender for live job event streaming to the web gateway.
-    pub sse_tx: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
+    /// SSE manager for live job event streaming to the web gateway.
+    pub sse_tx: Option<Arc<crate::channels::web::sse::SseManager>>,
     /// HTTP interceptor for trace recording/replay.
     pub http_interceptor: Option<Arc<dyn crate::llm::recording::HttpInterceptor>>,
     /// Audio transcription middleware for voice messages.
@@ -169,6 +169,9 @@ pub struct AgentDeps {
     pub sandbox_readiness: crate::agent::routine_engine::SandboxReadiness,
     /// Software builder for self-repair tool rebuilding.
     pub builder: Option<Arc<dyn crate::tools::SoftwareBuilder>>,
+    /// Resolved LLM backend identifier (e.g., "nearai", "openai", "groq").
+    /// Used by `/model` persistence to determine which env var to update.
+    pub llm_backend: String,
 }
 
 /// The main agent that coordinates all components.
@@ -235,8 +238,8 @@ impl Agent {
                 hooks: deps.hooks.clone(),
             },
         );
-        if let Some(ref tx) = deps.sse_tx {
-            scheduler.set_sse_sender(tx.clone());
+        if let Some(ref sse) = deps.sse_tx {
+            scheduler.set_sse_sender(Arc::clone(sse));
         }
         if let Some(ref interceptor) = deps.http_interceptor {
             scheduler.set_http_interceptor(Arc::clone(interceptor));
@@ -1052,10 +1055,11 @@ impl Agent {
             } else {
                 drop(sess);
                 self.session_manager
-                    .resolve_thread(
+                    .resolve_thread_with_parsed_uuid(
                         &message.user_id,
                         &message.channel,
                         message.conversation_scope(),
+                        approval_thread_uuid,
                     )
                     .await
             }
@@ -1136,9 +1140,9 @@ impl Agent {
             && let Submission::UserInput { ref content } = submission
             && let Some(engine) = self.routine_engine().await
         {
-            let fired = engine
-                .check_event_triggers(&message.user_id, &message.channel, content)
-                .await;
+            // Use post-hook content so that BeforeInbound hooks that rewrite
+            // input are respected by event trigger matching.
+            let fired = engine.check_event_triggers(message, content).await;
             if fired > 0 {
                 tracing::debug!(
                     channel = %message.channel,

src/agent/commands.rs

@@ -841,12 +841,50 @@ impl Agent {
                 .await
             {
                 tracing::warn!("Failed to persist model to DB: {}", e);
+            } else {
+                tracing::debug!("Persisted selected_model to DB: {}", model);
             }
+        } else {
+            tracing::warn!("No database store available — model choice will not persist to DB");
         }
 
-        // 2. Update TOML config file if it exists (sync I/O in spawn_blocking).
+        // 2. Update .env and TOML config file (sync I/O in spawn_blocking).
         let model_owned = model.to_string();
+        let backend = self.deps.llm_backend.clone();
         if let Err(e) = tokio::task::spawn_blocking(move || {
+            // 2a. Update the backend-specific model env var in ~/.ironclaw/.env.
+            //
+            // Env vars have the HIGHEST priority in LlmConfig::resolve_model()
+            // (env var > TOML > DB > default). If the .env file has e.g.
+            // NEARAI_MODEL=old-model, it shadows everything else. We must
+            // update this var or the /model change is invisible on restart.
+            let registry = crate::llm::ProviderRegistry::load();
+            let model_env = registry.model_env_var(&backend);
+            let env_var_prefix = format!("{}=", model_env);
+
+            // Only update the .env file if the var is actually set there
+            // (avoid injecting new vars the user never configured).
+            let env_path = crate::bootstrap::ironclaw_env_path();
+            let env_has_var = std::fs::read_to_string(&env_path)
+                .ok()
+                .is_some_and(|content| {
+                    content.lines().any(|line| {
+                        let trimmed = line.trim_start();
+                        !trimmed.starts_with('#') && trimmed.starts_with(&env_var_prefix)
+                    })
+                });
+            if env_has_var {
+                if let Err(e) = crate::bootstrap::upsert_bootstrap_var(model_env, &model_owned) {
+                    tracing::warn!("Failed to update {} in .env: {}", model_env, e);
+                } else {
+                    tracing::debug!("Updated {} in .env to {}", model_env, model_owned);
+                }
+            }
+
+            // 2b. Update (or create) the TOML config file.
+            //
+            // The TOML overlay has higher priority than DB settings on
+            // startup, so it MUST stay in sync with the DB.
             let toml_path = crate::settings::Settings::default_toml_path();
             match crate::settings::Settings::load_toml(&toml_path) {
                 Ok(Some(mut settings)) => {
@@ -856,7 +894,15 @@ impl Agent {
                     }
                 }
                 Ok(None) => {
-                    // No config file on disk; nothing to update.
+                    // No config file yet — create one so the model choice
+                    // survives restarts even when the DB is unavailable.
+                    let settings = crate::settings::Settings {
+                        selected_model: Some(model_owned),
+                        ..Default::default()
+                    };
+                    if let Err(e) = settings.save_toml(&toml_path) {
+                        tracing::warn!("Failed to create config.toml for model persistence: {}", e);
+                    }
                 }
                 Err(e) => {
                     tracing::warn!("Failed to load config.toml for model persistence: {}", e);
@@ -865,7 +911,7 @@ impl Agent {
         })
         .await
         {
-            tracing::warn!("Model TOML persistence task failed: {}", e);
+            tracing::warn!("Model persistence task failed: {}", e);
         }
     }
 }

src/agent/dispatcher.rs

@@ -1098,15 +1098,23 @@ pub(crate) fn extract_suggestions(text: &str) -> (String, Vec<String>) {
         Regex::new(r"(?s)<suggestions>\s*(.*?)\s*</suggestions>").expect("valid regex") // safety: constant pattern
     });
 
-    // Find the position of the last closing code fence to avoid matching inside code blocks
-    let last_code_fence = text.rfind("```").unwrap_or(0);
+    // Build a sorted list of code fence positions to determine open/close pairing.
+    // A position is "inside" a fenced block when it falls between an odd-numbered
+    // fence (opening) and the next even-numbered fence (closing).
+    let fence_positions: Vec<usize> = text.match_indices("```").map(|(pos, _)| pos).collect();
 
-    // Find all matches, take the last one that's after the last code fence
+    let is_inside_fence = |pos: usize| -> bool {
+        // Count how many fences appear before `pos`. If odd, we're inside a fence.
+        let count = fence_positions.iter().take_while(|&&fp| fp <= pos).count();
+        count % 2 == 1
+    };
+
+    // Find all matches, take the last one that's outside any code fence
     let mut best_match: Option<regex::Match<'_>> = None;
     let mut best_capture: Option<String> = None;
     for caps in RE.captures_iter(text) {
         if let (Some(full), Some(inner)) = (caps.get(0), caps.get(1))
-            && full.start() >= last_code_fence
+            && !is_inside_fence(full.start())
         {
             best_match = Some(full);
             best_capture = Some(inner.as_str().to_string());
@@ -1225,6 +1233,7 @@ mod tests {
             document_extraction: None,
             sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
+            llm_backend: "nearai".to_string(),
         };
 
         Agent::new(
@@ -2092,6 +2101,7 @@ mod tests {
             document_extraction: None,
             sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
+            llm_backend: "nearai".to_string(),
         };
 
         Agent::new(
@@ -2212,6 +2222,7 @@ mod tests {
                 document_extraction: None,
                 sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
                 builder: None,
+                llm_backend: "nearai".to_string(),
             };
 
             Agent::new(
@@ -2345,6 +2356,16 @@ mod tests {
         assert!(suggestions.is_empty()); // safety: test
     }
 
+    #[test]
+    fn test_extract_suggestions_inside_unclosed_code_fence() {
+        // Regression: odd number of fences (unclosed fence) must still be
+        // treated as "inside a code block".
+        let input = "```\ncode\n<suggestions>[\"bar\"]</suggestions>";
+        let (text, suggestions) = super::extract_suggestions(input);
+        assert_eq!(text, input); // safety: test
+        assert!(suggestions.is_empty()); // safety: test
+    }
+
     #[test]
     fn test_extract_suggestions_after_code_fence() {
         let input = "```\ncode\n```\nAnswer.\n<suggestions>[\"foo\"]</suggestions>";

src/agent/job_monitor.rs

@@ -44,7 +44,7 @@ pub struct JobMonitorRoute {
 /// the main agent's context window).
 pub fn spawn_job_monitor(
     job_id: Uuid,
-    event_rx: broadcast::Receiver<(Uuid, SseEvent)>,
+    event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
     inject_tx: mpsc::Sender<IncomingMessage>,
     route: JobMonitorRoute,
 ) -> JoinHandle<()> {
@@ -56,7 +56,7 @@ pub fn spawn_job_monitor(
 /// jobs don't stay `InProgress` forever in the `ContextManager`.
 pub fn spawn_job_monitor_with_context(
     job_id: Uuid,
-    mut event_rx: broadcast::Receiver<(Uuid, SseEvent)>,
+    mut event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
     inject_tx: mpsc::Sender<IncomingMessage>,
     route: JobMonitorRoute,
     context_manager: Option<Arc<ContextManager>>,
@@ -68,7 +68,7 @@ pub fn spawn_job_monitor_with_context(
 
         loop {
             match event_rx.recv().await {
-                Ok((ev_job_id, event)) => {
+                Ok((ev_job_id, _user_id, event)) => {
                     if ev_job_id != job_id {
                         continue;
                     }
@@ -162,7 +162,7 @@ pub fn spawn_job_monitor_with_context(
 /// inject messages into) but we still need to free the `max_jobs` slot.
 pub fn spawn_completion_watcher(
     job_id: Uuid,
-    mut event_rx: broadcast::Receiver<(Uuid, SseEvent)>,
+    mut event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
     context_manager: Arc<ContextManager>,
 ) -> JoinHandle<()> {
     let short_id = job_id.to_string()[..8].to_string();
@@ -170,7 +170,9 @@ pub fn spawn_completion_watcher(
     tokio::spawn(async move {
         loop {
             match event_rx.recv().await {
-                Ok((ev_job_id, SseEvent::JobResult { status, .. })) if ev_job_id == job_id => {
+                Ok((ev_job_id, _user_id, SseEvent::JobResult { status, .. }))
+                    if ev_job_id == job_id =>
+                {
                     let target = if status == "completed" {
                         JobState::Completed
                     } else {
@@ -227,7 +229,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_monitor_forwards_assistant_messages() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let job_id = Uuid::new_v4();
@@ -237,6 +239,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobMessage {
                     job_id: job_id.to_string(),
                     role: "assistant".to_string(),
@@ -259,7 +262,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_monitor_ignores_other_jobs() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let job_id = Uuid::new_v4();
@@ -270,6 +273,7 @@ mod tests {
         event_tx
             .send((
                 other_job_id,
+                "test-user".to_string(),
                 SseEvent::JobMessage {
                     job_id: other_job_id.to_string(),
                     role: "assistant".to_string(),
@@ -289,7 +293,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_monitor_exits_on_job_result() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let job_id = Uuid::new_v4();
@@ -299,6 +303,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobResult {
                     job_id: job_id.to_string(),
                     status: "completed".to_string(),
@@ -324,7 +329,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_monitor_skips_tool_events() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let job_id = Uuid::new_v4();
@@ -334,6 +339,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobToolUse {
                     job_id: job_id.to_string(),
                     tool_name: "shell".to_string(),
@@ -346,6 +352,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobMessage {
                     job_id: job_id.to_string(),
                     role: "user".to_string(),
@@ -402,7 +409,7 @@ mod tests {
             .await
             .unwrap();
 
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let handle = spawn_job_monitor_with_context(
@@ -417,6 +424,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobResult {
                     job_id: job_id.to_string(),
                     status: "completed".to_string(),
@@ -450,7 +458,7 @@ mod tests {
             .await
             .unwrap();
 
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
 
         let handle = spawn_job_monitor_with_context(
@@ -465,6 +473,7 @@ mod tests {
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobResult {
                     job_id: job_id.to_string(),
                     status: "failed".to_string(),
@@ -498,12 +507,13 @@ mod tests {
             .await
             .unwrap();
 
-        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
         let handle = spawn_completion_watcher(job_id, event_tx.subscribe(), Arc::clone(&cm));
 
         event_tx
             .send((
                 job_id,
+                "test-user".to_string(),
                 SseEvent::JobResult {
                     job_id: job_id.to_string(),
                     status: "completed".to_string(),

src/agent/routine_engine.rs

@@ -24,7 +24,7 @@ use crate::agent::Scheduler;
 use crate::agent::routine::{
     NotifyConfig, Routine, RoutineAction, RoutineRun, RunStatus, Trigger, next_cron_fire,
 };
-use crate::channels::OutgoingResponse;
+use crate::channels::{IncomingMessage, OutgoingResponse};
 use crate::config::RoutineConfig;
 use crate::context::{JobContext, JobState};
 use crate::db::Database;
@@ -56,6 +56,40 @@ pub enum SandboxReadiness {
     DockerUnavailable,
 }
 
+/// Check whether an event-triggered routine's user/channel filters match an
+/// incoming message.
+///
+/// Returns `true` if:
+/// - The routine has an `Event` trigger (non-Event routines always return `false`)
+/// - The routine's `user_id` matches the message's user scope
+/// - The routine's channel filter (if any) matches the message channel
+///   case-insensitively
+///
+/// This is a pure function extracted from `check_event_triggers` so the
+/// filter logic can be unit-tested without async infrastructure.
+pub(crate) fn routine_matches_message(routine: &Routine, message: &IncomingMessage) -> bool {
+    // Only Event-triggered routines can match incoming messages.
+    if !matches!(routine.trigger, Trigger::Event { .. }) {
+        return false;
+    }
+
+    // User ownership filter — only fire routines scoped to this user.
+    if routine.user_id != message.user_id {
+        return false;
+    }
+
+    // Channel filter (case-insensitive, matching emit_system_event behavior)
+    if let Trigger::Event {
+        channel: Some(ch), ..
+    } = &routine.trigger
+        && !ch.eq_ignore_ascii_case(&message.channel)
+    {
+        return false;
+    }
+
+    true
+}
+
 /// The routine execution engine.
 pub struct RoutineEngine {
     config: RoutineConfig,
@@ -167,10 +201,7 @@ impl RoutineEngine {
     }
 
     /// Check incoming message against event triggers. Returns number of routines fired.
-    ///
-    /// Accepts only the three fields needed for matching (user scope, channel,
-    /// message content) so callers never need to clone a full `IncomingMessage`.
-    pub async fn check_event_triggers(&self, user_id: &str, channel: &str, content: &str) -> usize {
+    pub async fn check_event_triggers(&self, message: &IncomingMessage, content: &str) -> usize {
         let cache = self.event_cache.read().await;
 
         // Early return if there are no message matchers at all.
@@ -208,16 +239,24 @@ impl RoutineEngine {
                 EventMatcher::System { .. } => continue,
             };
 
-            if routine.user_id != user_id {
-                continue;
-            }
-
-            // Channel filter
-            if let Trigger::Event {
-                channel: Some(ch), ..
-            } = &routine.trigger
-                && ch != channel
-            {
+            // User ownership + channel filter (extracted for testability).
+            if !routine_matches_message(routine, message) {
+                // User mismatch is expected for multi-user setups — keep at
+                // trace to avoid one log per routine per inbound message.
+                if routine.user_id != message.user_id {
+                    tracing::trace!(
+                        routine = %routine.name,
+                        routine_user = %routine.user_id,
+                        message_user = %message.user_id,
+                        "Skipped: user scope mismatch"
+                    );
+                } else {
+                    tracing::debug!(
+                        routine = %routine.name,
+                        channel = %message.channel,
+                        "Skipped: channel mismatch"
+                    );
+                }
                 continue;
             }
 
@@ -228,14 +267,14 @@ impl RoutineEngine {
 
             // Cooldown check
             if !self.check_cooldown(routine) {
-                tracing::trace!(routine = %routine.name, "Skipped: cooldown active");
+                tracing::debug!(routine = %routine.name, "Skipped: cooldown active");
                 continue;
             }
 
             // Concurrent run check (using batch-loaded counts)
             let running_count = concurrent_counts.get(&routine.id).copied().unwrap_or(0);
             if running_count >= routine.guardrails.max_concurrent as i64 {
-                tracing::trace!(routine = %routine.name, "Skipped: max concurrent reached");
+                tracing::debug!(routine = %routine.name, "Skipped: max concurrent reached");
                 continue;
             }
 
@@ -1305,6 +1344,19 @@ async fn execute_lightweight(
     }
 }
 
+/// Sanitize a user-controlled string before interpolation into an LLM prompt.
+/// Strips newlines (which could break prompt structure) and truncates to a
+/// reasonable length to limit abuse surface.
+fn sanitize_prompt_field(value: &str) -> String {
+    const MAX_LEN: usize = 128;
+    value
+        .chars()
+        .filter(|&c| c != '\n' && c != '\r')
+        .take(MAX_LEN)
+        .map(|c| if c == '`' { '\'' } else { c })
+        .collect()
+}
+
 fn build_lightweight_prompt(
     prompt: &str,
     context_parts: &[String],
@@ -1323,14 +1375,16 @@ fn build_lightweight_prompt(
         );
 
         if let Some(channel) = notify.channel.as_deref() {
+            let sanitized = sanitize_prompt_field(channel);
             full_prompt.push_str(&format!(
-                "The configured delivery channel for this routine is `{channel}`.\n"
+                "The configured delivery channel for this routine is `{sanitized}`.\n"
             ));
         }
 
         if let Some(user) = notify.user.as_deref() {
+            let sanitized = sanitize_prompt_field(user);
             full_prompt.push_str(&format!(
-                "The configured delivery target for this routine is `{user}`.\n"
+                "The configured delivery target for this routine is `{sanitized}`.\n"
             ));
         }
 
@@ -1766,6 +1820,13 @@ pub fn spawn_cron_ticker(
         engine.check_cron_triggers().await;
 
         let mut ticker = tokio::time::interval(interval);
+        ticker.set_missed_tick_behavior(tokio::time::MissedTickBehavior::Skip);
+        // Periodic event cache refresh so web/CLI mutations are picked up
+        // without requiring tool-path code to call refresh_event_cache().
+        // Uses wall-clock elapsed time so the refresh cadence is stable
+        // regardless of the cron tick interval configuration.
+        let refresh_interval = Duration::from_secs(60);
+        let mut last_refresh = tokio::time::Instant::now();
 
         loop {
             ticker.tick().await;
@@ -1773,7 +1834,11 @@ pub fn spawn_cron_ticker(
             // never races with FullJobWatcher instances from this process.
             engine.sync_dispatched_runs().await;
             engine.check_cron_triggers().await;
-            engine.sync_dispatched_runs().await;
+
+            if last_refresh.elapsed() >= refresh_interval {
+                engine.refresh_event_cache().await;
+                last_refresh = tokio::time::Instant::now();
+            }
         }
     })
 }
@@ -1839,7 +1904,13 @@ fn strip_html_tags(s: &str) -> String {
 
 #[cfg(test)]
 mod tests {
-    use crate::agent::routine::{NotifyConfig, RunStatus};
+    use chrono::Utc;
+    use uuid::Uuid;
+
+    use crate::agent::routine::{
+        NotifyConfig, Routine, RoutineAction, RoutineGuardrails, RunStatus, Trigger,
+    };
+    use crate::channels::IncomingMessage;
     use crate::config::RoutineConfig;
 
     #[test]
@@ -2037,6 +2108,117 @@ mod tests {
         }
     }
 
+    /// Helper to build a test routine with the given user_id and trigger.
+    fn make_routine(user_id: &str, trigger: Trigger) -> Routine {
+        Routine {
+            id: Uuid::new_v4(),
+            name: "test".to_string(),
+            description: String::new(),
+            user_id: user_id.to_string(),
+            enabled: true,
+            trigger,
+            action: RoutineAction::Lightweight {
+                prompt: String::new(),
+                context_paths: vec![],
+                max_tokens: 1000,
+                use_tools: false,
+                max_tool_rounds: 0,
+            },
+            guardrails: RoutineGuardrails::default(),
+            notify: Default::default(),
+            last_run_at: None,
+            next_fire_at: None,
+            run_count: 0,
+            consecutive_failures: 0,
+            state: serde_json::Value::Null,
+            created_at: Utc::now(),
+            updated_at: Utc::now(),
+        }
+    }
+
+    /// Helper to build a test IncomingMessage.
+    fn make_message(user_id: &str, channel: &str, content: &str) -> IncomingMessage {
+        IncomingMessage {
+            id: Uuid::new_v4(),
+            channel: channel.to_string(),
+            user_id: user_id.to_string(),
+            owner_id: user_id.to_string(),
+            sender_id: user_id.to_string(),
+            user_name: None,
+            content: content.to_string(),
+            thread_id: None,
+            conversation_scope_id: None,
+            received_at: Utc::now(),
+            metadata: serde_json::Value::Null,
+            timezone: None,
+            attachments: vec![],
+            is_internal: false,
+        }
+    }
+
+    /// Regression test for issue #1051: event triggers used case-sensitive
+    /// channel comparison, so "Telegram" != "telegram" caused silent mismatch.
+    /// Tests the actual `routine_matches_message` function used in `check_event_triggers`.
+    #[test]
+    fn test_channel_filter_is_case_insensitive() {
+        let routine = make_routine(
+            "user1",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: Some("Telegram".to_string()),
+            },
+        );
+        let msg = make_message("user1", "telegram", "hello");
+
+        // Case-insensitive channel match must succeed
+        assert!(super::routine_matches_message(&routine, &msg));
+
+        // Exact case must also work
+        let msg_exact = make_message("user1", "Telegram", "hello");
+        assert!(super::routine_matches_message(&routine, &msg_exact));
+
+        // Different channel must not match
+        let msg_wrong = make_message("user1", "discord", "hello");
+        assert!(!super::routine_matches_message(&routine, &msg_wrong));
+    }
+
+    /// Regression test for issue #1051: event triggers did not filter by
+    /// user_id, so routines from user A could fire on messages from user B.
+    /// Tests the actual `routine_matches_message` function used in `check_event_triggers`.
+    #[test]
+    fn test_event_trigger_requires_user_match() {
+        let routine = make_routine(
+            "alice",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: None,
+            },
+        );
+
+        // Different user must not match
+        let msg_bob = make_message("bob", "telegram", "hello");
+        assert!(!super::routine_matches_message(&routine, &msg_bob));
+
+        // Same user must match
+        let msg_alice = make_message("alice", "telegram", "hello");
+        assert!(super::routine_matches_message(&routine, &msg_alice));
+    }
+
+    /// When no channel filter is set, any channel should match (given user matches).
+    #[test]
+    fn test_no_channel_filter_matches_any_channel() {
+        let routine = make_routine(
+            "user1",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: None,
+            },
+        );
+
+        let msg = make_message("user1", "whatever_channel", "hello");
+        assert!(super::routine_matches_message(&routine, &msg));
+    }
+
     #[test]
     fn test_routine_tool_denylist_blocks_self_management_tools() {
         let denylisted = vec![

src/agent/scheduler.rs

@@ -9,7 +9,6 @@ use tokio::task::JoinHandle;
 use uuid::Uuid;
 
 use crate::agent::task::{Task, TaskContext, TaskOutput};
-use crate::channels::web::types::SseEvent;
 use crate::config::AgentConfig;
 use crate::context::{ContextManager, JobContext, JobState};
 use crate::db::Database;
@@ -67,8 +66,8 @@ pub struct Scheduler {
     extension_manager: Option<Arc<ExtensionManager>>,
     store: Option<Arc<dyn Database>>,
     hooks: Arc<HookRegistry>,
-    /// SSE broadcast sender for live job event streaming.
-    sse_tx: Option<tokio::sync::broadcast::Sender<SseEvent>>,
+    /// SSE manager for live job event streaming.
+    sse_tx: Option<Arc<crate::channels::web::sse::SseManager>>,
     /// HTTP interceptor for trace recording/replay (propagated to workers).
     http_interceptor: Option<Arc<dyn crate::llm::recording::HttpInterceptor>>,
     /// Running jobs (main LLM-driven jobs).
@@ -102,9 +101,9 @@ impl Scheduler {
         }
     }
 
-    /// Set the SSE broadcast sender for live job event streaming.
-    pub fn set_sse_sender(&mut self, tx: tokio::sync::broadcast::Sender<SseEvent>) {
-        self.sse_tx = Some(tx);
+    /// Set the SSE manager for live job event streaming.
+    pub fn set_sse_sender(&mut self, sse: Arc<crate::channels::web::sse::SseManager>) {
+        self.sse_tx = Some(sse);
     }
 
     /// Set the HTTP interceptor for trace recording/replay.

src/agent/session_manager.rs

@@ -102,11 +102,30 @@ impl SessionManager {
     /// Resolve an external thread ID to an internal thread.
     ///
     /// Returns the session and thread ID. Creates both if they don't exist.
+    /// Delegates to [`resolve_thread_with_parsed_uuid`](Self::resolve_thread_with_parsed_uuid)
+    /// with `parsed_uuid: None`.
     pub async fn resolve_thread(
         &self,
         user_id: &str,
         channel: &str,
         external_thread_id: Option<&str>,
+    ) -> (Arc<Mutex<Session>>, Uuid) {
+        self.resolve_thread_with_parsed_uuid(user_id, channel, external_thread_id, None)
+            .await
+    }
+
+    /// Like [`resolve_thread`](Self::resolve_thread), but accepts a pre-parsed
+    /// UUID to skip redundant parsing when the caller has already validated
+    /// the external thread ID as a UUID (e.g. the approval routing path).
+    ///
+    /// Uses a single read-lock acquisition for both the key lookup and the UUID
+    /// adoption check to reduce contention under concurrent approval load.
+    pub async fn resolve_thread_with_parsed_uuid(
+        &self,
+        user_id: &str,
+        channel: &str,
+        external_thread_id: Option<&str>,
+        parsed_uuid: Option<Uuid>,
     ) -> (Arc<Mutex<Session>>, Uuid) {
         let session = self.get_or_create_session(user_id).await;
 
@@ -116,51 +135,65 @@ impl SessionManager {
             external_thread_id: external_thread_id.map(String::from),
         };
 
-        // Check if we have a mapping
-        {
+        // Use pre-parsed UUID if available, otherwise parse from string.
+        let ext_uuid = parsed_uuid
+            .or_else(|| external_thread_id.and_then(|ext_tid| Uuid::parse_str(ext_tid).ok()));
+
+        // Validate that parsed_uuid (if provided) is consistent with external_thread_id.
+        #[cfg(debug_assertions)]
+        if let (Some(parsed), Some(ext_tid)) = (&parsed_uuid, external_thread_id) {
+            debug_assert_eq!(
+                Uuid::parse_str(ext_tid).ok().as_ref(),
+                Some(parsed),
+                "parsed_uuid must be the parsed form of external_thread_id"
+            );
+        }
+
+        // Single read lock for both the key lookup and UUID adoption check
+        let adoptable_uuid = {
             let thread_map = self.thread_map.read().await;
+
+            // Fast path: exact key match
             if let Some(&thread_id) = thread_map.get(&key) {
-                // Verify thread still exists in session
                 let sess = session.lock().await;
                 if sess.threads.contains_key(&thread_id) {
                     return (Arc::clone(&session), thread_id);
                 }
             }
-        }
 
-        // Check if external_thread_id is itself a known thread UUID that
-        // exists in the session but was never registered in the thread_map
-        // (e.g. created by chat_new_thread_handler or hydrated from DB).
-        // We only adopt it if no thread_map entry maps to this UUID —
-        // otherwise it belongs to a different channel scope.
-        if let Some(ext_tid) = external_thread_id
-            && let Ok(ext_uuid) = Uuid::parse_str(ext_tid)
-        {
-            let thread_map = self.thread_map.read().await;
-            let mapped_elsewhere = thread_map.values().any(|&v| v == ext_uuid);
-            drop(thread_map);
+            // UUID adoption check (still under the same read lock).
+            // If external_thread_id is a valid UUID not mapped elsewhere,
+            // it may be a thread created by chat_new_thread_handler or
+            // hydrated from DB that we can adopt.
+            // Only attempt adoption when external_thread_id is Some, preserving
+            // the invariant that None external_thread_id never triggers adoption.
+            if external_thread_id.is_some() {
+                ext_uuid.filter(|&uuid| !thread_map.values().any(|&v| v == uuid))
+            } else {
+                None
+            }
+        }; // Single read lock dropped here
 
-            if !mapped_elsewhere {
-                let sess = session.lock().await;
-                if sess.threads.contains_key(&ext_uuid) {
-                    drop(sess);
+        // If we found an adoptable UUID, verify it exists in session and acquire write lock
+        if let Some(ext_uuid) = adoptable_uuid {
+            let sess = session.lock().await;
+            if sess.threads.contains_key(&ext_uuid) {
+                drop(sess);
 
-                    let mut thread_map = self.thread_map.write().await;
-                    // Re-check after acquiring write lock to prevent race condition
-                    // where another task mapped this UUID between our read and write.
-                    if !thread_map.values().any(|&v| v == ext_uuid) {
-                        thread_map.insert(key, ext_uuid);
-                        drop(thread_map);
-                        // Ensure undo manager exists
-                        let mut undo_managers = self.undo_managers.write().await;
-                        undo_managers
-                            .entry(ext_uuid)
-                            .or_insert_with(|| Arc::new(Mutex::new(UndoManager::new())));
-                        return (session, ext_uuid);
-                    }
-                    // If it was mapped elsewhere while we were unlocked, fall through
-                    // to create a new thread, preserving channel isolation.
+                let mut thread_map = self.thread_map.write().await;
+                // Re-check after acquiring write lock to prevent race condition
+                // where another task mapped this UUID between our read and write.
+                if !thread_map.values().any(|&v| v == ext_uuid) {
+                    thread_map.insert(key, ext_uuid);
+                    drop(thread_map);
+                    // Ensure undo manager exists
+                    let mut undo_managers = self.undo_managers.write().await;
+                    undo_managers
+                        .entry(ext_uuid)
+                        .or_insert_with(|| Arc::new(Mutex::new(UndoManager::new())));
+                    return (session, ext_uuid);
                 }
+                // If mapped elsewhere while unlocked, fall through to create new thread
             }
         }
 
@@ -909,6 +942,44 @@ mod tests {
         }
     }
 
+    #[tokio::test]
+    async fn test_resolve_thread_consolidates_read_path() {
+        // Verify that resolve_thread still correctly handles:
+        // 1. Fast path: key exists in thread_map
+        // 2. UUID adoption: external_thread_id is a UUID in session but not in map
+        // 3. New thread: neither path matches
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+
+        // Case 1: Normal resolution creates thread and maps it
+        let (session1, tid1) = manager
+            .resolve_thread("user1", "chan1", Some("ext-1"))
+            .await;
+        // Resolving again with same key should return same thread (fast path)
+        let (_, tid1_again) = manager
+            .resolve_thread("user1", "chan1", Some("ext-1"))
+            .await;
+        assert_eq!(tid1, tid1_again);
+
+        // Case 2: UUID adoption - insert a thread directly into session
+        let adopted_id = Uuid::new_v4();
+        {
+            let mut sess = session1.lock().await;
+            let thread = Thread::with_id(adopted_id, sess.id);
+            sess.threads.insert(adopted_id, thread);
+        }
+        // Resolve with the UUID as external_thread_id -- should adopt it
+        let (_, resolved) = manager
+            .resolve_thread("user1", "chan1", Some(&adopted_id.to_string()))
+            .await;
+        assert_eq!(resolved, adopted_id);
+
+        // Case 3: Different channel gets different thread
+        let (_, tid2) = manager.resolve_thread("user1", "chan2", None).await;
+        assert_ne!(tid1, tid2);
+    }
+
     #[tokio::test]
     async fn test_resolve_thread_finds_existing_session_thread_by_uuid() {
         use crate::agent::session::{Session, Thread};
@@ -947,4 +1018,88 @@ mod tests {
             "should have exactly 1 thread, not a duplicate"
         );
     }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_pre_parsed_uuid_adopts_thread() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, _) = manager.resolve_thread("user1", "chan1", None).await;
+
+        // Manually insert a thread with a known UUID
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with pre-parsed UUID -- should adopt it without re-parsing
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid(
+                "user1",
+                "chan1",
+                Some(&known_id.to_string()),
+                Some(known_id),
+            )
+            .await;
+        assert_eq!(resolved, known_id);
+    }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_parsed_uuid_none_delegates_to_parse() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, _) = manager.resolve_thread("user2", "chan2", None).await;
+
+        // Insert a thread with a known UUID
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with parsed_uuid=None but a valid UUID string -- should
+        // fall back to parsing the string and still adopt the thread
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid("user2", "chan2", Some(&known_id.to_string()), None)
+            .await;
+        assert_eq!(resolved, known_id);
+    }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_none_external_thread_id_does_not_adopt() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, default_tid) = manager.resolve_thread("user3", "chan3", None).await;
+
+        // Manually insert a thread with a known UUID (simulating a thread
+        // created by chat_new_thread_handler)
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with external_thread_id=None but parsed_uuid=Some.
+        // This should NOT adopt the UUID — the old code prevented adoption
+        // when external_thread_id was None, and we preserve that invariant.
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid("user3", "chan3", None, Some(known_id))
+            .await;
+
+        // Should return the existing default thread, not the injected UUID
+        assert_eq!(
+            resolved, default_tid,
+            "should return existing default thread when external_thread_id is None"
+        );
+        assert_ne!(
+            resolved, known_id,
+            "should NOT adopt UUID when external_thread_id is None"
+        );
+    }
 }

src/agent/thread_ops.rs

@@ -1646,7 +1646,7 @@ impl Agent {
         };
 
         match ext_mgr
-            .configure_token(&pending.extension_name, token)
+            .configure_token(&pending.extension_name, token, &message.user_id)
             .await
         {
             Ok(result) if result.activated => {

src/app.rs

@@ -312,13 +312,7 @@ impl AppBuilder {
             .create_provider(&self.config.llm.nearai.base_url, self.session.clone());
 
         // Register memory tools if database is available
-        let workspace_user_id = self
-            .config
-            .channels
-            .gateway
-            .as_ref()
-            .map(|gw| gw.user_id.as_str())
-            .unwrap_or("default");
+        let workspace_user_id = self.config.owner_id.as_str();
         let workspace = if let Some(ref db) = self.db {
             let emb_cache_config = EmbeddingCacheConfig {
                 max_entries: self.config.embeddings.cache_size,
@@ -327,7 +321,7 @@ impl AppBuilder {
                 .with_search_config(&self.config.search);
 
             if let Some(ref emb) = embeddings {
-                ws = ws.with_embeddings_cached(emb.clone(), emb_cache_config);
+                ws = ws.with_embeddings_cached(emb.clone(), emb_cache_config.clone());
             }
 
             // Wire workspace-level settings (read scopes, memory layers)
@@ -341,7 +335,35 @@ impl AppBuilder {
             }
             ws = ws.with_memory_layers(self.config.workspace.memory_layers.clone());
             let ws = Arc::new(ws);
-            tools.register_memory_tools(Arc::clone(&ws));
+
+            // Detect multi-tenant mode: when GATEWAY_USER_TOKENS is configured,
+            // each authenticated user needs their own workspace scope. Use
+            // WorkspacePool (which implements WorkspaceResolver) to create
+            // per-user workspaces on demand instead of sharing the startup
+            // workspace across all users.
+            let is_multi_tenant = self
+                .config
+                .channels
+                .gateway
+                .as_ref()
+                .is_some_and(|gw| gw.user_tokens.is_some());
+
+            if is_multi_tenant {
+                let pool = Arc::new(crate::channels::web::server::WorkspacePool::new(
+                    Arc::clone(db),
+                    embeddings.clone(),
+                    emb_cache_config,
+                    self.config.search.clone(),
+                    self.config.workspace.clone(),
+                ));
+                tools.register_memory_tools_with_resolver(pool);
+                tracing::info!(
+                    "Memory tools configured with per-user workspace resolver (multi-tenant mode)"
+                );
+            } else {
+                tools.register_memory_tools(Arc::clone(&ws));
+            }
+
             Some(ws)
         } else {
             None

src/channels/wasm/router.rs

@@ -333,6 +333,9 @@ async fn webhook_handler(
 
     let channel_name = channel.channel_name();
 
+    // Track whether any authentication was performed and passed.
+    let mut did_authenticate = false;
+
     // Check if secret is required
     if state.router.requires_secret(channel_name).await {
         // Get the secret header name for this channel (from capabilities or default)
@@ -382,6 +385,7 @@ async fn webhook_handler(
                     );
                 }
                 tracing::debug!(channel = %channel_name, "Webhook secret validated");
+                did_authenticate = true;
             }
             None => {
                 tracing::warn!(
@@ -433,6 +437,7 @@ async fn webhook_handler(
                     );
                 }
                 tracing::debug!(channel = %channel_name, "Ed25519 signature verified");
+                did_authenticate = true;
             }
             _ => {
                 tracing::warn!(
@@ -484,6 +489,7 @@ async fn webhook_handler(
                     );
                 }
                 tracing::debug!(channel = %channel_name, "HMAC-SHA256 signature verified");
+                did_authenticate = true;
             }
             _ => {
                 tracing::warn!(
@@ -510,8 +516,9 @@ async fn webhook_handler(
         })
         .collect();
 
-    // Call the WASM channel
-    let secret_validated = state.router.requires_secret(channel_name).await;
+    // Call the WASM channel. `did_authenticate` was set above by whichever
+    // auth guard (secret / Ed25519 / HMAC) successfully validated the request.
+    let secret_validated = did_authenticate;
 
     tracing::info!(
         channel = %channel_name,

src/channels/web/auth.rs

@@ -1,17 +1,133 @@
 //! Bearer token authentication middleware for the web gateway.
+//!
+//! Supports multi-user mode: each token maps to a `UserIdentity` that carries
+//! the user_id. The identity is inserted into request extensions so downstream
+//! handlers can extract it via `AuthenticatedUser`.
+
+use std::collections::HashMap;
 
 use axum::{
-    extract::{Request, State},
-    http::{HeaderMap, Method, StatusCode},
+    extract::{FromRequestParts, Request, State},
+    http::{HeaderMap, Method, StatusCode, request::Parts},
     middleware::Next,
     response::{IntoResponse, Response},
 };
+use sha2::{Digest, Sha256};
 use subtle::ConstantTimeEq;
 
-/// Shared auth state injected via axum middleware state.
+/// Identity resolved from a bearer token.
+#[derive(Debug, Clone)]
+pub struct UserIdentity {
+    pub user_id: String,
+    /// Additional user scopes this identity can read from.
+    pub workspace_read_scopes: Vec<String>,
+}
+
+/// Hash a token with SHA-256 for constant-size, timing-safe storage.
+fn hash_token(token: &str) -> [u8; 32] {
+    let mut hasher = Sha256::new();
+    hasher.update(token.as_bytes());
+    hasher.finalize().into()
+}
+
+/// Multi-user auth state: maps token hashes to user identities.
+///
+/// Tokens are SHA-256 hashed on construction so they are never stored in
+/// plaintext. Authentication compares fixed-size (32-byte) digests using
+/// constant-time comparison, eliminating both length-oracle timing leaks
+/// and accidental token exposure in memory dumps.
+///
+/// In single-user mode (the default), contains exactly one entry.
 #[derive(Clone)]
-pub struct AuthState {
-    pub token: String,
+pub struct MultiAuthState {
+    /// Maps SHA-256(token) → identity. Tokens are never stored in cleartext.
+    hashed_tokens: Vec<([u8; 32], UserIdentity)>,
+    /// Original first token kept only for single-user startup printing.
+    /// Not used for authentication.
+    display_token: Option<String>,
+}
+
+impl MultiAuthState {
+    /// Create a single-user auth state (backwards compatible).
+    pub fn single(token: String, user_id: String) -> Self {
+        let hash = hash_token(&token);
+        Self {
+            hashed_tokens: vec![(
+                hash,
+                UserIdentity {
+                    user_id,
+                    workspace_read_scopes: Vec::new(),
+                },
+            )],
+            display_token: Some(token),
+        }
+    }
+
+    /// Create a multi-user auth state from a map of tokens to identities.
+    pub fn multi(tokens: HashMap<String, UserIdentity>) -> Self {
+        let hashed_tokens: Vec<([u8; 32], UserIdentity)> = tokens
+            .into_iter()
+            .map(|(tok, identity)| (hash_token(&tok), identity))
+            .collect();
+        Self {
+            hashed_tokens,
+            display_token: None,
+        }
+    }
+
+    /// Authenticate a token, returning the associated identity if valid.
+    ///
+    /// Uses SHA-256 hashing + constant-time comparison (`subtle::ConstantTimeEq`)
+    /// to prevent timing side-channels. Both the candidate and stored tokens are
+    /// hashed to 32-byte digests, eliminating length-oracle leaks. Iterates all
+    /// entries regardless of match to avoid early-exit timing differences.
+    /// O(n) in the number of configured users — negligible for typical
+    /// deployments (< 10 users).
+    pub fn authenticate(&self, candidate: &str) -> Option<&UserIdentity> {
+        let candidate_hash = hash_token(candidate);
+        let mut matched: Option<&UserIdentity> = None;
+        for (stored_hash, identity) in &self.hashed_tokens {
+            if bool::from(candidate_hash.ct_eq(stored_hash)) {
+                matched = Some(identity);
+            }
+        }
+        matched
+    }
+
+    /// Get the first token for backwards-compatible printing at startup.
+    ///
+    /// Only available in single-user mode; returns `None` in multi-user mode
+    /// to avoid exposing tokens.
+    pub fn first_token(&self) -> Option<&str> {
+        self.display_token.as_deref()
+    }
+
+    /// Get the first user identity (for single-user fallback).
+    pub fn first_identity(&self) -> Option<&UserIdentity> {
+        self.hashed_tokens.first().map(|(_, id)| id)
+    }
+}
+
+/// Axum extractor that provides the authenticated user identity.
+///
+/// Only available on routes behind `auth_middleware`. Extracts the
+/// `UserIdentity` that the middleware inserted into request extensions.
+pub struct AuthenticatedUser(pub UserIdentity);
+
+impl<S> FromRequestParts<S> for AuthenticatedUser
+where
+    S: Send + Sync,
+{
+    type Rejection = (StatusCode, &'static str);
+
+    async fn from_request_parts(parts: &mut Parts, _state: &S) -> Result<Self, Self::Rejection> {
+        parts
+            .extensions
+            .get::<UserIdentity>()
+            .cloned()
+            .map(AuthenticatedUser)
+            .ok_or((StatusCode::UNAUTHORIZED, "Not authenticated"))
+    }
 }
 
 /// Whether query-string token auth is allowed for this request.
@@ -51,29 +167,34 @@ fn query_token(request: &Request) -> Option<String> {
 /// Auth middleware that validates bearer token from header or query param.
 ///
 /// SSE connections can't set headers from `EventSource`, so we also accept
-/// `?token=xxx` as a query parameter, but only on SSE endpoints.
+/// `?token=xxx` as a query parameter, but only on SSE/WS endpoints.
+///
+/// On successful authentication, inserts the matching `UserIdentity` into
+/// request extensions for downstream extraction via `AuthenticatedUser`.
 pub async fn auth_middleware(
-    State(auth): State<AuthState>,
+    State(auth): State<MultiAuthState>,
     headers: HeaderMap,
-    request: Request,
+    mut request: Request,
     next: Next,
 ) -> Response {
-    // Try Authorization header first (constant-time comparison).
+    // Try Authorization header first.
     // RFC 6750 Section 2.1: auth-scheme comparison is case-insensitive.
     if let Some(auth_header) = headers.get("authorization")
         && let Ok(value) = auth_header.to_str()
         && value.len() > 7
         && value[..7].eq_ignore_ascii_case("Bearer ")
-        && bool::from(value.as_bytes()[7..].ct_eq(auth.token.as_bytes()))
+        && let Some(identity) = auth.authenticate(&value[7..])
     {
+        request.extensions_mut().insert(identity.clone());
         return next.run(request).await;
     }
 
-    // Fall back to query parameter, but only for SSE endpoints (constant-time comparison).
+    // Fall back to query parameter, but only for SSE/WS endpoints.
     if allows_query_token_auth(&request)
         && let Some(token) = query_token(&request)
-        && bool::from(token.as_bytes().ct_eq(auth.token.as_bytes()))
+        && let Some(identity) = auth.authenticate(&token)
     {
+        request.extensions_mut().insert(identity.clone());
         return next.run(request).await;
     }
 
@@ -83,15 +204,61 @@ pub async fn auth_middleware(
 #[cfg(test)]
 mod tests {
     use super::*;
-    use crate::testing::credentials::{TEST_AUTH_SECRET_TOKEN, TEST_BEARER_TOKEN};
+    use crate::testing::credentials::TEST_AUTH_SECRET_TOKEN;
 
     #[test]
-    fn test_auth_state_clone() {
-        let state = AuthState {
-            token: TEST_BEARER_TOKEN.to_string(),
-        };
-        let cloned = state.clone();
-        assert_eq!(cloned.token, TEST_BEARER_TOKEN);
+    fn test_multi_auth_state_single() {
+        let state = MultiAuthState::single("tok-123".to_string(), "alice".to_string());
+        let identity = state.authenticate("tok-123");
+        assert!(identity.is_some());
+        assert_eq!(identity.unwrap().user_id, "alice");
+    }
+
+    #[test]
+    fn test_multi_auth_state_reject_wrong_token() {
+        let state = MultiAuthState::single("tok-123".to_string(), "alice".to_string());
+        assert!(state.authenticate("wrong-token").is_none());
+    }
+
+    #[test]
+    fn test_multi_auth_state_multi_users() {
+        let mut tokens = HashMap::new();
+        tokens.insert(
+            "tok-alice".to_string(),
+            UserIdentity {
+                user_id: "alice".to_string(),
+                workspace_read_scopes: Vec::new(),
+            },
+        );
+        tokens.insert(
+            "tok-bob".to_string(),
+            UserIdentity {
+                user_id: "bob".to_string(),
+                workspace_read_scopes: Vec::new(),
+            },
+        );
+        let state = MultiAuthState::multi(tokens);
+
+        let alice = state.authenticate("tok-alice").unwrap();
+        assert_eq!(alice.user_id, "alice");
+
+        let bob = state.authenticate("tok-bob").unwrap();
+        assert_eq!(bob.user_id, "bob");
+
+        assert!(state.authenticate("tok-charlie").is_none());
+    }
+
+    #[test]
+    fn test_multi_auth_state_first_token() {
+        let state = MultiAuthState::single("my-token".to_string(), "user1".to_string());
+        assert_eq!(state.first_token(), Some("my-token"));
+    }
+
+    #[test]
+    fn test_multi_auth_state_first_identity() {
+        let state = MultiAuthState::single("my-token".to_string(), "user1".to_string());
+        let identity = state.first_identity().unwrap();
+        assert_eq!(identity.user_id, "user1");
     }
 
     use axum::Router;
@@ -107,9 +274,7 @@ mod tests {
     /// Router with streaming endpoints (query auth allowed) and regular
     /// endpoints (query auth rejected).
     fn test_app(token: &str) -> Router {
-        let state = AuthState {
-            token: token.to_string(),
-        };
+        let state = MultiAuthState::single(token.to_string(), "test-user".to_string());
         Router::new()
             .route("/api/chat/events", get(dummy_handler))
             .route("/api/logs/events", get(dummy_handler))
@@ -306,4 +471,200 @@ mod tests {
         let resp = app.oneshot(req).await.unwrap();
         assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
     }
+
+    // --- Multi-tenant auth integration tests ---
+
+    /// Handler that extracts `AuthenticatedUser` and returns the resolved user_id.
+    async fn identity_handler(AuthenticatedUser(identity): AuthenticatedUser) -> String {
+        identity.user_id
+    }
+
+    /// Handler that extracts `AuthenticatedUser` and returns workspace_read_scopes as JSON.
+    async fn scopes_handler(AuthenticatedUser(identity): AuthenticatedUser) -> String {
+        serde_json::to_string(&identity.workspace_read_scopes).unwrap()
+    }
+
+    /// Build a multi-user router where each token maps to a distinct identity.
+    fn multi_user_app(tokens: HashMap<String, UserIdentity>) -> Router {
+        let state = MultiAuthState::multi(tokens);
+        Router::new()
+            .route("/api/chat/events", get(identity_handler))
+            .route("/api/chat/send", post(identity_handler))
+            .route("/api/scopes", get(scopes_handler))
+            .layer(middleware::from_fn_with_state(state, auth_middleware))
+    }
+
+    fn two_user_tokens() -> HashMap<String, UserIdentity> {
+        let mut tokens = HashMap::new();
+        tokens.insert(
+            "tok-alice".to_string(),
+            UserIdentity {
+                user_id: "alice".to_string(),
+                workspace_read_scopes: vec!["shared".to_string()],
+            },
+        );
+        tokens.insert(
+            "tok-bob".to_string(),
+            UserIdentity {
+                user_id: "bob".to_string(),
+                workspace_read_scopes: vec!["shared".to_string(), "alice".to_string()],
+            },
+        );
+        tokens
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_alice_token_resolves_to_alice() {
+        let app = multi_user_app(two_user_tokens());
+        let req = Request::builder()
+            .uri("/api/chat/events")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "alice");
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_bob_token_resolves_to_bob() {
+        let app = multi_user_app(two_user_tokens());
+        let req = Request::builder()
+            .uri("/api/chat/events")
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "bob");
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_sequential_tokens_resolve_independently() {
+        // Send both alice and bob tokens sequentially and verify each gets
+        // the correct identity — guards against token map corruption.
+        let tokens = two_user_tokens();
+
+        let app1 = multi_user_app(tokens.clone());
+        let req = Request::builder()
+            .uri("/api/chat/events")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app1.oneshot(req).await.unwrap();
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "alice");
+
+        let app2 = multi_user_app(tokens);
+        let req = Request::builder()
+            .uri("/api/chat/events")
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app2.oneshot(req).await.unwrap();
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "bob");
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_unknown_token_rejected() {
+        let app = multi_user_app(two_user_tokens());
+        let req = Request::builder()
+            .uri("/api/chat/events")
+            .header("Authorization", "Bearer tok-charlie")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_workspace_read_scopes_propagated() {
+        let app = multi_user_app(two_user_tokens());
+
+        // Alice has ["shared"]
+        let req = Request::builder()
+            .uri("/api/scopes")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        let scopes: Vec<String> = serde_json::from_slice(&body).unwrap();
+        assert_eq!(scopes, vec!["shared"]);
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_bob_has_two_scopes() {
+        let app = multi_user_app(two_user_tokens());
+
+        // Bob has ["shared", "alice"]
+        let req = Request::builder()
+            .uri("/api/scopes")
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        let scopes: Vec<String> = serde_json::from_slice(&body).unwrap();
+        assert_eq!(scopes, vec!["shared", "alice"]);
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_query_param_resolves_correct_identity() {
+        let app = multi_user_app(two_user_tokens());
+        let req = Request::builder()
+            .uri("/api/chat/events?token=tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "bob");
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_post_with_bearer_resolves_identity() {
+        let app = multi_user_app(two_user_tokens());
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri("/api/chat/send")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        assert_eq!(body, "alice");
+    }
+
+    #[tokio::test]
+    async fn test_multi_user_empty_scopes_for_single_user() {
+        // Single-user mode creates identity with empty workspace_read_scopes.
+        let state = MultiAuthState::single("tok-only".to_string(), "solo".to_string());
+        let app = Router::new()
+            .route("/api/scopes", get(scopes_handler))
+            .layer(middleware::from_fn_with_state(state, auth_middleware));
+        let req = Request::builder()
+            .uri("/api/scopes")
+            .header("Authorization", "Bearer tok-only")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        let body = axum::body::to_bytes(resp.into_body(), 1024).await.unwrap();
+        let scopes: Vec<String> = serde_json::from_slice(&body).unwrap();
+        assert!(scopes.is_empty());
+    }
+
+    #[tokio::test]
+    async fn test_prefix_and_extension_tokens_rejected() {
+        // Verifies that prefix/suffix variants of valid tokens are rejected.
+        // Note: the constant-time property is enforced structurally by use of
+        // subtle::ConstantTimeEq and cannot be verified via outcome testing.
+        let state = MultiAuthState::single("long-secret-token".to_string(), "user".to_string());
+        assert!(state.authenticate("long-secret").is_none());
+        assert!(state.authenticate("long-secret-token-extra").is_none());
+    }
 }

src/channels/web/handlers/chat.rs

@@ -12,22 +12,24 @@ use serde::Deserialize;
 use uuid::Uuid;
 
 use crate::channels::IncomingMessage;
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 use crate::channels::web::util::{build_turns_from_db_messages, truncate_preview};
 
 pub async fn chat_send_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
     Json(req): Json<SendMessageRequest>,
 ) -> Result<(StatusCode, Json<SendMessageResponse>), (StatusCode, String)> {
-    if !state.chat_rate_limiter.check() {
+    if !state.chat_rate_limiter.check(&identity.user_id) {
         return Err((
             StatusCode::TOO_MANY_REQUESTS,
             "Rate limit exceeded. Try again shortly.".to_string(),
         ));
     }
 
-    let mut msg = IncomingMessage::new("gateway", &state.user_id, &req.content);
+    let mut msg = IncomingMessage::new("gateway", &identity.user_id, &req.content);
 
     if let Some(ref thread_id) = req.thread_id {
         msg = msg.with_thread(thread_id);
@@ -74,6 +76,7 @@ pub async fn chat_send_handler(
 
 pub async fn chat_approval_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
     Json(req): Json<ApprovalRequest>,
 ) -> Result<(StatusCode, Json<SendMessageResponse>), (StatusCode, String)> {
     let (approved, always) = match req.action.as_str() {
@@ -109,7 +112,7 @@ pub async fn chat_approval_handler(
         )
     })?;
 
-    let mut msg = IncomingMessage::new("gateway", &state.user_id, content);
+    let mut msg = IncomingMessage::new("gateway", &identity.user_id, content);
 
     if let Some(ref thread_id) = req.thread_id {
         msg = msg.with_thread(thread_id);
@@ -150,6 +153,7 @@ pub async fn chat_approval_handler(
 /// The token never touches the LLM, chat history, or SSE stream.
 pub async fn chat_auth_token_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Json(req): Json<AuthTokenRequest>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
     let ext_mgr = state.extension_manager.as_ref().ok_or((
@@ -158,7 +162,7 @@ pub async fn chat_auth_token_handler(
     ))?;
 
     match ext_mgr
-        .configure_token(&req.extension_name, &req.token)
+        .configure_token(&req.extension_name, &req.token, &user.user_id)
         .await
     {
         Ok(result) => {
@@ -169,20 +173,26 @@ pub async fn chat_auth_token_handler(
             resp.instructions = result.verification.as_ref().map(|v| v.instructions.clone());
 
             if result.verification.is_some() {
-                state.sse.broadcast(SseEvent::AuthRequired {
-                    extension_name: req.extension_name.clone(),
-                    instructions: Some(result.message),
-                    auth_url: None,
-                    setup_url: None,
-                });
+                state.sse.broadcast_for_user(
+                    &user.user_id,
+                    SseEvent::AuthRequired {
+                        extension_name: req.extension_name.clone(),
+                        instructions: Some(result.message),
+                        auth_url: None,
+                        setup_url: None,
+                    },
+                );
             } else {
-                clear_auth_mode(&state).await;
+                clear_auth_mode(&state, &user.user_id).await;
 
-                state.sse.broadcast(SseEvent::AuthCompleted {
-                    extension_name: req.extension_name.clone(),
-                    success: true,
-                    message: result.message,
-                });
+                state.sse.broadcast_for_user(
+                    &user.user_id,
+                    SseEvent::AuthCompleted {
+                        extension_name: req.extension_name.clone(),
+                        success: true,
+                        message: result.message,
+                    },
+                );
             }
 
             Ok(Json(resp))
@@ -190,12 +200,15 @@ pub async fn chat_auth_token_handler(
         Err(e) => {
             let msg = e.to_string();
             if matches!(e, crate::extensions::ExtensionError::ValidationFailed(_)) {
-                state.sse.broadcast(SseEvent::AuthRequired {
-                    extension_name: req.extension_name.clone(),
-                    instructions: Some(msg.clone()),
-                    auth_url: None,
-                    setup_url: None,
-                });
+                state.sse.broadcast_for_user(
+                    &user.user_id,
+                    SseEvent::AuthRequired {
+                        extension_name: req.extension_name.clone(),
+                        instructions: Some(msg.clone()),
+                        auth_url: None,
+                        setup_url: None,
+                    },
+                );
             }
             Ok(Json(ActionResponse::fail(msg)))
         }
@@ -205,16 +218,17 @@ pub async fn chat_auth_token_handler(
 /// Cancel an in-progress auth flow.
 pub async fn chat_auth_cancel_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
     Json(_req): Json<AuthCancelRequest>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
-    clear_auth_mode(&state).await;
+    clear_auth_mode(&state, &identity.user_id).await;
     Ok(Json(ActionResponse::ok("Auth cancelled")))
 }
 
 /// Clear pending auth mode on the active thread.
-pub async fn clear_auth_mode(state: &GatewayState) {
+pub async fn clear_auth_mode(state: &GatewayState, user_id: &str) {
     if let Some(ref sm) = state.session_manager {
-        let session = sm.get_or_create_session(&state.user_id).await;
+        let session = sm.get_or_create_session(user_id).await;
         let mut sess = session.lock().await;
         if let Some(thread_id) = sess.active_thread
             && let Some(thread) = sess.threads.get_mut(&thread_id)
@@ -226,8 +240,9 @@ pub async fn clear_auth_mode(state: &GatewayState) {
 
 pub async fn chat_events_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<impl IntoResponse, (StatusCode, String)> {
-    state.sse.subscribe().ok_or((
+    state.sse.subscribe(Some(user.user_id)).ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
         "Too many connections".to_string(),
     ))
@@ -237,6 +252,7 @@ pub async fn chat_ws_handler(
     headers: axum::http::HeaderMap,
     ws: WebSocketUpgrade,
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
 ) -> Result<impl IntoResponse, (StatusCode, String)> {
     // Validate Origin header to prevent cross-site WebSocket hijacking.
     let origin = headers
@@ -262,7 +278,9 @@ pub async fn chat_ws_handler(
             "WebSocket origin not allowed".to_string(),
         ));
     }
-    Ok(ws.on_upgrade(move |socket| crate::channels::web::ws::handle_ws_connection(socket, state)))
+    Ok(ws.on_upgrade(move |socket| {
+        crate::channels::web::ws::handle_ws_connection(socket, state, identity)
+    }))
 }
 
 #[derive(Deserialize)]
@@ -274,6 +292,7 @@ pub struct HistoryQuery {
 
 pub async fn chat_history_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
     Query(query): Query<HistoryQuery>,
 ) -> Result<Json<HistoryResponse>, (StatusCode, String)> {
     let session_manager = state.session_manager.as_ref().ok_or((
@@ -281,7 +300,9 @@ pub async fn chat_history_handler(
         "Session manager not available".to_string(),
     ))?;
 
-    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let session = session_manager
+        .get_or_create_session(&identity.user_id)
+        .await;
 
     let limit = query.limit.unwrap_or(50);
     let before_cursor = query
@@ -314,7 +335,7 @@ pub async fn chat_history_handler(
         && let Some(ref store) = state.store
     {
         let owned = store
-            .conversation_belongs_to_user(thread_id, &state.user_id)
+            .conversation_belongs_to_user(thread_id, &identity.user_id)
             .await
             .unwrap_or(false);
         if !owned {
@@ -434,24 +455,27 @@ pub async fn chat_history_handler(
 
 pub async fn chat_threads_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
 ) -> Result<Json<ThreadListResponse>, (StatusCode, String)> {
     let session_manager = state.session_manager.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
         "Session manager not available".to_string(),
     ))?;
 
-    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let session = session_manager
+        .get_or_create_session(&identity.user_id)
+        .await;
 
     // Try DB first for persistent thread list
     if let Some(ref store) = state.store {
         // Auto-create assistant thread if it doesn't exist
         let assistant_id = store
-            .get_or_create_assistant_conversation(&state.user_id, "gateway")
+            .get_or_create_assistant_conversation(&identity.user_id, "gateway")
             .await
             .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
         if let Ok(summaries) = store
-            .list_conversations_all_channels(&state.user_id, 50)
+            .list_conversations_all_channels(&identity.user_id, 50)
             .await
         {
             let mut assistant_thread = None;
@@ -534,13 +558,16 @@ pub async fn chat_threads_handler(
 
 pub async fn chat_new_thread_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(identity): AuthenticatedUser,
 ) -> Result<Json<ThreadInfo>, (StatusCode, String)> {
     let session_manager = state.session_manager.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
         "Session manager not available".to_string(),
     ))?;
 
-    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let session = session_manager
+        .get_or_create_session(&identity.user_id)
+        .await;
     let (thread_id, info) = {
         let mut sess = session.lock().await;
         let thread = sess.create_thread();
@@ -562,12 +589,12 @@ pub async fn chat_new_thread_handler(
     // so that the subsequent loadThreads() call from the frontend sees it.
     if let Some(ref store) = state.store {
         match store
-            .ensure_conversation(thread_id, "gateway", &state.user_id, None)
+            .ensure_conversation(thread_id, "gateway", &identity.user_id, None)
             .await
         {
             Ok(true) => {}
             Ok(false) => tracing::warn!(
-                user = %state.user_id,
+                user = %identity.user_id,
                 thread_id = %thread_id,
                 "Skipped persisting new thread due to ownership/channel conflict"
             ),

src/channels/web/handlers/extensions.rs

@@ -8,11 +8,13 @@ use axum::{
     http::StatusCode,
 };
 
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 
 pub async fn extensions_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<ExtensionListResponse>, (StatusCode, String)> {
     let ext_mgr = state.extension_manager.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
@@ -20,7 +22,7 @@ pub async fn extensions_list_handler(
     ))?;
 
     let installed = ext_mgr
-        .list(None, false)
+        .list(None, false, &user.user_id)
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
@@ -80,6 +82,7 @@ pub async fn extensions_list_handler(
 
 pub async fn extensions_tools_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(_user): AuthenticatedUser,
 ) -> Result<Json<ToolListResponse>, (StatusCode, String)> {
     let registry = state.tool_registry.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
@@ -100,6 +103,7 @@ pub async fn extensions_tools_handler(
 
 pub async fn extensions_install_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Json(req): Json<InstallExtensionRequest>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
     let ext_mgr = state.extension_manager.as_ref().ok_or((
@@ -116,7 +120,7 @@ pub async fn extensions_install_handler(
     });
 
     match ext_mgr
-        .install(&req.name, req.url.as_deref(), kind_hint)
+        .install(&req.name, req.url.as_deref(), kind_hint, &user.user_id)
         .await
     {
         Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
@@ -126,6 +130,7 @@ pub async fn extensions_install_handler(
 
 pub async fn extensions_remove_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
     let ext_mgr = state.extension_manager.as_ref().ok_or((
@@ -133,7 +138,7 @@ pub async fn extensions_remove_handler(
         "Extension manager not available (secrets store required)".to_string(),
     ))?;
 
-    match ext_mgr.remove(&name).await {
+    match ext_mgr.remove(&name, &user.user_id).await {
         Ok(message) => Ok(Json(ActionResponse::ok(message))),
         Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
     }

src/channels/web/handlers/jobs.rs

@@ -11,11 +11,13 @@ use axum::{
 use serde::Deserialize;
 use uuid::Uuid;
 
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 
 pub async fn jobs_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<JobListResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
@@ -25,8 +27,8 @@ pub async fn jobs_list_handler(
     let mut jobs: Vec<JobInfo> = Vec::new();
     let mut seen_ids: HashSet<Uuid> = HashSet::new();
 
-    // Fetch sandbox jobs from database.
-    match store.list_sandbox_jobs().await {
+    // Fetch sandbox jobs scoped to this user.
+    match store.list_sandbox_jobs_for_user(&user.user_id).await {
         Ok(sandbox_jobs) => {
             for j in &sandbox_jobs {
                 let ui_state = match j.status.as_str() {
@@ -50,8 +52,8 @@ pub async fn jobs_list_handler(
         }
     }
 
-    // Fetch agent (non-sandbox) jobs from database, deduplicating by ID.
-    match store.list_agent_jobs().await {
+    // Fetch agent (non-sandbox) jobs scoped to this user, deduplicating by ID.
+    match store.list_agent_jobs_for_user(&user.user_id).await {
         Ok(agent_jobs) => {
             for j in &agent_jobs {
                 if seen_ids.contains(&j.id) {
@@ -80,6 +82,7 @@ pub async fn jobs_list_handler(
 
 pub async fn jobs_summary_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<JobSummaryResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
@@ -93,8 +96,8 @@ pub async fn jobs_summary_handler(
     let mut failed = 0;
     let mut stuck = 0;
 
-    // Sandbox job counts.
-    match store.sandbox_job_summary().await {
+    // Sandbox job counts scoped to this user.
+    match store.sandbox_job_summary_for_user(&user.user_id).await {
         Ok(s) => {
             total += s.total;
             pending += s.creating;
@@ -107,8 +110,8 @@ pub async fn jobs_summary_handler(
         }
     }
 
-    // Agent job counts.
-    match store.agent_job_summary().await {
+    // Agent job counts scoped to this user.
+    match store.agent_job_summary_for_user(&user.user_id).await {
         Ok(s) => {
             total += s.total;
             pending += s.pending;
@@ -134,6 +137,7 @@ pub async fn jobs_summary_handler(
 
 pub async fn jobs_detail_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<JobDetailResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -145,169 +149,213 @@ pub async fn jobs_detail_handler(
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
 
     // Try sandbox job from DB first.
-    if let Ok(Some(job)) = store.get_sandbox_job(job_id).await {
-        let browse_id = std::path::Path::new(&job.project_dir)
-            .file_name()
-            .map(|n| n.to_string_lossy().to_string())
-            .unwrap_or_else(|| job.id.to_string());
+    match store.get_sandbox_job(job_id).await {
+        Ok(Some(job)) => {
+            if job.user_id != user.user_id {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+            let browse_id = std::path::Path::new(&job.project_dir)
+                .file_name()
+                .map(|n| n.to_string_lossy().to_string())
+                .unwrap_or_else(|| job.id.to_string());
 
-        let ui_state = match job.status.as_str() {
-            "creating" => "pending",
-            "running" => "in_progress",
-            s => s,
-        };
+            let ui_state = match job.status.as_str() {
+                "creating" => "pending",
+                "running" => "in_progress",
+                s => s,
+            };
 
-        let elapsed_secs = job.started_at.map(|start| {
-            let end = job.completed_at.unwrap_or_else(chrono::Utc::now);
-            (end - start).num_seconds().max(0) as u64
-        });
-
-        // Synthesize transitions from timestamps.
-        let mut transitions = Vec::new();
-        if let Some(started) = job.started_at {
-            transitions.push(TransitionInfo {
-                from: "creating".to_string(),
-                to: "running".to_string(),
-                timestamp: started.to_rfc3339(),
-                reason: None,
+            let elapsed_secs = job.started_at.map(|start| {
+                let end = job.completed_at.unwrap_or_else(chrono::Utc::now);
+                (end - start).num_seconds().max(0) as u64
             });
-        }
-        if let Some(completed) = job.completed_at {
-            transitions.push(TransitionInfo {
-                from: "running".to_string(),
-                to: job.status.clone(),
-                timestamp: completed.to_rfc3339(),
-                reason: job.failure_reason.clone(),
-            });
-        }
 
-        let mode = store.get_sandbox_job_mode(job.id).await.ok().flatten();
-        let is_claude_code = mode.as_deref() == Some("claude_code");
+            // Synthesize transitions from timestamps.
+            let mut transitions = Vec::new();
+            if let Some(started) = job.started_at {
+                transitions.push(TransitionInfo {
+                    from: "creating".to_string(),
+                    to: "running".to_string(),
+                    timestamp: started.to_rfc3339(),
+                    reason: None,
+                });
+            }
+            if let Some(completed) = job.completed_at {
+                transitions.push(TransitionInfo {
+                    from: "running".to_string(),
+                    to: job.status.clone(),
+                    timestamp: completed.to_rfc3339(),
+                    reason: job.failure_reason.clone(),
+                });
+            }
 
-        return Ok(Json(JobDetailResponse {
-            id: job.id,
-            title: job.task.clone(),
-            description: String::new(),
-            state: ui_state.to_string(),
-            user_id: job.user_id.clone(),
-            created_at: job.created_at.to_rfc3339(),
-            started_at: job.started_at.map(|dt| dt.to_rfc3339()),
-            completed_at: job.completed_at.map(|dt| dt.to_rfc3339()),
-            elapsed_secs,
-            project_dir: Some(job.project_dir.clone()),
-            browse_url: Some(format!("/projects/{}/", browse_id)),
-            job_mode: mode.filter(|m| m != "worker"),
-            transitions,
-            can_restart: state.job_manager.is_some(),
-            can_prompt: is_claude_code && state.prompt_queue.is_some(),
-            job_kind: Some("sandbox".to_string()),
-        }));
+            let mode = store.get_sandbox_job_mode(job.id).await.ok().flatten();
+            let is_claude_code = mode.as_deref() == Some("claude_code");
+
+            return Ok(Json(JobDetailResponse {
+                id: job.id,
+                title: job.task.clone(),
+                description: String::new(),
+                state: ui_state.to_string(),
+                user_id: job.user_id.clone(),
+                created_at: job.created_at.to_rfc3339(),
+                started_at: job.started_at.map(|dt| dt.to_rfc3339()),
+                completed_at: job.completed_at.map(|dt| dt.to_rfc3339()),
+                elapsed_secs,
+                project_dir: Some(job.project_dir.clone()),
+                browse_url: Some(format!("/projects/{}/", browse_id)),
+                job_mode: mode.filter(|m| m != "worker"),
+                transitions,
+                can_restart: state.job_manager.is_some(),
+                can_prompt: is_claude_code && state.prompt_queue.is_some(),
+                job_kind: Some("sandbox".to_string()),
+            }));
+        }
+        Ok(None) => {}
+        Err(e) => {
+            return Err((
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Database error: {}", e),
+            ));
+        }
     }
 
     // Fall back to agent job from DB.
-    if let Ok(Some(ctx)) = store.get_job(job_id).await {
-        let elapsed_secs = ctx.started_at.map(|start| {
-            let end = ctx.completed_at.unwrap_or_else(chrono::Utc::now);
-            (end - start).num_seconds().max(0) as u64
-        });
+    match store.get_job(job_id).await {
+        Ok(Some(ctx)) => {
+            if ctx.user_id != user.user_id {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+            let elapsed_secs = ctx.started_at.map(|start| {
+                let end = ctx.completed_at.unwrap_or_else(chrono::Utc::now);
+                (end - start).num_seconds().max(0) as u64
+            });
 
-        // Only show prompt bar for jobs that have a running worker (Pending/InProgress).
-        // Stuck jobs have no active worker loop, so messages would be silently dropped.
-        let is_promptable = matches!(
-            ctx.state,
-            crate::context::JobState::Pending | crate::context::JobState::InProgress
-        );
-        return Ok(Json(JobDetailResponse {
-            id: ctx.job_id,
-            title: ctx.title.clone(),
-            description: ctx.description.clone(),
-            state: ctx.state.to_string(),
-            user_id: ctx.user_id.clone(),
-            created_at: ctx.created_at.to_rfc3339(),
-            started_at: ctx.started_at.map(|dt| dt.to_rfc3339()),
-            completed_at: ctx.completed_at.map(|dt| dt.to_rfc3339()),
-            elapsed_secs,
-            project_dir: None,
-            browse_url: None,
-            job_mode: None,
-            transitions: Vec::new(),
-            can_restart: state.scheduler.is_some(),
-            can_prompt: is_promptable && state.scheduler.is_some(),
-            job_kind: Some("agent".to_string()),
-        }));
+            // Only show prompt bar for jobs that have a running worker (Pending/InProgress).
+            // Stuck jobs have no active worker loop, so messages would be silently dropped.
+            let is_promptable = matches!(
+                ctx.state,
+                crate::context::JobState::Pending | crate::context::JobState::InProgress
+            );
+            Ok(Json(JobDetailResponse {
+                id: ctx.job_id,
+                title: ctx.title.clone(),
+                description: ctx.description.clone(),
+                state: ctx.state.to_string(),
+                user_id: ctx.user_id.clone(),
+                created_at: ctx.created_at.to_rfc3339(),
+                started_at: ctx.started_at.map(|dt| dt.to_rfc3339()),
+                completed_at: ctx.completed_at.map(|dt| dt.to_rfc3339()),
+                elapsed_secs,
+                project_dir: None,
+                browse_url: None,
+                job_mode: None,
+                transitions: Vec::new(),
+                can_restart: state.scheduler.is_some(),
+                can_prompt: is_promptable && state.scheduler.is_some(),
+                job_kind: Some("agent".to_string()),
+            }))
+        }
+        Ok(None) => Err((StatusCode::NOT_FOUND, "Job not found".to_string())),
+        Err(e) => Err((
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Database error: {}", e),
+        )),
     }
-
-    Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
 }
 
 pub async fn jobs_cancel_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     let job_id = Uuid::parse_str(&id)
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
 
     // Try sandbox job cancellation.
-    if let Some(ref store) = state.store
-        && let Ok(Some(job)) = store.get_sandbox_job(job_id).await
-    {
-        if job.status == "running" || job.status == "creating" {
-            // Stop the container if we have a job manager.
-            if let Some(ref jm) = state.job_manager
-                && let Err(e) = jm.stop_job(job_id).await
-            {
-                tracing::warn!(job_id = %job_id, error = %e, "Failed to stop container during cancellation");
+    if let Some(ref store) = state.store {
+        match store.get_sandbox_job(job_id).await {
+            Ok(Some(job)) => {
+                if job.user_id != user.user_id {
+                    return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+                }
+                if job.status == "running" || job.status == "creating" {
+                    if let Some(ref jm) = state.job_manager
+                        && let Err(e) = jm.stop_job(job_id).await
+                    {
+                        tracing::warn!(job_id = %job_id, error = %e, "Failed to stop container during cancellation");
+                    }
+                    store
+                        .update_sandbox_job_status(
+                            job_id,
+                            "failed",
+                            Some(false),
+                            Some("Cancelled by user"),
+                            None,
+                            Some(chrono::Utc::now()),
+                        )
+                        .await
+                        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+                }
+                return Ok(Json(serde_json::json!({
+                    "status": "cancelled",
+                    "job_id": job_id,
+                })));
+            }
+            Ok(None) => {}
+            Err(e) => {
+                return Err((
+                    StatusCode::INTERNAL_SERVER_ERROR,
+                    format!("Database error: {}", e),
+                ));
             }
-            store
-                .update_sandbox_job_status(
-                    job_id,
-                    "failed",
-                    Some(false),
-                    Some("Cancelled by user"),
-                    None,
-                    Some(chrono::Utc::now()),
-                )
-                .await
-                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
         }
-        return Ok(Json(serde_json::json!({
-            "status": "cancelled",
-            "job_id": job_id,
-        })));
     }
 
     // Fall back to agent job cancellation: stop the worker via the scheduler
     // (which updates the in-memory ContextManager AND aborts the task handle),
     // then persist the status to the DB as a fallback.
-    if let Some(ref store) = state.store
-        && let Ok(Some(job)) = store.get_job(job_id).await
-    {
-        if job.state.is_active() {
-            // Try to stop via scheduler (aborts the worker task + updates
-            // in-memory ContextManager). This is best-effort — the job may
-            // not be in the scheduler map if it already finished.
-            if let Some(ref slot) = state.scheduler
-                && let Some(ref scheduler) = *slot.read().await
-            {
-                let _ = scheduler.stop(job_id).await;
-            }
+    if let Some(ref store) = state.store {
+        match store.get_job(job_id).await {
+            Ok(Some(job)) => {
+                if job.user_id != user.user_id {
+                    return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+                }
+                if job.state.is_active() {
+                    // Try to stop via scheduler (aborts the worker task + updates
+                    // in-memory ContextManager). This is best-effort — the job may
+                    // not be in the scheduler map if it already finished.
+                    if let Some(ref slot) = state.scheduler
+                        && let Some(ref scheduler) = *slot.read().await
+                    {
+                        let _ = scheduler.stop(job_id).await;
+                    }
 
-            // Always persist cancellation to the DB so the state is
-            // consistent even if the scheduler wasn't available or the
-            // job wasn't in its in-memory map.
-            store
-                .update_job_status(
-                    job_id,
-                    crate::context::JobState::Cancelled,
-                    Some("Cancelled by user"),
-                )
-                .await
-                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+                    // Always persist cancellation to the DB so the state is
+                    // consistent even if the scheduler wasn't available or the
+                    // job wasn't in its in-memory map.
+                    store
+                        .update_job_status(
+                            job_id,
+                            crate::context::JobState::Cancelled,
+                            Some("Cancelled by user"),
+                        )
+                        .await
+                        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+                }
+                return Ok(Json(serde_json::json!({
+                    "status": "cancelled",
+                    "job_id": job_id,
+                })));
+            }
+            Ok(None) => {}
+            Err(e) => {
+                return Err((
+                    StatusCode::INTERNAL_SERVER_ERROR,
+                    format!("Database error: {}", e),
+                ));
+            }
         }
-        return Ok(Json(serde_json::json!({
-            "status": "cancelled",
-            "job_id": job_id,
-        })));
     }
 
     Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
@@ -315,6 +363,7 @@ pub async fn jobs_cancel_handler(
 
 pub async fn jobs_restart_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -326,146 +375,166 @@ pub async fn jobs_restart_handler(
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
 
     // Try sandbox job restart first.
-    if let Ok(Some(old_job)) = store.get_sandbox_job(old_job_id).await {
-        if old_job.status != "interrupted" && old_job.status != "failed" {
+    match store.get_sandbox_job(old_job_id).await {
+        Ok(Some(old_job)) => {
+            if old_job.user_id != user.user_id {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+            if old_job.status != "interrupted" && old_job.status != "failed" {
+                return Err((
+                    StatusCode::CONFLICT,
+                    format!("Cannot restart job in state '{}'", old_job.status),
+                ));
+            }
+
+            let jm = state.job_manager.as_ref().ok_or((
+                StatusCode::SERVICE_UNAVAILABLE,
+                "Sandbox not enabled".to_string(),
+            ))?;
+
+            // Enrich the task with failure context.
+            let task = if let Some(ref reason) = old_job.failure_reason {
+                format!(
+                    "Previous attempt failed: {}. Retry: {}",
+                    reason, old_job.task
+                )
+            } else {
+                old_job.task.clone()
+            };
+
+            let new_job_id = Uuid::new_v4();
+            let now = chrono::Utc::now();
+
+            let record = crate::history::SandboxJobRecord {
+                id: new_job_id,
+                task: task.clone(),
+                status: "creating".to_string(),
+                user_id: old_job.user_id.clone(),
+                project_dir: old_job.project_dir.clone(),
+                success: None,
+                failure_reason: None,
+                created_at: now,
+                started_at: None,
+                completed_at: None,
+                credential_grants_json: old_job.credential_grants_json.clone(),
+            };
+            store
+                .save_sandbox_job(&record)
+                .await
+                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+            let mode = match store.get_sandbox_job_mode(old_job_id).await {
+                Ok(Some(m)) if m == "claude_code" => {
+                    crate::orchestrator::job_manager::JobMode::ClaudeCode
+                }
+                _ => crate::orchestrator::job_manager::JobMode::Worker,
+            };
+
+            let credential_grants: Vec<crate::orchestrator::auth::CredentialGrant> =
+                serde_json::from_str(&old_job.credential_grants_json).unwrap_or_else(|e| {
+                    tracing::warn!(
+                        job_id = %old_job.id,
+                        "Failed to deserialize credential grants from stored job: {}. \
+                         Restarted job will have no credentials.",
+                        e
+                    );
+                    vec![]
+                });
+
+            let project_dir = std::path::PathBuf::from(&old_job.project_dir);
+            let _token = jm
+                .create_job(
+                    new_job_id,
+                    &task,
+                    Some(project_dir),
+                    mode,
+                    credential_grants,
+                )
+                .await
+                .map_err(|e| {
+                    (
+                        StatusCode::INTERNAL_SERVER_ERROR,
+                        format!("Failed to create container: {}", e),
+                    )
+                })?;
+
+            store
+                .update_sandbox_job_status(new_job_id, "running", None, None, Some(now), None)
+                .await
+                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+            return Ok(Json(serde_json::json!({
+                "status": "restarted",
+                "old_job_id": old_job_id,
+                "new_job_id": new_job_id,
+            })));
+        }
+        Ok(None) => {}
+        Err(e) => {
             return Err((
-                StatusCode::CONFLICT,
-                format!("Cannot restart job in state '{}'", old_job.status),
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Database error: {}", e),
             ));
         }
-
-        let jm = state.job_manager.as_ref().ok_or((
-            StatusCode::SERVICE_UNAVAILABLE,
-            "Sandbox not enabled".to_string(),
-        ))?;
-
-        // Enrich the task with failure context.
-        let task = if let Some(ref reason) = old_job.failure_reason {
-            format!(
-                "Previous attempt failed: {}. Retry: {}",
-                reason, old_job.task
-            )
-        } else {
-            old_job.task.clone()
-        };
-
-        let new_job_id = Uuid::new_v4();
-        let now = chrono::Utc::now();
-
-        let record = crate::history::SandboxJobRecord {
-            id: new_job_id,
-            task: task.clone(),
-            status: "creating".to_string(),
-            user_id: old_job.user_id.clone(),
-            project_dir: old_job.project_dir.clone(),
-            success: None,
-            failure_reason: None,
-            created_at: now,
-            started_at: None,
-            completed_at: None,
-            credential_grants_json: old_job.credential_grants_json.clone(),
-        };
-        store
-            .save_sandbox_job(&record)
-            .await
-            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-
-        let mode = match store.get_sandbox_job_mode(old_job_id).await {
-            Ok(Some(m)) if m == "claude_code" => {
-                crate::orchestrator::job_manager::JobMode::ClaudeCode
-            }
-            _ => crate::orchestrator::job_manager::JobMode::Worker,
-        };
-
-        let credential_grants: Vec<crate::orchestrator::auth::CredentialGrant> =
-            serde_json::from_str(&old_job.credential_grants_json).unwrap_or_else(|e| {
-                tracing::warn!(
-                    job_id = %old_job.id,
-                    "Failed to deserialize credential grants from stored job: {}. \
-                     Restarted job will have no credentials.",
-                    e
-                );
-                vec![]
-            });
-
-        let project_dir = std::path::PathBuf::from(&old_job.project_dir);
-        let _token = jm
-            .create_job(
-                new_job_id,
-                &task,
-                Some(project_dir),
-                mode,
-                credential_grants,
-            )
-            .await
-            .map_err(|e| {
-                (
-                    StatusCode::INTERNAL_SERVER_ERROR,
-                    format!("Failed to create container: {}", e),
-                )
-            })?;
-
-        store
-            .update_sandbox_job_status(new_job_id, "running", None, None, Some(now), None)
-            .await
-            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-
-        return Ok(Json(serde_json::json!({
-            "status": "restarted",
-            "old_job_id": old_job_id,
-            "new_job_id": new_job_id,
-        })));
     }
 
     // Try agent job restart: dispatch a new job via the scheduler.
-    if let Ok(Some(old_job)) = store.get_job(old_job_id).await {
-        if old_job.state.is_active() {
-            return Err((
-                StatusCode::CONFLICT,
-                format!("Cannot restart job in state '{}'", old_job.state),
-            ));
+    match store.get_job(old_job_id).await {
+        Ok(Some(old_job)) => {
+            if old_job.user_id != user.user_id {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+            if old_job.state.is_active() {
+                return Err((
+                    StatusCode::CONFLICT,
+                    format!("Cannot restart job in state '{}'", old_job.state),
+                ));
+            }
+
+            let slot = state.scheduler.as_ref().ok_or((
+                StatusCode::SERVICE_UNAVAILABLE,
+                "Scheduler not available".to_string(),
+            ))?;
+            let scheduler_guard = slot.read().await;
+            let scheduler = scheduler_guard.as_ref().ok_or((
+                StatusCode::SERVICE_UNAVAILABLE,
+                "Agent not started yet".to_string(),
+            ))?;
+
+            // Look up failure reason (O(1) point lookup).
+            let failure_reason = store
+                .get_agent_job_failure_reason(old_job_id)
+                .await
+                .ok()
+                .flatten()
+                .unwrap_or_default();
+
+            let title = if !failure_reason.is_empty() {
+                format!(
+                    "Previous attempt failed: {}. Retry: {}",
+                    failure_reason, old_job.title
+                )
+            } else {
+                old_job.title.clone()
+            };
+
+            let new_job_id = scheduler
+                .dispatch_job(&old_job.user_id, &title, &old_job.description, None)
+                .await
+                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+            Ok(Json(serde_json::json!({
+                "status": "restarted",
+                "old_job_id": old_job_id,
+                "new_job_id": new_job_id,
+            })))
         }
-
-        let slot = state.scheduler.as_ref().ok_or((
-            StatusCode::SERVICE_UNAVAILABLE,
-            "Scheduler not available".to_string(),
-        ))?;
-        let scheduler_guard = slot.read().await;
-        let scheduler = scheduler_guard.as_ref().ok_or((
-            StatusCode::SERVICE_UNAVAILABLE,
-            "Agent not started yet".to_string(),
-        ))?;
-
-        // Look up failure reason (O(1) point lookup).
-        let failure_reason = store
-            .get_agent_job_failure_reason(old_job_id)
-            .await
-            .ok()
-            .flatten()
-            .unwrap_or_default();
-
-        let title = if !failure_reason.is_empty() {
-            format!(
-                "Previous attempt failed: {}. Retry: {}",
-                failure_reason, old_job.title
-            )
-        } else {
-            old_job.title.clone()
-        };
-
-        let new_job_id = scheduler
-            .dispatch_job(&old_job.user_id, &title, &old_job.description, None)
-            .await
-            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-
-        return Ok(Json(serde_json::json!({
-            "status": "restarted",
-            "old_job_id": old_job_id,
-            "new_job_id": new_job_id,
-        })));
+        Ok(None) => Err((StatusCode::NOT_FOUND, "Job not found".to_string())),
+        Err(e) => Err((
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Database error: {}", e),
+        )),
     }
-
-    Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
 }
 
 /// Submit a follow-up prompt to a running job.
@@ -476,6 +545,7 @@ pub async fn jobs_restart_handler(
 /// - Worker-mode sandbox jobs → not supported (no mechanism to inject)
 pub async fn jobs_prompt_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
     Json(body): Json<serde_json::Value>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
@@ -494,10 +564,15 @@ pub async fn jobs_prompt_handler(
 
     let done = body.get("done").and_then(|v| v.as_bool()).unwrap_or(false);
 
-    // Try sandbox job path: check if we have a sandbox record for this ID.
+    // Try sandbox job path first: verify ownership, then route to Claude Code or reject.
     if let Some(ref s) = state.store
-        && let Ok(Some(_)) = s.get_sandbox_job(job_id).await
+        && let Ok(Some(sandbox_job)) = s.get_sandbox_job(job_id).await
     {
+        // Verify ownership.
+        if sandbox_job.user_id != user.user_id {
+            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+        }
+
         // It's a sandbox job. Check if Claude Code mode.
         let mode = s.get_sandbox_job_mode(job_id).await.ok().flatten();
         if mode.as_deref() == Some("claude_code") {
@@ -522,7 +597,26 @@ pub async fn jobs_prompt_handler(
         }
     }
 
-    // Try agent job path: send via scheduler.
+    // Try agent job path: verify ownership, then send via scheduler.
+    if let Some(ref store) = state.store {
+        match store.get_job(job_id).await {
+            Ok(Some(agent_job)) => {
+                if agent_job.user_id != user.user_id {
+                    return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+                }
+            }
+            Ok(None) => {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+            Err(e) => {
+                return Err((
+                    StatusCode::INTERNAL_SERVER_ERROR,
+                    format!("Database error: {}", e),
+                ));
+            }
+        }
+    }
+
     let slot = state.scheduler.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Agent job prompts require the scheduler to be configured".to_string(),
@@ -550,6 +644,7 @@ pub async fn jobs_prompt_handler(
 /// Load persisted job events for a job (for history replay on page open).
 pub async fn jobs_events_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -561,6 +656,24 @@ pub async fn jobs_events_handler(
         .parse()
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
 
+    // Verify ownership before returning events.
+    match store.get_sandbox_job(job_id).await {
+        Ok(Some(job)) => {
+            if job.user_id != user.user_id {
+                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+            }
+        }
+        Ok(None) => {
+            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+        }
+        Err(e) => {
+            return Err((
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Database error: {}", e),
+            ));
+        }
+    }
+
     let events = store
         .list_job_events(job_id, None)
         .await
@@ -593,6 +706,7 @@ pub struct FilePathQuery {
 
 pub async fn job_files_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
     Query(query): Query<FilePathQuery>,
 ) -> Result<Json<ProjectFilesResponse>, (StatusCode, String)> {
@@ -610,6 +724,10 @@ pub async fn job_files_list_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
         .ok_or((StatusCode::NOT_FOUND, "Job not found".to_string()))?;
 
+    if job.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
     let base = std::path::PathBuf::from(&job.project_dir);
     let rel_path = query.path.as_deref().unwrap_or("");
     let target = base.join(rel_path);
@@ -656,6 +774,7 @@ pub async fn job_files_list_handler(
 
 pub async fn job_files_read_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
     Query(query): Query<FilePathQuery>,
 ) -> Result<Json<ProjectFileReadResponse>, (StatusCode, String)> {
@@ -673,6 +792,10 @@ pub async fn job_files_read_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
         .ok_or((StatusCode::NOT_FOUND, "Job not found".to_string()))?;
 
+    if job.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
     let path = query.path.as_deref().ok_or((
         StatusCode::BAD_REQUEST,
         "path parameter required".to_string(),

src/channels/web/handlers/memory.rs

@@ -9,8 +9,27 @@ use axum::{
 };
 use serde::Deserialize;
 
+use crate::channels::web::auth::{AuthenticatedUser, UserIdentity};
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
+use crate::workspace::Workspace;
+
+/// Resolve the workspace for the authenticated user.
+///
+/// Prefers `workspace_pool` (multi-user mode) when available, falling back
+/// to the single-user `state.workspace`.
+pub(crate) async fn resolve_workspace(
+    state: &GatewayState,
+    user: &UserIdentity,
+) -> Result<Arc<Workspace>, (StatusCode, String)> {
+    if let Some(ref pool) = state.workspace_pool {
+        return Ok(pool.get_or_create(user).await);
+    }
+    state.workspace.as_ref().cloned().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))
+}
 
 #[derive(Deserialize)]
 pub struct TreeQuery {
@@ -20,12 +39,10 @@ pub struct TreeQuery {
 
 pub async fn memory_tree_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Query(_query): Query<TreeQuery>,
 ) -> Result<Json<MemoryTreeResponse>, (StatusCode, String)> {
-    let workspace = state.workspace.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Workspace not available".to_string(),
-    ))?;
+    let workspace = resolve_workspace(&state, &user).await?;
 
     // Build tree from list_all (flat list of all paths)
     let all_paths = workspace
@@ -68,12 +85,10 @@ pub struct ListQuery {
 
 pub async fn memory_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Query(query): Query<ListQuery>,
 ) -> Result<Json<MemoryListResponse>, (StatusCode, String)> {
-    let workspace = state.workspace.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Workspace not available".to_string(),
-    ))?;
+    let workspace = resolve_workspace(&state, &user).await?;
 
     let path = query.path.as_deref().unwrap_or("");
     let entries = workspace
@@ -104,12 +119,10 @@ pub struct ReadQuery {
 
 pub async fn memory_read_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Query(query): Query<ReadQuery>,
 ) -> Result<Json<MemoryReadResponse>, (StatusCode, String)> {
-    let workspace = state.workspace.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Workspace not available".to_string(),
-    ))?;
+    let workspace = resolve_workspace(&state, &user).await?;
 
     let doc = workspace
         .read(&query.path)
@@ -123,17 +136,75 @@ pub async fn memory_read_handler(
     }))
 }
 
-// memory_write_handler lives in server.rs (layer-aware version with append,
-// privacy redirect, and proper error status codes).
+pub async fn memory_write_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+    Json(req): Json<MemoryWriteRequest>,
+) -> Result<Json<MemoryWriteResponse>, (StatusCode, String)> {
+    let workspace = resolve_workspace(&state, &user).await?;
+
+    // Route through layer-aware methods when a layer is specified.
+    //
+    // Note: unlike MemoryWriteTool, this endpoint does NOT block writes to
+    // identity files (IDENTITY.md, SOUL.md, etc.). The HTTP API is an
+    // authenticated admin interface; the supervisor uses it to seed identity
+    // files at startup. Identity-file protection is enforced at the tool
+    // layer (LLM-facing) where the write originates from an untrusted agent.
+    if let Some(ref layer_name) = req.layer {
+        let result = if req.append {
+            workspace
+                .append_to_layer(layer_name, &req.path, &req.content, req.force)
+                .await
+        } else {
+            workspace
+                .write_to_layer(layer_name, &req.path, &req.content, req.force)
+                .await
+        }
+        .map_err(|e| {
+            use crate::error::WorkspaceError;
+            let status = match &e {
+                WorkspaceError::LayerNotFound { .. } => StatusCode::BAD_REQUEST,
+                WorkspaceError::LayerReadOnly { .. } => StatusCode::FORBIDDEN,
+                WorkspaceError::PrivacyRedirectFailed => StatusCode::UNPROCESSABLE_ENTITY,
+                _ => StatusCode::INTERNAL_SERVER_ERROR,
+            };
+            (status, e.to_string())
+        })?;
+        return Ok(Json(MemoryWriteResponse {
+            path: req.path,
+            status: "written",
+            redirected: Some(result.redirected),
+            actual_layer: Some(result.actual_layer),
+        }));
+    }
+
+    // Non-layer path: honor the append field
+    if req.append {
+        workspace
+            .append(&req.path, &req.content)
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+    } else {
+        workspace
+            .write(&req.path, &req.content)
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+    }
+
+    Ok(Json(MemoryWriteResponse {
+        path: req.path,
+        status: "written",
+        redirected: None,
+        actual_layer: None,
+    }))
+}
 
 pub async fn memory_search_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Json(req): Json<MemorySearchRequest>,
 ) -> Result<Json<MemorySearchResponse>, (StatusCode, String)> {
-    let workspace = state.workspace.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Workspace not available".to_string(),
-    ))?;
+    let workspace = resolve_workspace(&state, &user).await?;
 
     let limit = req.limit.unwrap_or(10);
     let results = workspace
@@ -142,10 +213,10 @@ pub async fn memory_search_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
     let hits: Vec<SearchHit> = results
-        .into_iter()
+        .iter()
         .map(|r| SearchHit {
-            path: r.document_path,
-            content: r.content,
+            path: r.document_id.to_string(),
+            content: r.content.clone(),
             score: r.score as f64,
         })
         .collect();

src/channels/web/handlers/mod.rs

@@ -1,13 +1,10 @@
 //! Handler modules for the web gateway API.
 //!
 //! Each module groups related endpoint handlers by domain.
-//!
-//! # Migration status
-//!
-//! `skills` is the canonical implementation used by `server.rs`.
-//! The remaining modules are in-progress migrations from inline server.rs
-//! handlers; their functions are not yet wired up, hence the `dead_code` allow.
 
+pub mod jobs;
+pub mod memory;
+pub mod routines;
 pub mod skills;
 
 // Modules not yet wired into server.rs router -- suppress dead_code until
@@ -17,12 +14,6 @@ pub mod chat;
 #[allow(dead_code)]
 pub mod extensions;
 #[allow(dead_code)]
-pub mod jobs;
-#[allow(dead_code)]
-pub mod memory;
-#[allow(dead_code)]
-pub mod routines;
-#[allow(dead_code)]
 pub mod settings;
 #[allow(dead_code)]
 pub mod static_files;

src/channels/web/handlers/routines.rs

@@ -11,12 +11,14 @@ use serde::Deserialize;
 use uuid::Uuid;
 
 use crate::agent::routine::{Trigger, next_cron_fire};
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 use crate::error::RoutineError;
 
 pub async fn routines_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<RoutineListResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
@@ -24,7 +26,7 @@ pub async fn routines_list_handler(
     ))?;
 
     let routines = store
-        .list_all_routines()
+        .list_routines(&user.user_id)
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
@@ -35,6 +37,7 @@ pub async fn routines_list_handler(
 
 pub async fn routines_summary_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<RoutineSummaryResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
@@ -42,7 +45,7 @@ pub async fn routines_summary_handler(
     ))?;
 
     let routines = store
-        .list_all_routines()
+        .list_routines(&user.user_id)
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
@@ -78,6 +81,7 @@ pub async fn routines_summary_handler(
 
 pub async fn routines_detail_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<RoutineDetailResponse>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -94,6 +98,10 @@ pub async fn routines_detail_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
         .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
 
+    if routine.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Routine not found".to_string()));
+    }
+
     let runs = store
         .list_routine_runs(routine_id, 20)
         .await
@@ -106,7 +114,7 @@ pub async fn routines_detail_handler(
             trigger_type: run.trigger_type.clone(),
             started_at: run.started_at.to_rfc3339(),
             completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
-            status: format!("{:?}", run.status),
+            status: run.status.to_string(),
             result_summary: run.result_summary.clone(),
             tokens_used: run.tokens_used,
             job_id: run.job_id,
@@ -137,6 +145,7 @@ pub async fn routines_detail_handler(
 
 pub async fn routines_trigger_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     // Clone the Arc out of the lock to avoid holding the RwLock across .await.
@@ -152,7 +161,7 @@ pub async fn routines_trigger_handler(
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
 
     let run_id = engine
-        .fire_manual(routine_id, Some(&state.user_id))
+        .fire_manual(routine_id, Some(&user.user_id))
         .await
         .map_err(|e| (routine_error_status(&e), e.to_string()))?;
 
@@ -170,6 +179,7 @@ pub struct ToggleRequest {
 
 pub async fn routines_toggle_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
     body: Option<Json<ToggleRequest>>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
@@ -187,6 +197,10 @@ pub async fn routines_toggle_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
         .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
 
+    if routine.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Routine not found".to_string()));
+    }
+
     let was_enabled = routine.enabled;
     // If a specific value was provided, use it; otherwise toggle.
     routine.enabled = match body {
@@ -230,6 +244,7 @@ pub async fn routines_toggle_handler(
 
 pub async fn routines_delete_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -240,6 +255,17 @@ pub async fn routines_delete_handler(
     let routine_id = Uuid::parse_str(&id)
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
 
+    // Verify ownership before deleting.
+    let routine = store
+        .get_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
+
+    if routine.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Routine not found".to_string()));
+    }
+
     let deleted = store
         .delete_routine(routine_id)
         .await
@@ -261,8 +287,10 @@ pub async fn routines_delete_handler(
     }
 }
 
+#[allow(dead_code)] // Used by server.rs inline version; kept in sync here for future migration.
 pub async fn routines_runs_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(id): Path<String>,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
     let store = state.store.as_ref().ok_or((
@@ -273,6 +301,17 @@ pub async fn routines_runs_handler(
     let routine_id = Uuid::parse_str(&id)
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
 
+    // Verify ownership before listing runs.
+    let routine = store
+        .get_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
+
+    if routine.user_id != user.user_id {
+        return Err((StatusCode::NOT_FOUND, "Routine not found".to_string()));
+    }
+
     let runs = store
         .list_routine_runs(routine_id, 50)
         .await
@@ -285,7 +324,7 @@ pub async fn routines_runs_handler(
             trigger_type: run.trigger_type.clone(),
             started_at: run.started_at.to_rfc3339(),
             completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
-            status: format!("{:?}", run.status),
+            status: run.status.to_string(),
             result_summary: run.result_summary.clone(),
             tokens_used: run.tokens_used,
             job_id: run.job_id,

src/channels/web/handlers/settings.rs

@@ -8,17 +8,19 @@ use axum::{
     http::StatusCode,
 };
 
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 
 pub async fn settings_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<SettingsListResponse>, StatusCode> {
     let store = state
         .store
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
-    let rows = store.list_settings(&state.user_id).await.map_err(|e| {
+    let rows = store.list_settings(&user.user_id).await.map_err(|e| {
         tracing::error!("Failed to list settings: {}", e);
         StatusCode::INTERNAL_SERVER_ERROR
     })?;
@@ -37,6 +39,7 @@ pub async fn settings_list_handler(
 
 pub async fn settings_get_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(key): Path<String>,
 ) -> Result<Json<SettingResponse>, StatusCode> {
     let store = state
@@ -44,7 +47,7 @@ pub async fn settings_get_handler(
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
     let row = store
-        .get_setting_full(&state.user_id, &key)
+        .get_setting_full(&user.user_id, &key)
         .await
         .map_err(|e| {
             tracing::error!("Failed to get setting '{}': {}", key, e);
@@ -61,6 +64,7 @@ pub async fn settings_get_handler(
 
 pub async fn settings_set_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(key): Path<String>,
     Json(body): Json<SettingWriteRequest>,
 ) -> Result<StatusCode, StatusCode> {
@@ -69,7 +73,7 @@ pub async fn settings_set_handler(
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
     store
-        .set_setting(&state.user_id, &key, &body.value)
+        .set_setting(&user.user_id, &key, &body.value)
         .await
         .map_err(|e| {
             tracing::error!("Failed to set setting '{}': {}", key, e);
@@ -81,6 +85,7 @@ pub async fn settings_set_handler(
 
 pub async fn settings_delete_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Path(key): Path<String>,
 ) -> Result<StatusCode, StatusCode> {
     let store = state
@@ -88,7 +93,7 @@ pub async fn settings_delete_handler(
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
     store
-        .delete_setting(&state.user_id, &key)
+        .delete_setting(&user.user_id, &key)
         .await
         .map_err(|e| {
             tracing::error!("Failed to delete setting '{}': {}", key, e);
@@ -100,12 +105,13 @@ pub async fn settings_delete_handler(
 
 pub async fn settings_export_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
 ) -> Result<Json<SettingsExportResponse>, StatusCode> {
     let store = state
         .store
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
-    let settings = store.get_all_settings(&state.user_id).await.map_err(|e| {
+    let settings = store.get_all_settings(&user.user_id).await.map_err(|e| {
         tracing::error!("Failed to export settings: {}", e);
         StatusCode::INTERNAL_SERVER_ERROR
     })?;
@@ -115,6 +121,7 @@ pub async fn settings_export_handler(
 
 pub async fn settings_import_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     Json(body): Json<SettingsImportRequest>,
 ) -> Result<StatusCode, StatusCode> {
     let store = state
@@ -122,7 +129,7 @@ pub async fn settings_import_handler(
         .as_ref()
         .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
     store
-        .set_all_settings(&state.user_id, &body.settings)
+        .set_all_settings(&user.user_id, &body.settings)
         .await
         .map_err(|e| {
             tracing::error!("Failed to import settings: {}", e);

src/channels/web/handlers/skills.rs

@@ -8,11 +8,13 @@ use axum::{
     http::StatusCode,
 };
 
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
 
 pub async fn skills_list_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(_user): AuthenticatedUser,
 ) -> Result<Json<SkillListResponse>, (StatusCode, String)> {
     let registry = state.skill_registry.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
@@ -45,6 +47,7 @@ pub async fn skills_list_handler(
 
 pub async fn skills_search_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(_user): AuthenticatedUser,
     Json(req): Json<SkillSearchRequest>,
 ) -> Result<Json<SkillSearchResponse>, (StatusCode, String)> {
     let registry = state.skill_registry.as_ref().ok_or((
@@ -119,6 +122,7 @@ pub async fn skills_search_handler(
 
 pub async fn skills_install_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     headers: axum::http::HeaderMap,
     Json(req): Json<SkillInstallRequest>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
@@ -135,6 +139,8 @@ pub async fn skills_install_handler(
         ));
     }
 
+    tracing::info!(user_id = %user.user_id, skill = %req.name, "skill install requested");
+
     let registry = state.skill_registry.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Skills system not enabled".to_string(),
@@ -219,6 +225,7 @@ pub async fn skills_install_handler(
 
 pub async fn skills_remove_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
     headers: axum::http::HeaderMap,
     Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
@@ -234,6 +241,8 @@ pub async fn skills_remove_handler(
         ));
     }
 
+    tracing::info!(user_id = %user.user_id, skill = %name, "skill remove requested");
+
     let registry = state.skill_registry.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Skills system not enabled".to_string(),

src/channels/web/handlers/static_files.rs

@@ -7,6 +7,7 @@ use axum::{
 };
 
 use crate::bootstrap::ironclaw_base_dir;
+use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::types::*;
 
 // --- Static file handlers ---
@@ -113,6 +114,7 @@ use crate::channels::web::server::GatewayState;
 
 pub async fn logs_events_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(_user): AuthenticatedUser,
 ) -> Result<
     Sse<impl futures::Stream<Item = Result<Event, Infallible>> + Send + 'static>,
     (StatusCode, String),
@@ -152,6 +154,7 @@ pub async fn logs_events_handler(
 
 pub async fn gateway_status_handler(
     State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(_user): AuthenticatedUser,
 ) -> Json<GatewayStatusResponse> {
     let sse_connections = state.sse.connection_count();
     let ws_connections = state

src/channels/web/mod.rs

@@ -31,6 +31,9 @@ pub mod ws;
 /// [`TestGatewayBuilder`](test_helpers::TestGatewayBuilder).
 pub mod test_helpers;
 
+#[cfg(test)]
+mod tests;
+
 use std::net::SocketAddr;
 use std::sync::Arc;
 
@@ -52,6 +55,7 @@ use crate::workspace::Workspace;
 
 use self::log_layer::{LogBroadcaster, LogLevelHandle};
 
+use self::auth::MultiAuthState;
 use self::server::GatewayState;
 use self::sse::SseManager;
 use self::types::SseEvent;
@@ -60,14 +64,15 @@ use self::types::SseEvent;
 pub struct GatewayChannel {
     config: GatewayConfig,
     state: Arc<GatewayState>,
-    /// The actual auth token in use (generated or from config).
-    auth_token: String,
+    /// Multi-user auth state (replaces bare auth_token).
+    auth: MultiAuthState,
 }
 
 impl GatewayChannel {
     /// Create a new gateway channel.
     ///
     /// If no auth token is configured, generates a random one and prints it.
+    /// Builds a single-user `MultiAuthState` from the config.
     pub fn new(config: GatewayConfig) -> Self {
         let auth_token = config.auth_token.clone().unwrap_or_else(|| {
             use rand::RngCore;
@@ -77,10 +82,13 @@ impl GatewayChannel {
             bytes.iter().map(|b| format!("{b:02x}")).collect()
         });
 
+        let auth = MultiAuthState::single(auth_token, config.user_id.clone());
+
         let state = Arc::new(GatewayState {
             msg_tx: tokio::sync::RwLock::new(None),
-            sse: SseManager::new(),
+            sse: Arc::new(SseManager::new()),
             workspace: None,
+            workspace_pool: None,
             session_manager: None,
             log_broadcaster: None,
             log_level_handle: None,
@@ -90,13 +98,14 @@ impl GatewayChannel {
             job_manager: None,
             prompt_queue: None,
             scheduler: None,
-            user_id: config.user_id.clone(),
+            owner_id: config.user_id.clone(),
+            default_sender_id: config.user_id.clone(),
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(ws::WsConnectionTracker::new())),
             llm_provider: None,
             skill_registry: None,
             skill_catalog: None,
-            chat_rate_limiter: server::RateLimiter::new(30, 60),
+            chat_rate_limiter: server::PerUserRateLimiter::new(30, 60),
             oauth_rate_limiter: server::RateLimiter::new(10, 60),
             webhook_rate_limiter: server::RateLimiter::new(10, 60),
             registry_entries: Vec::new(),
@@ -109,7 +118,63 @@ impl GatewayChannel {
         Self {
             config,
             state,
-            auth_token,
+            auth,
+        }
+    }
+
+    /// Rebind the single-user auth identity to the durable owner scope while
+    /// preserving the configured gateway sender/routing identity.
+    pub fn with_owner_scope(mut self, owner_id: impl Into<String>) -> Self {
+        let owner_id = owner_id.into();
+        let single_user_token = if self.config.user_tokens.is_none() {
+            self.auth.first_token().map(ToOwned::to_owned)
+        } else {
+            None
+        };
+        if let Some(token) = single_user_token {
+            self.auth = MultiAuthState::single(token, owner_id.clone());
+        }
+        self.rebuild_state(|s| s.owner_id = owner_id);
+        self
+    }
+
+    /// Create a gateway channel with a pre-built multi-user auth state.
+    pub fn new_multi_auth(config: GatewayConfig, auth: MultiAuthState) -> Self {
+        let state = Arc::new(GatewayState {
+            msg_tx: tokio::sync::RwLock::new(None),
+            sse: Arc::new(SseManager::new()),
+            workspace: None,
+            workspace_pool: None,
+            session_manager: None,
+            log_broadcaster: None,
+            log_level_handle: None,
+            extension_manager: None,
+            tool_registry: None,
+            store: None,
+            job_manager: None,
+            prompt_queue: None,
+            scheduler: None,
+            owner_id: config.user_id.clone(),
+            default_sender_id: config.user_id.clone(),
+            shutdown_tx: tokio::sync::RwLock::new(None),
+            ws_tracker: Some(Arc::new(ws::WsConnectionTracker::new())),
+            llm_provider: None,
+            skill_registry: None,
+            skill_catalog: None,
+            chat_rate_limiter: server::PerUserRateLimiter::new(30, 60),
+            oauth_rate_limiter: server::RateLimiter::new(10, 60),
+            registry_entries: Vec::new(),
+            cost_guard: None,
+            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
+            startup_time: std::time::Instant::now(),
+            webhook_rate_limiter: server::RateLimiter::new(10, 60),
+            active_config: server::ActiveConfigSnapshot::default(),
+        });
+
+        Self {
+            config,
+            state,
+            auth,
         }
     }
 
@@ -118,8 +183,9 @@ impl GatewayChannel {
         let mut new_state = GatewayState {
             msg_tx: tokio::sync::RwLock::new(None),
             // Preserve the existing broadcast channel so sender handles remain valid.
-            sse: SseManager::from_sender(self.state.sse.sender()),
+            sse: Arc::new(SseManager::from_sender(self.state.sse.sender())),
             workspace: self.state.workspace.clone(),
+            workspace_pool: self.state.workspace_pool.clone(),
             session_manager: self.state.session_manager.clone(),
             log_broadcaster: self.state.log_broadcaster.clone(),
             log_level_handle: self.state.log_level_handle.clone(),
@@ -129,13 +195,14 @@ impl GatewayChannel {
             job_manager: self.state.job_manager.clone(),
             prompt_queue: self.state.prompt_queue.clone(),
             scheduler: self.state.scheduler.clone(),
-            user_id: self.state.user_id.clone(),
+            owner_id: self.state.owner_id.clone(),
+            default_sender_id: self.state.default_sender_id.clone(),
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: self.state.ws_tracker.clone(),
             llm_provider: self.state.llm_provider.clone(),
             skill_registry: self.state.skill_registry.clone(),
             skill_catalog: self.state.skill_catalog.clone(),
-            chat_rate_limiter: server::RateLimiter::new(30, 60),
+            chat_rate_limiter: server::PerUserRateLimiter::new(30, 60),
             oauth_rate_limiter: server::RateLimiter::new(10, 60),
             webhook_rate_limiter: server::RateLimiter::new(10, 60),
             registry_entries: self.state.registry_entries.clone(),
@@ -260,9 +327,15 @@ impl GatewayChannel {
         self
     }
 
-    /// Get the auth token (for printing to console on startup).
+    /// Inject the per-user workspace pool for multi-user mode.
+    pub fn with_workspace_pool(mut self, pool: Arc<server::WorkspacePool>) -> Self {
+        self.rebuild_state(|s| s.workspace_pool = Some(pool));
+        self
+    }
+
+    /// Get the first auth token (for printing to console on startup).
     pub fn auth_token(&self) -> &str {
-        &self.auth_token
+        self.auth.first_token().unwrap_or("")
     }
 
     /// Get a reference to the shared gateway state (for the agent to push SSE events).
@@ -291,7 +364,7 @@ impl Channel for GatewayChannel {
                 ),
             })?;
 
-        server::start_server(addr, self.state.clone(), self.auth_token.clone()).await?;
+        server::start_server(addr, self.state.clone(), self.auth.clone()).await?;
 
         Ok(Box::pin(ReceiverStream::new(rx)))
     }
@@ -311,10 +384,13 @@ impl Channel for GatewayChannel {
             }
         };
 
-        self.state.sse.broadcast(SseEvent::Response {
-            content: response.content,
-            thread_id,
-        });
+        self.state.sse.broadcast_for_user(
+            &msg.user_id,
+            SseEvent::Response {
+                content: response.content,
+                thread_id,
+            },
+        );
 
         Ok(())
     }
@@ -427,13 +503,21 @@ impl Channel for GatewayChannel {
             },
         };
 
-        self.state.sse.broadcast(event);
+        // Scope events to the user when user_id is available in metadata.
+        // When user_id is missing (heartbeat, routines), events go to all
+        // subscribers. In multi-tenant mode this leaks status across users.
+        if let Some(uid) = metadata.get("user_id").and_then(|v| v.as_str()) {
+            self.state.sse.broadcast_for_user(uid, event);
+        } else {
+            tracing::debug!("Status event missing user_id in metadata; broadcasting globally");
+            self.state.sse.broadcast(event);
+        }
         Ok(())
     }
 
     async fn broadcast(
         &self,
-        _user_id: &str,
+        user_id: &str,
         response: OutgoingResponse,
     ) -> Result<(), ChannelError> {
         let thread_id = match response.thread_id {
@@ -445,10 +529,13 @@ impl Channel for GatewayChannel {
                 return Ok(());
             }
         };
-        self.state.sse.broadcast(SseEvent::Response {
-            content: response.content,
-            thread_id,
-        });
+        self.state.sse.broadcast_for_user(
+            user_id,
+            SseEvent::Response {
+                content: response.content,
+                thread_id,
+            },
+        );
         Ok(())
     }
 

src/channels/web/openai_compat.rs

@@ -463,9 +463,10 @@ fn build_tool_request(
 
 pub async fn chat_completions_handler(
     State(state): State<Arc<GatewayState>>,
+    super::auth::AuthenticatedUser(user): super::auth::AuthenticatedUser,
     Json(req): Json<OpenAiChatRequest>,
 ) -> Result<impl IntoResponse, (StatusCode, Json<OpenAiErrorResponse>)> {
-    if !state.chat_rate_limiter.check() {
+    if !state.chat_rate_limiter.check(&user.user_id) {
         return Err(openai_error(
             StatusCode::TOO_MANY_REQUESTS,
             "Rate limit exceeded. Please try again later.",

src/channels/web/sse.rs

@@ -17,9 +17,25 @@ use crate::channels::web::types::SseEvent;
 /// Prevents resource exhaustion from connection flooding.
 const MAX_CONNECTIONS: u64 = 100;
 
+/// Envelope for broadcast events: carries an optional user scope.
+///
+/// `user_id = None` means the event is global (e.g. Heartbeat) and delivered
+/// to all subscribers. `user_id = Some(id)` means the event is only delivered
+/// to subscribers that match that user_id.
+#[derive(Debug, Clone)]
+pub(crate) struct ScopedEvent {
+    pub(crate) user_id: Option<String>,
+    pub(crate) event: SseEvent,
+}
+
 /// Manages SSE broadcast to all connected browser tabs.
+///
+/// In multi-user mode, events are scoped by user_id so that each subscriber
+/// only receives events intended for their user (plus global events like
+/// Heartbeat). In single-user mode, all events are delivered to all subscribers
+/// (backwards compatible).
 pub struct SseManager {
-    tx: broadcast::Sender<SseEvent>,
+    tx: broadcast::Sender<ScopedEvent>,
     connection_count: Arc<AtomicU64>,
     max_connections: u64,
 }
@@ -45,7 +61,7 @@ impl SseManager {
     /// only be called before the server starts accepting connections (i.e.,
     /// during startup wiring). Calling it after connections are established
     /// will break connection tracking and allow exceeding `MAX_CONNECTIONS`.
-    pub fn from_sender(tx: broadcast::Sender<SseEvent>) -> Self {
+    pub(crate) fn from_sender(tx: broadcast::Sender<ScopedEvent>) -> Self {
         Self {
             tx,
             connection_count: Arc::new(AtomicU64::new(0)),
@@ -53,15 +69,28 @@ impl SseManager {
         }
     }
 
-    /// Broadcast an event to all connected clients.
-    pub fn broadcast(&self, event: SseEvent) {
-        // Ignore send errors (no receivers is fine)
-        let _ = self.tx.send(event);
+    /// Get a clone of the broadcast sender for use by other components.
+    pub(crate) fn sender(&self) -> broadcast::Sender<ScopedEvent> {
+        self.tx.clone()
     }
 
-    /// Get a clone of the broadcast sender for use by other components.
-    pub fn sender(&self) -> broadcast::Sender<SseEvent> {
-        self.tx.clone()
+    /// Broadcast an event to all connected clients (global/unscoped).
+    pub fn broadcast(&self, event: SseEvent) {
+        let _ = self.tx.send(ScopedEvent {
+            user_id: None,
+            event,
+        });
+    }
+
+    /// Broadcast an event scoped to a specific user.
+    ///
+    /// Only subscribers for this user_id (or unscoped subscribers) will
+    /// receive the event.
+    pub fn broadcast_for_user(&self, user_id: &str, event: SseEvent) {
+        let _ = self.tx.send(ScopedEvent {
+            user_id: Some(user_id.to_string()),
+            event,
+        });
     }
 
     /// Get current number of active connections.
@@ -71,11 +100,15 @@ impl SseManager {
 
     /// Create a raw broadcast subscription for non-SSE consumers (e.g. WebSocket).
     ///
-    /// Returns a stream of `SseEvent` values and increments/decrements the
-    /// connection counter on creation/drop, just like `subscribe()` does for SSE.
+    /// When `user_id` is `Some`, only events scoped to that user (or global
+    /// events) are delivered. When `None`, all events are delivered (single-user
+    /// backwards compatibility).
     ///
     /// Returns `None` if the maximum connection limit has been reached.
-    pub fn subscribe_raw(&self) -> Option<impl Stream<Item = SseEvent> + Send + 'static + use<>> {
+    pub fn subscribe_raw(
+        &self,
+        user_id: Option<String>,
+    ) -> Option<impl Stream<Item = SseEvent> + Send + 'static + use<>> {
         // Atomically increment only if below the limit. This prevents
         // concurrent callers from overshooting max_connections.
         let counter = Arc::clone(&self.connection_count);
@@ -91,7 +124,19 @@ impl SseManager {
             .ok()?;
         let rx = self.tx.subscribe();
 
-        let stream = BroadcastStream::new(rx).filter_map(|result| result.ok());
+        let stream = BroadcastStream::new(rx).filter_map(move |result| match result {
+            Ok(scoped) => {
+                // Global events (user_id=None) always pass through.
+                // Scoped events only pass if the subscriber matches (or subscriber is unscoped).
+                match (&user_id, &scoped.user_id) {
+                    (_, None) => Some(scoped.event), // global -> all
+                    (None, _) => Some(scoped.event), // unscoped subscriber -> all
+                    (Some(sub), Some(ev)) if sub == ev => Some(scoped.event), // match
+                    _ => None,                       // different user -> skip
+                }
+            }
+            Err(_) => None,
+        });
 
         Some(CountedStream {
             inner: stream,
@@ -101,9 +146,13 @@ impl SseManager {
 
     /// Create a new SSE stream for a client connection.
     ///
+    /// When `user_id` is `Some`, only events for that user (or global events)
+    /// are delivered. When `None`, all events are delivered.
+    ///
     /// Returns `None` if the maximum connection limit has been reached.
     pub fn subscribe(
         &self,
+        user_id: Option<String>,
     ) -> Option<Sse<impl Stream<Item = Result<Event, Infallible>> + Send + 'static + use<>>> {
         // Atomically increment only if below the limit.
         let counter = Arc::clone(&self.connection_count);
@@ -120,9 +169,23 @@ impl SseManager {
         let rx = self.tx.subscribe();
 
         let stream = BroadcastStream::new(rx)
-            .filter_map(|result| result.ok())
-            .map(|event| {
-                let data = serde_json::to_string(&event).unwrap_or_default();
+            .filter_map(move |result| match result {
+                Ok(scoped) => match (&user_id, &scoped.user_id) {
+                    (_, None) => Some(scoped.event),
+                    (None, _) => Some(scoped.event),
+                    (Some(sub), Some(ev)) if sub == ev => Some(scoped.event),
+                    _ => None,
+                },
+                Err(_) => None,
+            })
+            .filter_map(|event| {
+                let data = match serde_json::to_string(&event) {
+                    Ok(s) => s,
+                    Err(e) => {
+                        tracing::warn!("Failed to serialize SSE event: {}", e);
+                        return None;
+                    }
+                };
                 let event_type = match &event {
                     SseEvent::Response { .. } => "response",
                     SseEvent::Thinking { .. } => "thinking",
@@ -147,7 +210,7 @@ impl SseManager {
                     SseEvent::TurnCost { .. } => "turn_cost",
                     SseEvent::ExtensionStatus { .. } => "extension_status",
                 };
-                Ok(Event::default().event(event_type).data(data))
+                Some(Ok(Event::default().event(event_type).data(data)))
             });
 
         // Wrap in a stream that decrements on drop
@@ -215,16 +278,14 @@ mod tests {
     #[tokio::test]
     async fn test_broadcast_to_receiver() {
         let manager = SseManager::new();
-        let mut rx = BroadcastStream::new(manager.tx.subscribe());
+        let mut stream = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
 
         manager.broadcast(SseEvent::Status {
             message: "test".to_string(),
             thread_id: None,
         });
 
-        let event = rx.next().await;
-        assert!(event.is_some());
-        let event = event.unwrap().unwrap();
+        let event = stream.next().await.unwrap();
         match event {
             SseEvent::Status { message, .. } => assert_eq!(message, "test"),
             _ => panic!("unexpected event type"),
@@ -234,7 +295,7 @@ mod tests {
     #[tokio::test]
     async fn test_subscribe_raw_receives_events() {
         let manager = SseManager::new();
-        let mut stream = Box::pin(manager.subscribe_raw().expect("should subscribe"));
+        let mut stream = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
 
         assert_eq!(manager.connection_count(), 1);
 
@@ -254,7 +315,7 @@ mod tests {
     async fn test_subscribe_raw_decrements_on_drop() {
         let manager = SseManager::new();
         {
-            let _stream = Box::pin(manager.subscribe_raw().expect("should subscribe"));
+            let _stream = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
             assert_eq!(manager.connection_count(), 1);
         }
         // Stream dropped, counter should decrement
@@ -264,8 +325,8 @@ mod tests {
     #[tokio::test]
     async fn test_subscribe_raw_multiple_subscribers() {
         let manager = SseManager::new();
-        let mut s1 = Box::pin(manager.subscribe_raw().expect("should subscribe"));
-        let mut s2 = Box::pin(manager.subscribe_raw().expect("should subscribe"));
+        let mut s1 = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
+        let mut s2 = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
         assert_eq!(manager.connection_count(), 2);
 
         manager.broadcast(SseEvent::Heartbeat);
@@ -286,12 +347,51 @@ mod tests {
         let mut manager = SseManager::new();
         manager.max_connections = 2; // Low limit for testing
 
-        let _s1 = Box::pin(manager.subscribe_raw().expect("first should succeed"));
-        let _s2 = Box::pin(manager.subscribe_raw().expect("second should succeed"));
+        let _s1 = Box::pin(manager.subscribe_raw(None).expect("first should succeed"));
+        let _s2 = Box::pin(manager.subscribe_raw(None).expect("second should succeed"));
         assert_eq!(manager.connection_count(), 2);
 
         // Third should be rejected
-        assert!(manager.subscribe_raw().is_none());
-        assert!(manager.subscribe().is_none());
+        assert!(manager.subscribe_raw(None).is_none());
+        assert!(manager.subscribe(None).is_none());
+    }
+
+    #[tokio::test]
+    async fn test_scoped_events_filtered_by_user() {
+        let manager = SseManager::new();
+        let mut alice = Box::pin(
+            manager
+                .subscribe_raw(Some("alice".to_string()))
+                .expect("subscribe"),
+        );
+        let mut bob = Box::pin(
+            manager
+                .subscribe_raw(Some("bob".to_string()))
+                .expect("subscribe"),
+        );
+
+        // Send event scoped to alice
+        manager.broadcast_for_user(
+            "alice",
+            SseEvent::Status {
+                message: "alice only".to_string(),
+                thread_id: None,
+            },
+        );
+
+        // Send global event
+        manager.broadcast(SseEvent::Heartbeat);
+
+        // Alice gets her scoped event
+        let e = alice.next().await.unwrap();
+        assert!(matches!(e, SseEvent::Status { .. }));
+
+        // Alice also gets the global heartbeat
+        let e = alice.next().await.unwrap();
+        assert!(matches!(e, SseEvent::Heartbeat));
+
+        // Bob only gets the global heartbeat (alice's event was filtered)
+        let e = bob.next().await.unwrap(); // safety: test-only
+        assert!(matches!(e, SseEvent::Heartbeat)); // safety: test assertion
     }
 }

src/channels/web/static/app.js

@@ -4265,9 +4265,9 @@ function renderRoutineDetail(routine) {
       + '<th>Trigger</th><th>Started</th><th>Completed</th><th>Status</th><th>Summary</th><th>Tokens</th>'
       + '</tr></thead><tbody>';
     for (const run of routine.recent_runs) {
-      const runStatusClass = run.status === 'Ok' ? 'completed'
-        : run.status === 'Failed' ? 'failed'
-        : run.status === 'Attention' ? 'stuck'
+      const runStatusClass = run.status === 'ok' ? 'completed'
+        : run.status === 'failed' ? 'failed'
+        : run.status === 'attention' ? 'stuck'
         : 'in_progress';
       html += '<tr>'
         + '<td>' + escapeHtml(run.trigger_type) + '</td>'

src/channels/web/test_helpers.rs

@@ -10,7 +10,8 @@ use std::sync::Arc;
 use tokio::sync::mpsc;
 
 use crate::channels::IncomingMessage;
-use crate::channels::web::server::{GatewayState, RateLimiter, start_server};
+use crate::channels::web::auth::MultiAuthState;
+use crate::channels::web::server::{GatewayState, PerUserRateLimiter, RateLimiter, start_server};
 use crate::channels::web::sse::SseManager;
 use crate::channels::web::ws::WsConnectionTracker;
 
@@ -64,8 +65,9 @@ impl TestGatewayBuilder {
     pub fn build(self) -> Arc<GatewayState> {
         Arc::new(GatewayState {
             msg_tx: tokio::sync::RwLock::new(self.msg_tx),
-            sse: SseManager::new(),
+            sse: Arc::new(SseManager::new()),
             workspace: None,
+            workspace_pool: None,
             session_manager: None,
             log_broadcaster: None,
             log_level_handle: None,
@@ -74,14 +76,15 @@ impl TestGatewayBuilder {
             store: None,
             job_manager: None,
             prompt_queue: None,
-            user_id: self.user_id,
+            owner_id: self.user_id.clone(),
+            default_sender_id: self.user_id,
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
             llm_provider: self.llm_provider,
             skill_registry: None,
             skill_catalog: None,
             scheduler: None,
-            chat_rate_limiter: RateLimiter::new(30, 60),
+            chat_rate_limiter: PerUserRateLimiter::new(30, 60),
             oauth_rate_limiter: RateLimiter::new(10, 60),
             webhook_rate_limiter: RateLimiter::new(10, 60),
             registry_entries: Vec::new(),
@@ -98,11 +101,26 @@ impl TestGatewayBuilder {
         self,
         auth_token: &str,
     ) -> Result<(SocketAddr, Arc<GatewayState>), crate::error::ChannelError> {
+        let auth = MultiAuthState::single(auth_token.to_string(), "test-user".to_string());
         let state = self.build();
         let addr: SocketAddr = "127.0.0.1:0"
             .parse()
-            .expect("hard-coded address must parse");
-        let bound = start_server(addr, state.clone(), auth_token.to_string()).await?;
+            .expect("hard-coded address must parse"); // safety: constant literal
+        let bound = start_server(addr, state.clone(), auth).await?;
+        Ok((bound, state))
+    }
+
+    /// Build the state and start a gateway server with multi-user auth.
+    /// Returns the bound address and the shared state.
+    pub async fn start_multi(
+        self,
+        auth: MultiAuthState,
+    ) -> Result<(SocketAddr, Arc<GatewayState>), crate::error::ChannelError> {
+        let state = self.build();
+        let addr: SocketAddr = "127.0.0.1:0"
+            .parse()
+            .expect("hard-coded address must parse"); // safety: constant literal
+        let bound = start_server(addr, state.clone(), auth).await?;
         Ok((bound, state))
     }
 }

src/channels/web/tests/mod.rs

@@ -0,0 +1,3 @@
+//! Integration tests for the web gateway module.
+
+mod multi_tenant;

src/channels/web/tests/multi_tenant.rs

@@ -0,0 +1,833 @@
+//! Multi-tenant isolation tests for the web gateway.
+//!
+//! Tests cover workspace pool scoping, job handler isolation, and auth
+//! enforcement on protected endpoints. Uses `LibSqlBackend::new_local()`
+//! with a temporary directory for a real (but ephemeral) database.
+
+use std::collections::HashMap;
+use std::sync::Arc;
+use std::time::Duration;
+
+use axum::Router;
+use axum::body::Body;
+use axum::http::{Method, Request, StatusCode};
+use axum::middleware;
+use axum::routing::{delete, get, post};
+use tower::ServiceExt;
+use uuid::Uuid;
+
+use crate::channels::web::GatewayChannel;
+use crate::channels::web::auth::{
+    AuthenticatedUser, MultiAuthState, UserIdentity, auth_middleware,
+};
+use crate::channels::web::server::{
+    ActiveConfigSnapshot, GatewayState, PerUserRateLimiter, PromptQueue, RateLimiter, WorkspacePool,
+};
+use crate::channels::web::sse::SseManager;
+use crate::config::GatewayConfig;
+
+// ── Helpers ────────────────────────────────────────────────────────────
+
+/// Create a two-user `MultiAuthState` for alice and bob.
+fn two_user_auth() -> MultiAuthState {
+    let mut tokens = HashMap::new();
+    tokens.insert(
+        "tok-alice".to_string(),
+        UserIdentity {
+            user_id: "alice".to_string(),
+            workspace_read_scopes: vec!["shared".to_string()],
+        },
+    );
+    tokens.insert(
+        "tok-bob".to_string(),
+        UserIdentity {
+            user_id: "bob".to_string(),
+            workspace_read_scopes: vec!["shared".to_string(), "alice".to_string()],
+        },
+    );
+    MultiAuthState::multi(tokens)
+}
+
+/// Build a `GatewayState` with configurable store and prompt queue.
+fn build_state(
+    store: Option<Arc<dyn crate::db::Database>>,
+    prompt_queue: Option<PromptQueue>,
+) -> Arc<GatewayState> {
+    Arc::new(GatewayState {
+        msg_tx: tokio::sync::RwLock::new(None),
+        sse: Arc::new(SseManager::new()),
+        workspace: None,
+        workspace_pool: None,
+        session_manager: None,
+        log_broadcaster: None,
+        log_level_handle: None,
+        extension_manager: None,
+        tool_registry: None,
+        store,
+        job_manager: None,
+        prompt_queue,
+        owner_id: "test".to_string(),
+        default_sender_id: "test".to_string(),
+        shutdown_tx: tokio::sync::RwLock::new(None),
+        ws_tracker: None,
+        llm_provider: None,
+        skill_registry: None,
+        skill_catalog: None,
+        scheduler: None,
+        chat_rate_limiter: PerUserRateLimiter::new(30, 60),
+        oauth_rate_limiter: RateLimiter::new(10, 60),
+        webhook_rate_limiter: RateLimiter::new(10, 60),
+        registry_entries: Vec::new(),
+        cost_guard: None,
+        routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
+        startup_time: std::time::Instant::now(),
+        active_config: ActiveConfigSnapshot::default(),
+    })
+}
+
+fn gateway_config() -> GatewayConfig {
+    GatewayConfig {
+        host: "127.0.0.1".to_string(),
+        port: 3000,
+        auth_token: Some("gateway-auth".to_string()),
+        user_id: "gateway-sender".to_string(),
+        workspace_read_scopes: Vec::new(),
+        memory_layers: Vec::new(),
+        user_tokens: None,
+    }
+}
+
+#[test]
+fn with_owner_scope_updates_gateway_owner_scope_in_multi_user_mode() {
+    let mut gateway = GatewayChannel::new(gateway_config());
+    gateway.auth = two_user_auth();
+    gateway.config.user_tokens = Some(HashMap::new());
+    let gateway = gateway.with_owner_scope("owner-scope");
+
+    assert_eq!(gateway.state.owner_id, "owner-scope");
+    assert_eq!(gateway.state.default_sender_id, "gateway-sender");
+
+    let alice = gateway
+        .auth
+        .authenticate("tok-alice")
+        .expect("alice token should remain valid");
+    let bob = gateway
+        .auth
+        .authenticate("tok-bob")
+        .expect("bob token should remain valid");
+    assert_eq!(alice.user_id, "alice");
+    assert_eq!(bob.user_id, "bob");
+}
+
+/// Create a libSQL-backed test database in a temporary directory.
+///
+/// Returns the database and a `TempDir` guard — the database file is
+/// deleted when the guard is dropped.
+#[cfg(feature = "libsql")]
+async fn test_db() -> (Arc<dyn crate::db::Database>, tempfile::TempDir) {
+    use crate::db::Database;
+    let dir = tempfile::tempdir().expect("failed to create temp dir"); // safety: test-only
+    let path = dir.path().join("test.db");
+    let backend = crate::db::libsql::LibSqlBackend::new_local(&path)
+        .await
+        .expect("failed to create test LibSqlBackend"); // safety: test-only
+    backend
+        .run_migrations()
+        .await
+        .expect("failed to run migrations"); // safety: test-only
+    (Arc::new(backend) as Arc<dyn crate::db::Database>, dir)
+}
+
+/// Build a minimal Routine for testing.
+fn make_routine(user_id: &str, name: &str) -> crate::agent::routine::Routine {
+    let now = chrono::Utc::now();
+    crate::agent::routine::Routine {
+        id: Uuid::new_v4(),
+        name: name.to_string(),
+        description: format!("Test routine: {name}"),
+        user_id: user_id.to_string(),
+        enabled: true,
+        trigger: crate::agent::routine::Trigger::Cron {
+            schedule: "0 9 * * *".to_string(),
+            timezone: None,
+        },
+        action: crate::agent::routine::RoutineAction::Lightweight {
+            prompt: "hello".to_string(),
+            context_paths: vec![],
+            max_tokens: 1024,
+            use_tools: false,
+            max_tool_rounds: 3,
+        },
+        guardrails: crate::agent::routine::RoutineGuardrails {
+            cooldown: Duration::from_secs(60),
+            max_concurrent: 1,
+            dedup_window: None,
+        },
+        notify: crate::agent::routine::NotifyConfig {
+            channel: None,
+            user: None,
+            on_success: false,
+            on_failure: true,
+            on_attention: true,
+        },
+        last_run_at: None,
+        next_fire_at: None,
+        run_count: 0,
+        consecutive_failures: 0,
+        state: serde_json::json!({}),
+        created_at: now,
+        updated_at: now,
+    }
+}
+
+/// Build a minimal SandboxJobRecord for testing.
+fn make_sandbox_job(user_id: &str, task: &str) -> crate::history::SandboxJobRecord {
+    let now = chrono::Utc::now();
+    crate::history::SandboxJobRecord {
+        id: Uuid::new_v4(),
+        task: task.to_string(),
+        status: "completed".to_string(),
+        user_id: user_id.to_string(),
+        project_dir: format!("/tmp/test-{}", Uuid::new_v4()),
+        success: Some(true),
+        failure_reason: None,
+        created_at: now,
+        started_at: Some(now),
+        completed_at: Some(now),
+        credential_grants_json: "[]".to_string(),
+    }
+}
+
+// ═══════════════════════════════════════════════════════════════════════
+// WorkspacePool Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+#[cfg(feature = "libsql")]
+mod workspace_pool {
+    use super::*;
+    use crate::config::{WorkspaceConfig, WorkspaceSearchConfig};
+    use crate::workspace::EmbeddingCacheConfig;
+    use crate::workspace::layer::MemoryLayer;
+
+    #[tokio::test]
+    async fn test_workspace_pool_applies_search_config() {
+        let (db, _dir) = test_db().await;
+        let search_config = WorkspaceSearchConfig {
+            rrf_k: 42,
+            ..Default::default()
+        };
+        let pool = WorkspacePool::new(
+            db,
+            None,
+            EmbeddingCacheConfig::default(),
+            search_config,
+            WorkspaceConfig::default(),
+        );
+        let identity = UserIdentity {
+            user_id: "alice".to_string(),
+            workspace_read_scopes: vec![],
+        };
+        let ws = pool.get_or_create(&identity).await;
+        assert_eq!(ws.user_id(), "alice");
+    }
+
+    #[tokio::test]
+    async fn test_workspace_pool_applies_memory_layers() {
+        let (db, _dir) = test_db().await;
+        let layers = vec![MemoryLayer {
+            name: "shared-layer".to_string(),
+            scope: "shared".to_string(),
+            writable: false,
+            sensitivity: Default::default(),
+        }];
+        let ws_config = WorkspaceConfig {
+            memory_layers: layers,
+            read_scopes: vec![],
+        };
+        let pool = WorkspacePool::new(
+            db,
+            None,
+            EmbeddingCacheConfig::default(),
+            WorkspaceSearchConfig::default(),
+            ws_config,
+        );
+        let identity = UserIdentity {
+            user_id: "alice".to_string(),
+            workspace_read_scopes: vec![],
+        };
+        let ws = pool.get_or_create(&identity).await;
+        // Memory layer scope "shared" should appear in read_user_ids.
+        assert!(
+            ws.read_user_ids().contains(&"shared".to_string()),
+            "expected 'shared' in read_user_ids, got {:?}",
+            ws.read_user_ids()
+        );
+    }
+
+    #[tokio::test]
+    async fn test_workspace_pool_applies_identity_read_scopes() {
+        let (db, _dir) = test_db().await;
+        let pool = WorkspacePool::new(
+            db,
+            None,
+            EmbeddingCacheConfig::default(),
+            WorkspaceSearchConfig::default(),
+            WorkspaceConfig::default(),
+        );
+        let identity = UserIdentity {
+            user_id: "bob".to_string(),
+            workspace_read_scopes: vec!["alice".to_string(), "shared".to_string()],
+        };
+        let ws = pool.get_or_create(&identity).await;
+        assert_eq!(ws.user_id(), "bob");
+        assert!(
+            ws.read_user_ids().contains(&"alice".to_string()),
+            "expected 'alice' in read_user_ids from identity scopes"
+        );
+        assert!(
+            ws.read_user_ids().contains(&"shared".to_string()),
+            "expected 'shared' in read_user_ids from identity scopes"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_workspace_pool_caches_per_user() {
+        let (db, _dir) = test_db().await;
+        let pool = WorkspacePool::new(
+            db,
+            None,
+            EmbeddingCacheConfig::default(),
+            WorkspaceSearchConfig::default(),
+            WorkspaceConfig::default(),
+        );
+        let alice_id = UserIdentity {
+            user_id: "alice".to_string(),
+            workspace_read_scopes: vec![],
+        };
+        let bob_id = UserIdentity {
+            user_id: "bob".to_string(),
+            workspace_read_scopes: vec![],
+        };
+
+        let alice_ws1 = pool.get_or_create(&alice_id).await;
+        let alice_ws2 = pool.get_or_create(&alice_id).await;
+        let bob_ws = pool.get_or_create(&bob_id).await;
+
+        // Same user gets the same Arc.
+        assert!(Arc::ptr_eq(&alice_ws1, &alice_ws2));
+        // Different users get different instances.
+        assert!(!Arc::ptr_eq(&alice_ws1, &bob_ws));
+        assert_eq!(alice_ws1.user_id(), "alice");
+        assert_eq!(bob_ws.user_id(), "bob");
+    }
+
+    #[tokio::test]
+    async fn test_workspace_pool_combines_global_and_identity_scopes() {
+        let (db, _dir) = test_db().await;
+        let ws_config = WorkspaceConfig {
+            memory_layers: vec![],
+            read_scopes: vec!["global-shared".to_string()],
+        };
+        let pool = WorkspacePool::new(
+            db,
+            None,
+            EmbeddingCacheConfig::default(),
+            WorkspaceSearchConfig::default(),
+            ws_config,
+        );
+        let identity = UserIdentity {
+            user_id: "alice".to_string(),
+            workspace_read_scopes: vec!["token-scope".to_string()],
+        };
+        let ws = pool.get_or_create(&identity).await;
+        let scopes = ws.read_user_ids();
+        // Primary scope
+        assert!(scopes.contains(&"alice".to_string()));
+        // Global config scope
+        assert!(
+            scopes.contains(&"global-shared".to_string()),
+            "expected global scope 'global-shared', got {:?}",
+            scopes
+        );
+        // Token identity scope
+        assert!(
+            scopes.contains(&"token-scope".to_string()),
+            "expected token scope 'token-scope', got {:?}",
+            scopes
+        );
+    }
+}
+
+// ═══════════════════════════════════════════════════════════════════════
+// Jobs Handler Isolation Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+#[cfg(feature = "libsql")]
+mod jobs_isolation {
+    use super::*;
+    use crate::channels::web::handlers::jobs::{
+        jobs_cancel_handler, jobs_prompt_handler, jobs_restart_handler, jobs_summary_handler,
+    };
+    // SandboxStore methods are accessed through the Database supertrait.
+
+    /// Build a router with job endpoints behind multi-user auth.
+    fn jobs_router(state: Arc<GatewayState>, auth: MultiAuthState) -> Router {
+        Router::new()
+            .route("/api/jobs/summary", get(jobs_summary_handler))
+            .route("/api/jobs/{id}/cancel", post(jobs_cancel_handler))
+            .route("/api/jobs/{id}/restart", post(jobs_restart_handler))
+            .route("/api/jobs/{id}/prompt", post(jobs_prompt_handler))
+            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .with_state(state)
+    }
+
+    #[tokio::test]
+    async fn test_jobs_summary_scoped_to_user() {
+        let (db, _dir) = test_db().await;
+
+        // Insert sandbox jobs for alice and bob.
+        let alice_job = make_sandbox_job("alice", "alice task");
+        let bob_job = make_sandbox_job("bob", "bob task");
+        db.save_sandbox_job(&alice_job).await.unwrap();
+        db.save_sandbox_job(&bob_job).await.unwrap();
+
+        let state = build_state(Some(db), None);
+        let auth = two_user_auth();
+        let app = jobs_router(state, auth);
+
+        // Alice should see 1 job.
+        let req = Request::builder()
+            .uri("/api/jobs/summary")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body: serde_json::Value =
+            serde_json::from_slice(&axum::body::to_bytes(resp.into_body(), 4096).await.unwrap())
+                .unwrap();
+        assert_eq!(body["total"], 1, "alice should see only her own jobs");
+
+        // Bob should see 1 job.
+        let req = Request::builder()
+            .uri("/api/jobs/summary")
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body: serde_json::Value =
+            serde_json::from_slice(&axum::body::to_bytes(resp.into_body(), 4096).await.unwrap())
+                .unwrap();
+        assert_eq!(body["total"], 1, "bob should see only his own jobs");
+    }
+
+    #[tokio::test]
+    async fn test_jobs_restart_rejects_other_user() {
+        let (db, _dir) = test_db().await;
+
+        // Insert a failed sandbox job owned by alice.
+        let mut alice_job = make_sandbox_job("alice", "alice task");
+        alice_job.status = "failed".to_string();
+        alice_job.success = Some(false);
+        db.save_sandbox_job(&alice_job).await.unwrap();
+
+        let state = build_state(Some(db), None);
+        let auth = two_user_auth();
+        let app = jobs_router(state, auth);
+
+        // Bob tries to restart alice's job.
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri(format!("/api/jobs/{}/restart", alice_job.id))
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not be able to restart alice's job"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_jobs_prompt_works_for_agent_jobs() {
+        let (db, _dir) = test_db().await;
+
+        // Insert a running sandbox job owned by alice in claude_code mode.
+        let mut alice_job = make_sandbox_job("alice", "prompt test");
+        alice_job.status = "running".to_string();
+        alice_job.success = None;
+        alice_job.completed_at = None;
+        db.save_sandbox_job(&alice_job).await.unwrap();
+        db.update_sandbox_job_mode(alice_job.id, "claude_code")
+            .await
+            .unwrap();
+
+        let prompt_queue: PromptQueue =
+            Arc::new(tokio::sync::Mutex::new(std::collections::HashMap::new()));
+        let state = build_state(Some(db), Some(prompt_queue.clone()));
+        let auth = two_user_auth();
+        let app = jobs_router(state, auth);
+
+        // Alice prompts her own job.
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri(format!("/api/jobs/{}/prompt", alice_job.id))
+            .header("Authorization", "Bearer tok-alice")
+            .header("Content-Type", "application/json")
+            .body(Body::from(
+                serde_json::to_string(&serde_json::json!({"content": "hello"})).unwrap(),
+            ))
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::OK,
+            "alice should be able to prompt her own job"
+        );
+
+        // Verify prompt was enqueued.
+        let queue = prompt_queue.lock().await;
+        assert!(
+            queue.contains_key(&alice_job.id),
+            "prompt queue should contain alice's job"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_jobs_prompt_rejects_other_user() {
+        let (db, _dir) = test_db().await;
+
+        let mut alice_job = make_sandbox_job("alice", "alice task");
+        alice_job.status = "running".to_string();
+        alice_job.success = None;
+        alice_job.completed_at = None;
+        db.save_sandbox_job(&alice_job).await.unwrap();
+        db.update_sandbox_job_mode(alice_job.id, "claude_code")
+            .await
+            .unwrap();
+
+        let prompt_queue: PromptQueue =
+            Arc::new(tokio::sync::Mutex::new(std::collections::HashMap::new()));
+        let state = build_state(Some(db), Some(prompt_queue));
+        let auth = two_user_auth();
+        let app = jobs_router(state, auth);
+
+        // Bob tries to prompt alice's job.
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri(format!("/api/jobs/{}/prompt", alice_job.id))
+            .header("Authorization", "Bearer tok-bob")
+            .header("Content-Type", "application/json")
+            .body(Body::from(
+                serde_json::to_string(&serde_json::json!({"content": "sneaky"})).unwrap(),
+            ))
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not be able to prompt alice's job"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_jobs_cancel_rejects_other_user() {
+        let (db, _dir) = test_db().await;
+
+        let mut alice_job = make_sandbox_job("alice", "alice running");
+        alice_job.status = "running".to_string();
+        alice_job.success = None;
+        alice_job.completed_at = None;
+        db.save_sandbox_job(&alice_job).await.unwrap();
+
+        let state = build_state(Some(db), None);
+        let auth = two_user_auth();
+        let app = jobs_router(state, auth);
+
+        // Bob tries to cancel alice's job.
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri(format!("/api/jobs/{}/cancel", alice_job.id))
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not be able to cancel alice's job"
+        );
+    }
+}
+
+// ═══════════════════════════════════════════════════════════════════════
+// Routines Isolation Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+#[cfg(feature = "libsql")]
+mod routines_isolation {
+    use super::*;
+    use crate::channels::web::handlers::routines::{
+        routines_delete_handler, routines_detail_handler, routines_list_handler,
+        routines_summary_handler, routines_toggle_handler,
+    };
+    // RoutineStore methods are accessed through the Database supertrait.
+
+    fn routines_router(state: Arc<GatewayState>, auth: MultiAuthState) -> Router {
+        Router::new()
+            .route("/api/routines", get(routines_list_handler))
+            .route("/api/routines/summary", get(routines_summary_handler))
+            .route("/api/routines/{id}", get(routines_detail_handler))
+            .route("/api/routines/{id}/toggle", post(routines_toggle_handler))
+            .route("/api/routines/{id}", delete(routines_delete_handler))
+            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .with_state(state)
+    }
+
+    #[tokio::test]
+    async fn test_routines_isolation() {
+        let (db, _dir) = test_db().await;
+
+        // Create routines for alice and bob.
+        let alice_routine = make_routine("alice", "alice-daily");
+        let bob_routine = make_routine("bob", "bob-daily");
+        db.create_routine(&alice_routine).await.unwrap();
+        db.create_routine(&bob_routine).await.unwrap();
+
+        let state = build_state(Some(db), None);
+        let auth = two_user_auth();
+        let app = routines_router(state, auth);
+
+        // Alice sees only her routine in the list.
+        let req = Request::builder()
+            .uri("/api/routines")
+            .header("Authorization", "Bearer tok-alice")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body: serde_json::Value =
+            serde_json::from_slice(&axum::body::to_bytes(resp.into_body(), 8192).await.unwrap())
+                .unwrap();
+        let routines = body["routines"].as_array().unwrap();
+        assert_eq!(routines.len(), 1, "alice should see only her routines");
+        assert_eq!(routines[0]["name"], "alice-daily");
+
+        // Bob sees only his routine.
+        let req = Request::builder()
+            .uri("/api/routines")
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+        let body: serde_json::Value =
+            serde_json::from_slice(&axum::body::to_bytes(resp.into_body(), 8192).await.unwrap())
+                .unwrap();
+        let routines = body["routines"].as_array().unwrap();
+        assert_eq!(routines.len(), 1, "bob should see only his routines");
+        assert_eq!(routines[0]["name"], "bob-daily");
+
+        // Bob cannot view alice's routine detail.
+        let req = Request::builder()
+            .uri(format!("/api/routines/{}", alice_routine.id))
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not see alice's routine detail"
+        );
+
+        // Bob cannot toggle alice's routine.
+        let req = Request::builder()
+            .method(Method::POST)
+            .uri(format!("/api/routines/{}/toggle", alice_routine.id))
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not toggle alice's routine"
+        );
+
+        // Bob cannot delete alice's routine.
+        let req = Request::builder()
+            .method(Method::DELETE)
+            .uri(format!("/api/routines/{}", alice_routine.id))
+            .header("Authorization", "Bearer tok-bob")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::NOT_FOUND,
+            "bob should not delete alice's routine"
+        );
+    }
+}
+
+// ═══════════════════════════════════════════════════════════════════════
+// Handler Auth Enforcement Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+mod auth_enforcement {
+    use super::*;
+
+    /// Dummy handler that extracts `AuthenticatedUser` — if the auth middleware
+    /// rejects the request, this handler is never reached.
+    async fn authed_handler(AuthenticatedUser(_user): AuthenticatedUser) -> &'static str {
+        "ok"
+    }
+
+    /// Build a router with the real auth middleware and dummy handlers at all
+    /// the paths we want to verify require authentication.
+    fn auth_test_router(auth: MultiAuthState) -> Router {
+        let state = build_state(None, None);
+        Router::new()
+            // Routines
+            .route("/api/routines", get(authed_handler))
+            .route("/api/routines/summary", get(authed_handler))
+            .route("/api/routines/{id}", get(authed_handler))
+            .route("/api/routines/{id}/toggle", post(authed_handler))
+            .route("/api/routines/{id}", delete(authed_handler))
+            // Skills
+            .route("/api/skills", get(authed_handler))
+            .route("/api/skills/search", post(authed_handler))
+            .route("/api/skills/install", post(authed_handler))
+            .route("/api/skills/{name}", delete(authed_handler))
+            // Logs
+            .route("/api/logs/events", get(authed_handler))
+            .route("/api/logs/level", get(authed_handler).put(authed_handler))
+            // Gateway status
+            .route("/api/gateway/status", get(authed_handler))
+            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .with_state(state)
+    }
+
+    /// Send a request without auth and assert it returns UNAUTHORIZED.
+    async fn assert_requires_auth(app: &Router, method: Method, uri: &str) {
+        let req = Request::builder()
+            .method(method.clone())
+            .uri(uri)
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::UNAUTHORIZED,
+            "{} {} should require auth",
+            method,
+            uri
+        );
+    }
+
+    /// Send a request with a valid token and assert it succeeds.
+    async fn assert_passes_with_token(app: &Router, method: Method, uri: &str, token: &str) {
+        let req = Request::builder()
+            .method(method.clone())
+            .uri(uri)
+            .header("Authorization", format!("Bearer {token}"))
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::OK,
+            "{} {} should pass with valid token",
+            method,
+            uri
+        );
+    }
+
+    #[tokio::test]
+    async fn test_routines_handlers_require_auth() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+        let id = Uuid::new_v4();
+
+        assert_requires_auth(&app, Method::GET, "/api/routines").await;
+        assert_requires_auth(&app, Method::GET, "/api/routines/summary").await;
+        assert_requires_auth(&app, Method::GET, &format!("/api/routines/{id}")).await;
+        assert_requires_auth(&app, Method::POST, &format!("/api/routines/{id}/toggle")).await;
+        assert_requires_auth(&app, Method::DELETE, &format!("/api/routines/{id}")).await;
+    }
+
+    #[tokio::test]
+    async fn test_skills_handlers_require_auth() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+
+        assert_requires_auth(&app, Method::GET, "/api/skills").await;
+        assert_requires_auth(&app, Method::POST, "/api/skills/search").await;
+        assert_requires_auth(&app, Method::POST, "/api/skills/install").await;
+        assert_requires_auth(&app, Method::DELETE, "/api/skills/test-skill").await;
+    }
+
+    #[tokio::test]
+    async fn test_logs_handlers_require_auth() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+
+        assert_requires_auth(&app, Method::GET, "/api/logs/events").await;
+        assert_requires_auth(&app, Method::GET, "/api/logs/level").await;
+        assert_requires_auth(&app, Method::PUT, "/api/logs/level").await;
+    }
+
+    #[tokio::test]
+    async fn test_gateway_status_requires_auth() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+
+        assert_requires_auth(&app, Method::GET, "/api/gateway/status").await;
+    }
+
+    #[tokio::test]
+    async fn test_valid_token_passes_all_endpoints() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+        let id = Uuid::new_v4();
+
+        assert_passes_with_token(&app, Method::GET, "/api/routines", "secret-tok").await;
+        assert_passes_with_token(&app, Method::GET, "/api/skills", "secret-tok").await;
+        assert_passes_with_token(&app, Method::GET, "/api/logs/events", "secret-tok").await;
+        assert_passes_with_token(&app, Method::GET, "/api/gateway/status", "secret-tok").await;
+        assert_passes_with_token(
+            &app,
+            Method::GET,
+            &format!("/api/routines/{id}"),
+            "secret-tok",
+        )
+        .await;
+    }
+
+    #[tokio::test]
+    async fn test_wrong_token_rejected_on_all_endpoints() {
+        let auth = MultiAuthState::single("secret-tok".to_string(), "user".to_string());
+        let app = auth_test_router(auth);
+
+        // Wrong token should be rejected.
+        let req = Request::builder()
+            .uri("/api/routines")
+            .header("Authorization", "Bearer wrong-tok")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+
+        let req = Request::builder()
+            .uri("/api/gateway/status")
+            .header("Authorization", "Bearer wrong-tok")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+    }
+}

src/channels/web/ws.rs

@@ -62,7 +62,11 @@ impl Default for WsConnectionTracker {
 ///
 /// When either task ends (client disconnect or broadcast closed), both are
 /// cleaned up.
-pub async fn handle_ws_connection(socket: WebSocket, state: Arc<GatewayState>) {
+pub async fn handle_ws_connection(
+    socket: WebSocket,
+    state: Arc<GatewayState>,
+    user: crate::channels::web::auth::UserIdentity,
+) {
     let (mut ws_sink, mut ws_stream) = socket.split();
 
     // Track connection
@@ -71,9 +75,9 @@ pub async fn handle_ws_connection(socket: WebSocket, state: Arc<GatewayState>) {
     }
     let tracker_for_drop = state.ws_tracker.clone();
 
-    // Subscribe to broadcast events (same source as SSE).
+    // Subscribe to broadcast events (same source as SSE), scoped to this user.
     // Reject if we've hit the connection limit.
-    let Some(raw_stream) = state.sse.subscribe_raw() else {
+    let Some(raw_stream) = state.sse.subscribe_raw(Some(user.user_id.clone())) else {
         tracing::warn!("WebSocket rejected: too many connections");
         // Decrement the WS tracker we already incremented above.
         if let Some(ref tracker) = tracker_for_drop {
@@ -117,7 +121,7 @@ pub async fn handle_ws_connection(socket: WebSocket, state: Arc<GatewayState>) {
     });
 
     // Receiver task: read client frames and route to agent
-    let user_id = state.user_id.clone();
+    let user_id = user.user_id;
     while let Some(Ok(frame)) = ws_stream.next().await {
         match frame {
             Message::Text(text) => {
@@ -263,10 +267,14 @@ async fn handle_client_message(
             token,
         } => {
             if let Some(ref ext_mgr) = state.extension_manager {
-                match ext_mgr.configure_token(&extension_name, &token).await {
+                match ext_mgr
+                    .configure_token(&extension_name, &token, user_id)
+                    .await
+                {
                     Ok(result) => {
                         if result.verification.is_some() {
-                            state.sse.broadcast(
+                            state.sse.broadcast_for_user(
+                                user_id,
                                 crate::channels::web::types::SseEvent::AuthRequired {
                                     extension_name: extension_name.clone(),
                                     instructions: Some(result.message),
@@ -275,8 +283,9 @@ async fn handle_client_message(
                                 },
                             );
                         } else {
-                            crate::channels::web::server::clear_auth_mode(state).await;
-                            state.sse.broadcast(
+                            crate::channels::web::server::clear_auth_mode(state, user_id).await;
+                            state.sse.broadcast_for_user(
+                                user_id,
                                 crate::channels::web::types::SseEvent::AuthCompleted {
                                     extension_name,
                                     success: true,
@@ -288,7 +297,8 @@ async fn handle_client_message(
                     Err(e) => {
                         let msg = format!("Auth failed: {}", e);
                         if matches!(e, crate::extensions::ExtensionError::ValidationFailed(_)) {
-                            state.sse.broadcast(
+                            state.sse.broadcast_for_user(
+                                user_id,
                                 crate::channels::web::types::SseEvent::AuthRequired {
                                     extension_name: extension_name.clone(),
                                     instructions: Some(msg.clone()),
@@ -311,7 +321,7 @@ async fn handle_client_message(
             }
         }
         WsClientMessage::AuthCancel { .. } => {
-            crate::channels::web::server::clear_auth_mode(state).await;
+            crate::channels::web::server::clear_auth_mode(state, user_id).await;
         }
         WsClientMessage::Ping => {
             let _ = direct_tx.send(WsServerMessage::Pong).await;
@@ -498,8 +508,9 @@ mod tests {
 
         GatewayState {
             msg_tx: tokio::sync::RwLock::new(msg_tx),
-            sse: SseManager::new(),
+            sse: Arc::new(SseManager::new()),
             workspace: None,
+            workspace_pool: None,
             session_manager: None,
             log_broadcaster: None,
             log_level_handle: None,
@@ -509,13 +520,14 @@ mod tests {
             job_manager: None,
             prompt_queue: None,
             scheduler: None,
-            user_id: "test".to_string(),
+            owner_id: "test".to_string(),
+            default_sender_id: "test".to_string(),
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
             llm_provider: None,
             skill_registry: None,
             skill_catalog: None,
-            chat_rate_limiter: crate::channels::web::server::RateLimiter::new(30, 60),
+            chat_rate_limiter: crate::channels::web::server::PerUserRateLimiter::new(30, 60),
             oauth_rate_limiter: crate::channels::web::server::RateLimiter::new(10, 60),
             webhook_rate_limiter: crate::channels::web::server::RateLimiter::new(10, 60),
             registry_entries: Vec::new(),

src/cli/oauth_defaults.rs

@@ -62,6 +62,30 @@ pub fn builtin_client_id_override_env(secret_name: &str) -> Option<&'static str>
     }
 }
 
+/// Suppress the baked-in desktop OAuth client secret when a hosted proxy is configured.
+///
+/// In hosted deployments, IronClaw may resolve the platform Google client ID from
+/// environment variables while still falling back to the baked-in desktop secret.
+/// That client_id/client_secret mismatch breaks Google token exchange and refresh.
+///
+/// When the proxy is configured, the platform will inject the correct server-side
+/// secret for matching platform credentials, so the baked-in secret must be omitted.
+pub fn hosted_proxy_client_secret(
+    client_secret: &Option<String>,
+    builtin: Option<&OAuthCredentials>,
+    exchange_proxy_configured: bool,
+) -> Option<String> {
+    if !exchange_proxy_configured {
+        return client_secret.clone();
+    }
+
+    let builtin_secret = builtin.map(|credentials| credentials.client_secret);
+    match (client_secret, builtin_secret) {
+        (Some(resolved), Some(baked_in)) if resolved == baked_in => None,
+        _ => client_secret.clone(),
+    }
+}
+
 // ── Shared callback server ──────────────────────────────────────────────
 
 // Core OAuth callback infrastructure is defined in `crate::llm::oauth_helpers`
@@ -447,8 +471,8 @@ pub struct PendingOAuthFlow {
     pub user_id: String,
     /// Secrets store reference for token persistence.
     pub secrets: Arc<dyn SecretsStore + Send + Sync>,
-    /// SSE broadcast sender for notifying the web UI.
-    pub sse_sender: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
+    /// SSE broadcast manager for notifying the web UI.
+    pub sse_manager: Option<Arc<crate::channels::web::sse::SseManager>>,
     /// Gateway auth token for authenticating with the platform token exchange proxy.
     pub gateway_token: Option<String>,
     /// Additional form params for the token exchange request.
@@ -661,6 +685,48 @@ pub struct ProxyTokenExchangeRequest<'a> {
     pub extra_token_params: &'a HashMap<String, String>,
 }
 
+pub struct ProxyRefreshTokenRequest<'a> {
+    pub proxy_url: &'a str,
+    pub gateway_token: &'a str,
+    pub token_url: &'a str,
+    pub client_id: &'a str,
+    pub client_secret: Option<&'a str>,
+    pub refresh_token: &'a str,
+    pub provider: Option<&'a str>,
+}
+
+fn oauth_token_response_from_json(
+    token_data: serde_json::Value,
+    access_token_field: &str,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    let access_token = token_data
+        .get(access_token_field)
+        .and_then(|v| v.as_str())
+        .ok_or_else(|| {
+            let fields: Vec<&str> = token_data
+                .as_object()
+                .map(|o| o.keys().map(|k| k.as_str()).collect())
+                .unwrap_or_default();
+            OAuthCallbackError::Io(format!(
+                "No '{}' field in proxy response (fields present: {:?})",
+                access_token_field, fields
+            ))
+        })?
+        .to_string();
+
+    let refresh_token = token_data
+        .get("refresh_token")
+        .and_then(|v| v.as_str())
+        .map(String::from);
+    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
+
+    Ok(OAuthTokenResponse {
+        access_token,
+        refresh_token,
+        expires_in,
+    })
+}
+
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
 /// Authenticated via the gateway auth token (Bearer header). The caller may
@@ -682,6 +748,7 @@ pub async fn exchange_via_proxy(
 
     let client = reqwest::Client::builder()
         .timeout(Duration::from_secs(60))
+        .redirect(reqwest::redirect::Policy::none())
         .build()
         .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
     let mut params = vec![
@@ -724,41 +791,350 @@ pub async fn exchange_via_proxy(
         .json()
         .await
         .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
+    oauth_token_response_from_json(token_data, request.access_token_field)
+}
 
-    let access_token = token_data
-        .get(request.access_token_field)
-        .and_then(|v| v.as_str())
-        .ok_or_else(|| {
-            let fields: Vec<&str> = token_data
-                .as_object()
-                .map(|o| o.keys().map(|k| k.as_str()).collect())
-                .unwrap_or_default();
-            OAuthCallbackError::Io(format!(
-                "No '{}' field in proxy response (fields present: {:?})",
-                request.access_token_field, fields
-            ))
-        })?
-        .to_string();
+/// Refresh an OAuth access token via the platform's token refresh proxy.
+///
+/// Authenticated via the gateway auth token (Bearer header). The caller may
+/// either rely on proxy-side secret lookup or forward a `client_secret` when
+/// the provider requires it.
+pub async fn refresh_token_via_proxy(
+    request: ProxyRefreshTokenRequest<'_>,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    if request.gateway_token.is_empty() {
+        return Err(OAuthCallbackError::Io(
+            "Gateway auth token is required for proxy token refresh".to_string(),
+        ));
+    }
 
-    let refresh_token = token_data
-        .get("refresh_token")
-        .and_then(|v| v.as_str())
-        .map(String::from);
-    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
+    let refresh_url = format!("{}/oauth/refresh", request.proxy_url.trim_end_matches('/'));
+    let client = reqwest::Client::builder()
+        .timeout(Duration::from_secs(15))
+        .redirect(reqwest::redirect::Policy::none())
+        .build()
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
 
-    Ok(OAuthTokenResponse {
-        access_token,
-        refresh_token,
-        expires_in,
-    })
+    let mut params = vec![
+        ("refresh_token", request.refresh_token.to_string()),
+        ("token_url", request.token_url.to_string()),
+        ("client_id", request.client_id.to_string()),
+    ];
+    if let Some(secret) = request.client_secret {
+        params.push(("client_secret", secret.to_string()));
+    }
+    if let Some(provider) = request.provider {
+        params.push(("provider", provider.to_string()));
+    }
+
+    let response = client
+        .post(&refresh_url)
+        .bearer_auth(request.gateway_token)
+        .form(&params)
+        .send()
+        .await
+        .map_err(|e| {
+            OAuthCallbackError::Io(format!("Token refresh proxy request failed: {}", e))
+        })?;
+
+    if !response.status().is_success() {
+        let status = response.status();
+        let body = response.text().await.unwrap_or_default();
+        return Err(OAuthCallbackError::Io(format!(
+            "Token refresh proxy failed: {} - {}",
+            status, body
+        )));
+    }
+
+    let token_data: serde_json::Value = response
+        .json()
+        .await
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
+
+    oauth_token_response_from_json(token_data, "access_token")
 }
 
 #[cfg(test)]
 mod tests {
+    use std::collections::HashMap;
+    use std::net::SocketAddr;
+    use std::sync::Arc;
+
+    use axum::extract::{Form, State};
+    use axum::http::HeaderMap;
+    use axum::response::Redirect;
+    use axum::routing::post;
+    use axum::{Json, Router};
+    use serde_json::json;
+    use tokio::net::TcpListener;
+    use tokio::sync::{Mutex, oneshot};
+
     use crate::cli::oauth_defaults::{
         builtin_credentials, callback_host, callback_url, is_loopback_host, landing_html,
     };
     use crate::config::helpers::lock_env;
+    use crate::testing::credentials::{TEST_OAUTH_CLIENT_ID, TEST_OAUTH_CLIENT_SECRET};
+
+    #[derive(Clone, Debug, PartialEq, Eq)]
+    struct RecordedProxyRequest {
+        authorization: Option<String>,
+        form: HashMap<String, String>,
+    }
+
+    #[derive(Clone)]
+    struct MockProxyState {
+        requests: Arc<Mutex<Vec<RecordedProxyRequest>>>,
+        exchange_redirect_target: String,
+        refresh_redirect_target: String,
+    }
+
+    struct MockProxyServer {
+        addr: SocketAddr,
+        requests: Arc<Mutex<Vec<RecordedProxyRequest>>>,
+        shutdown_tx: Option<oneshot::Sender<()>>,
+        server_task: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl MockProxyServer {
+        async fn start() -> Self {
+            async fn exchange_handler(
+                State(state): State<MockProxyState>,
+                headers: HeaderMap,
+                Form(form): Form<HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            async fn refresh_handler(
+                State(state): State<MockProxyState>,
+                headers: HeaderMap,
+                Form(form): Form<HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            async fn exchange_redirect_handler(State(state): State<MockProxyState>) -> Redirect {
+                Redirect::temporary(&state.exchange_redirect_target)
+            }
+
+            async fn refresh_redirect_handler(State(state): State<MockProxyState>) -> Redirect {
+                Redirect::temporary(&state.refresh_redirect_target)
+            }
+
+            let requests = Arc::new(Mutex::new(Vec::new()));
+            let listener = TcpListener::bind("127.0.0.1:0")
+                .await
+                .expect("bind mock proxy");
+            let addr = listener.local_addr().expect("read mock proxy addr");
+            let exchange_redirect_target = format!("http://{addr}/oauth/exchange");
+            let refresh_redirect_target = format!("http://{addr}/oauth/refresh");
+            let app = Router::new()
+                .route("/oauth/exchange", post(exchange_handler))
+                .route("/oauth/refresh", post(refresh_handler))
+                .route("/redirect/oauth/exchange", post(exchange_redirect_handler))
+                .route("/redirect/oauth/refresh", post(refresh_redirect_handler))
+                .with_state(MockProxyState {
+                    requests: Arc::clone(&requests),
+                    exchange_redirect_target,
+                    refresh_redirect_target,
+                });
+            let (shutdown_tx, shutdown_rx) = oneshot::channel::<()>();
+            let server_task = tokio::spawn(async move {
+                let _ = axum::serve(listener, app)
+                    .with_graceful_shutdown(async {
+                        let _ = shutdown_rx.await;
+                    })
+                    .await;
+            });
+
+            Self {
+                addr,
+                requests,
+                shutdown_tx: Some(shutdown_tx),
+                server_task: Some(server_task),
+            }
+        }
+
+        fn base_url(&self) -> String {
+            format!("http://{}", self.addr)
+        }
+
+        fn redirecting_base_url(&self) -> String {
+            format!("{}/redirect", self.base_url())
+        }
+
+        async fn requests(&self) -> Vec<RecordedProxyRequest> {
+            self.requests.lock().await.clone()
+        }
+
+        async fn shutdown(mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                let _ = task.await;
+            }
+        }
+    }
+
+    impl Drop for MockProxyServer {
+        fn drop(&mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                task.abort();
+            }
+        }
+    }
+
+    #[test]
+    fn test_hosted_proxy_client_secret_suppresses_builtin_secret() {
+        let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
+        let client_secret = Some(builtin.client_secret.to_string());
+
+        let result = super::hosted_proxy_client_secret(&client_secret, Some(&builtin), true);
+
+        assert_eq!(result, None);
+    }
+
+    #[test]
+    fn test_hosted_proxy_client_secret_preserves_explicit_secret() {
+        let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
+        let client_secret = Some("hosted-server-secret".to_string());
+
+        let result = super::hosted_proxy_client_secret(&client_secret, Some(&builtin), true);
+
+        assert_eq!(result, client_secret);
+    }
+
+    #[tokio::test]
+    async fn test_refresh_token_via_proxy_sends_auth_and_form() {
+        let server = MockProxyServer::start().await;
+
+        let response = super::refresh_token_via_proxy(super::ProxyRefreshTokenRequest {
+            proxy_url: &server.base_url(),
+            gateway_token: "gateway-test-token",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            refresh_token: "refresh-token-123",
+            provider: Some("google"),
+        })
+        .await
+        .expect("proxy refresh succeeds");
+
+        assert_eq!(response.access_token, "proxy-access-token");
+        assert_eq!(
+            response.refresh_token.as_deref(),
+            Some("proxy-refresh-token")
+        );
+        assert_eq!(response.expires_in, Some(7200));
+
+        let requests = server.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer gateway-test-token")
+        );
+        assert_eq!(
+            requests[0].form.get("token_url").map(String::as_str),
+            Some("https://oauth2.googleapis.com/token")
+        );
+        assert_eq!(
+            requests[0].form.get("client_id").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_ID)
+        );
+        assert_eq!(
+            requests[0].form.get("client_secret").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_SECRET)
+        );
+        assert_eq!(
+            requests[0].form.get("refresh_token").map(String::as_str),
+            Some("refresh-token-123")
+        );
+        assert_eq!(
+            requests[0].form.get("provider").map(String::as_str),
+            Some("google")
+        );
+
+        server.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_exchange_via_proxy_does_not_follow_redirects() {
+        let server = MockProxyServer::start().await;
+
+        let error = match super::exchange_via_proxy(super::ProxyTokenExchangeRequest {
+            proxy_url: &server.redirecting_base_url(),
+            gateway_token: "gateway-test-token",
+            code: "auth-code-123",
+            redirect_uri: "http://localhost:3000/oauth/callback",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            access_token_field: "access_token",
+            code_verifier: Some("code-verifier-123"),
+            extra_token_params: &HashMap::new(),
+        })
+        .await
+        {
+            Ok(_) => panic!("redirected proxy exchange should fail"),
+            Err(error) => error,
+        };
+
+        assert!(error.to_string().contains("307"));
+        assert!(server.requests().await.is_empty());
+
+        server.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_refresh_token_via_proxy_does_not_follow_redirects() {
+        let server = MockProxyServer::start().await;
+
+        let error = match super::refresh_token_via_proxy(super::ProxyRefreshTokenRequest {
+            proxy_url: &server.redirecting_base_url(),
+            gateway_token: "gateway-test-token",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            refresh_token: "refresh-token-123",
+            provider: Some("google"),
+        })
+        .await
+        {
+            Ok(_) => panic!("redirected proxy refresh should fail"),
+            Err(error) => error,
+        };
+
+        assert!(error.to_string().contains("307"));
+        assert!(server.requests().await.is_empty());
+
+        server.shutdown().await;
+    }
 
     #[test]
     fn test_is_loopback_host() {

src/cli/routines.rs

@@ -10,7 +10,7 @@ use clap::Subcommand;
 use uuid::Uuid;
 
 use crate::agent::routine::{
-    NotifyConfig, Routine, RoutineAction, RoutineGuardrails, Trigger, next_cron_fire,
+    NotifyConfig, Routine, RoutineAction, RoutineGuardrails, RunStatus, Trigger, next_cron_fire,
 };
 use crate::db::Database;
 
@@ -251,15 +251,26 @@ async fn list(
     );
     println!("{}", "-".repeat(130));
 
+    // Fetch last-run status for all routines in a single batch query
+    let routine_ids: Vec<Uuid> = filtered.iter().map(|r| r.id).collect();
+    let last_run_results = db
+        .batch_get_last_run_status(&routine_ids)
+        .await
+        .unwrap_or_default();
+
     for r in &filtered {
-        let status = if r.enabled {
-            if r.consecutive_failures > 0 {
-                format!("err({})", r.consecutive_failures)
-            } else {
-                "active".to_string()
-            }
-        } else {
+        let last_run_status = last_run_results.get(&r.id).copied();
+
+        let status = if !r.enabled {
             "disabled".to_string()
+        } else if last_run_status == Some(RunStatus::Running) {
+            "running".to_string()
+        } else if r.consecutive_failures > 0 {
+            format!("err({})", r.consecutive_failures)
+        } else if last_run_status == Some(RunStatus::Attention) {
+            "attention".to_string()
+        } else {
+            "active".to_string()
         };
 
         let next_fire = r

src/config/channels.rs

@@ -2,6 +2,7 @@ use std::collections::HashMap;
 use std::path::PathBuf;
 
 use secrecy::SecretString;
+use serde::Deserialize;
 
 use crate::bootstrap::ironclaw_base_dir;
 use crate::config::helpers::{optional_env, parse_bool_env, parse_optional_env};
@@ -45,6 +46,26 @@ pub struct GatewayConfig {
     /// Bearer token for authentication. Random hex generated at startup if unset.
     pub auth_token: Option<String>,
     pub user_id: String,
+    /// Additional user scopes for workspace reads.
+    ///
+    /// When set, the workspace will be able to read (search, read, list) from
+    /// these additional user scopes while writes remain isolated to `user_id`.
+    /// Parsed from `WORKSPACE_READ_SCOPES` (comma-separated).
+    pub workspace_read_scopes: Vec<String>,
+    /// Memory layer definitions (JSON in env var, or from external config).
+    pub memory_layers: Vec<crate::workspace::layer::MemoryLayer>,
+    /// Multi-user token map. When set, each token maps to a user identity.
+    /// Parsed from `GATEWAY_USER_TOKENS` (JSON string). When absent, falls back
+    /// to single-user mode via `auth_token` + `user_id`.
+    pub user_tokens: Option<HashMap<String, UserTokenConfig>>,
+}
+
+/// Per-user token configuration for multi-user mode.
+#[derive(Debug, Clone, Deserialize)]
+pub struct UserTokenConfig {
+    pub user_id: String,
+    #[serde(default)]
+    pub workspace_read_scopes: Vec<String>,
 }
 
 /// Signal channel configuration (signal-cli daemon HTTP/JSON-RPC).
@@ -115,6 +136,118 @@ impl ChannelsConfig {
                 .or_else(|| cs.gateway_user_id.clone())
                 .unwrap_or_else(|| owner_id.to_string());
 
+            let memory_layers: Vec<crate::workspace::layer::MemoryLayer> =
+                match optional_env("MEMORY_LAYERS")? {
+                    Some(json_str) => {
+                        serde_json::from_str(&json_str).map_err(|e| ConfigError::InvalidValue {
+                            key: "MEMORY_LAYERS".to_string(),
+                            message: format!("must be valid JSON array of layer objects: {e}"),
+                        })?
+                    }
+                    None => crate::workspace::layer::MemoryLayer::default_for_user(&user_id),
+                };
+
+            // Validate layer names and scopes
+            for layer in &memory_layers {
+                if layer.name.trim().is_empty() {
+                    return Err(ConfigError::InvalidValue {
+                        key: "MEMORY_LAYERS".to_string(),
+                        message: "layer name must not be empty".to_string(),
+                    });
+                }
+                if layer.name.len() > 64 {
+                    return Err(ConfigError::InvalidValue {
+                        key: "MEMORY_LAYERS".to_string(),
+                        message: format!("layer name '{}' exceeds 64 characters", layer.name),
+                    });
+                }
+                if !layer
+                    .name
+                    .chars()
+                    .all(|c| c.is_ascii_alphanumeric() || c == '_' || c == '-')
+                {
+                    return Err(ConfigError::InvalidValue {
+                        key: "MEMORY_LAYERS".to_string(),
+                        message: format!(
+                            "layer name '{}' contains invalid characters \
+                             (allowed: a-z, A-Z, 0-9, _, -)",
+                            layer.name
+                        ),
+                    });
+                }
+                if layer.scope.trim().is_empty() {
+                    return Err(ConfigError::InvalidValue {
+                        key: "MEMORY_LAYERS".to_string(),
+                        message: format!("layer '{}' has an empty scope", layer.name),
+                    });
+                }
+            }
+
+            // Check for duplicate layer names
+            {
+                let mut seen = std::collections::HashSet::new();
+                for layer in &memory_layers {
+                    if !seen.insert(&layer.name) {
+                        return Err(ConfigError::InvalidValue {
+                            key: "MEMORY_LAYERS".to_string(),
+                            message: format!("duplicate layer name '{}'", layer.name),
+                        });
+                    }
+                }
+            }
+
+            let user_tokens: Option<HashMap<String, UserTokenConfig>> =
+                match optional_env("GATEWAY_USER_TOKENS")? {
+                    Some(json_str) => {
+                        let tokens: HashMap<String, UserTokenConfig> = serde_json::from_str(
+                            &json_str,
+                        )
+                        .map_err(|e| ConfigError::InvalidValue {
+                            key: "GATEWAY_USER_TOKENS".to_string(),
+                            message: format!(
+                                "must be valid JSON object mapping tokens to user configs: {e}"
+                            ),
+                        })?;
+                        if tokens.is_empty() {
+                            return Err(ConfigError::InvalidValue {
+                            key: "GATEWAY_USER_TOKENS".to_string(),
+                            message:
+                                "token map is empty — remove the variable to use single-user mode"
+                                    .to_string(),
+                        });
+                        }
+                        for (tok, cfg) in &tokens {
+                            if cfg.user_id.trim().is_empty() {
+                                return Err(ConfigError::InvalidValue {
+                                    key: "GATEWAY_USER_TOKENS".to_string(),
+                                    message: format!(
+                                        "token '{}...' has an empty user_id",
+                                        &tok[..tok.len().min(8)]
+                                    ),
+                                });
+                            }
+                        }
+                        Some(tokens)
+                    }
+                    None => None,
+                };
+            let workspace_read_scopes: Vec<String> = optional_env("WORKSPACE_READ_SCOPES")?
+                .map(|s| {
+                    s.split(',')
+                        .map(|s| s.trim().to_string())
+                        .filter(|s| !s.is_empty())
+                        .collect()
+                })
+                .unwrap_or_default();
+
+            for scope in &workspace_read_scopes {
+                if scope.len() > 128 {
+                    return Err(ConfigError::InvalidValue {
+                        key: "WORKSPACE_READ_SCOPES".to_string(),
+                        message: format!("scope '{}...' exceeds 128 characters", &scope[..32]),
+                    });
+                }
+            }
             Some(GatewayConfig {
                 host: optional_env("GATEWAY_HOST")?
                     .or_else(|| cs.gateway_host.clone())
@@ -126,6 +259,9 @@ impl ChannelsConfig {
                 auth_token: optional_env("GATEWAY_AUTH_TOKEN")?
                     .or_else(|| cs.gateway_auth_token.clone()),
                 user_id,
+                workspace_read_scopes,
+                memory_layers,
+                user_tokens,
             })
         } else {
             None
@@ -281,6 +417,9 @@ mod tests {
             port: 3000,
             auth_token: Some("tok-abc".to_string()),
             user_id: "default".to_string(),
+            workspace_read_scopes: vec![],
+            memory_layers: vec![],
+            user_tokens: None,
         };
         assert_eq!(cfg.host, "127.0.0.1");
         assert_eq!(cfg.port, 3000);
@@ -295,6 +434,9 @@ mod tests {
             port: 3001,
             auth_token: None,
             user_id: "anon".to_string(),
+            workspace_read_scopes: vec![],
+            memory_layers: vec![],
+            user_tokens: None,
         };
         assert!(cfg.auth_token.is_none());
     }

src/config/llm.rs

@@ -406,7 +406,7 @@ impl LlmConfig {
         // Resolve extra headers
         let extra_headers = if let Some(env_var) = extra_headers_env {
             optional_env(env_var)?
-                .map(|val| parse_extra_headers(&val))
+                .map(|val| parse_extra_headers_with_key(&val, env_var))
                 .transpose()?
                 .unwrap_or_default()
         } else {
@@ -475,7 +475,10 @@ impl LlmConfig {
 ///
 /// Format: `Key1:Value1,Key2:Value2` (colon-separated, not `=`, because
 /// header values often contain `=`).
-fn parse_extra_headers(val: &str) -> Result<Vec<(String, String)>, ConfigError> {
+fn parse_extra_headers_with_key(
+    val: &str,
+    env_var_name: &str,
+) -> Result<Vec<(String, String)>, ConfigError> {
     if val.trim().is_empty() {
         return Ok(Vec::new());
     }
@@ -488,14 +491,14 @@ fn parse_extra_headers(val: &str) -> Result<Vec<(String, String)>, ConfigError>
         }
         let Some((key, value)) = pair.split_once(':') else {
             return Err(ConfigError::InvalidValue {
-                key: "LLM_EXTRA_HEADERS".to_string(),
+                key: env_var_name.to_string(),
                 message: format!("malformed header entry '{}', expected Key:Value", pair),
             });
         };
         let key = key.trim();
         if key.is_empty() {
             return Err(ConfigError::InvalidValue {
-                key: "LLM_EXTRA_HEADERS".to_string(),
+                key: env_var_name.to_string(),
                 message: format!("empty header name in entry '{}'", pair),
             });
         }
@@ -536,6 +539,11 @@ mod tests {
     use crate::settings::Settings;
     use crate::testing::credentials::*;
 
+    /// Convenience wrapper for tests — uses "TEST_HEADERS" as the env var name.
+    fn parse_extra_headers(val: &str) -> Result<Vec<(String, String)>, ConfigError> {
+        parse_extra_headers_with_key(val, "TEST_HEADERS")
+    }
+
     /// Clear all openai-compatible-related env vars.
     fn clear_openai_compatible_env() {
         // SAFETY: Only called under ENV_MUTEX in tests.

src/config/mod.rs

@@ -312,13 +312,11 @@ impl Config {
         let tunnel = TunnelConfig::resolve(settings)?;
         let channels = ChannelsConfig::resolve(settings, &owner_id)?;
 
-        // Resolve workspace config using the gateway user_id for default layers.
-        let workspace_user_id = channels
-            .gateway
-            .as_ref()
-            .map(|gw| gw.user_id.as_str())
-            .unwrap_or("default");
-        let workspace = WorkspaceConfig::resolve(workspace_user_id)?;
+        // Resolve the startup workspace against the durable owner scope. The
+        // gateway may expose a distinct sender identity, but the base runtime
+        // workspace stays owner-scoped and per-user gateway workspaces are
+        // handled separately by WorkspacePool.
+        let workspace = WorkspaceConfig::resolve(&owner_id)?;
 
         Ok(Self {
             owner_id: owner_id.clone(),

src/db/libsql/jobs.rs

@@ -230,6 +230,49 @@ impl JobStore for LibSqlBackend {
         Ok(jobs)
     }
 
+    async fn list_agent_jobs_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<Vec<AgentJobRecord>, DatabaseError> {
+        let conn = self.connect().await?;
+        let mut rows = conn
+            .query(
+                r#"
+                SELECT id, title, status, user_id, failure_reason,
+                       created_at, started_at, completed_at
+                FROM agent_jobs WHERE source = 'direct' AND user_id = ?1
+                ORDER BY created_at DESC
+                "#,
+                params![user_id],
+            )
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+
+        let mut jobs = Vec::new();
+        while let Some(row) = rows
+            .next()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        {
+            let id_str = get_text(&row, 0);
+            let Ok(id) = id_str.parse() else {
+                tracing::warn!("Skipping agent job with invalid UUID: {}", id_str);
+                continue;
+            };
+            jobs.push(AgentJobRecord {
+                id,
+                title: get_text(&row, 1),
+                status: get_text(&row, 2),
+                user_id: get_text(&row, 3),
+                failure_reason: get_opt_text(&row, 4),
+                created_at: get_ts(&row, 5),
+                started_at: get_opt_ts(&row, 6),
+                completed_at: get_opt_ts(&row, 7),
+            });
+        }
+        Ok(jobs)
+    }
+
     async fn get_agent_job_failure_reason(
         &self,
         id: Uuid,
@@ -277,6 +320,32 @@ impl JobStore for LibSqlBackend {
         Ok(summary)
     }
 
+    async fn agent_job_summary_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<AgentJobSummary, DatabaseError> {
+        let conn = self.connect().await?;
+        let mut rows = conn
+            .query(
+                "SELECT status, COUNT(*) as cnt FROM agent_jobs WHERE source = 'direct' AND user_id = ?1 GROUP BY status",
+                params![user_id],
+            )
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+
+        let mut summary = AgentJobSummary::default();
+        while let Some(row) = rows
+            .next()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        {
+            let status = get_text(&row, 0);
+            let count = get_i64(&row, 1) as usize;
+            summary.add_count(&status, count);
+        }
+        Ok(summary)
+    }
+
     async fn save_action(&self, job_id: Uuid, action: &ActionRecord) -> Result<(), DatabaseError> {
         let conn = self.connect().await?;
         let duration_ms = action.duration.as_millis() as i64;

src/db/libsql/routines.rs

@@ -462,6 +462,56 @@ impl RoutineStore for LibSqlBackend {
         Ok(counts)
     }
 
+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError> {
+        if routine_ids.is_empty() {
+            return Ok(HashMap::new());
+        }
+
+        let conn = self.connect().await?;
+
+        // SQLite doesn't support ANY($1), so we query all latest runs and filter in memory.
+        // Uses a subquery to pick only the most recent run per routine.
+        let mut rows = conn
+            .query(
+                "SELECT routine_id, status FROM routine_runs r1
+                 WHERE started_at = (
+                     SELECT MAX(started_at) FROM routine_runs r2
+                     WHERE r2.routine_id = r1.routine_id
+                 )
+                 GROUP BY routine_id",
+                params![],
+            )
+            .await
+            .map_err(|e| {
+                DatabaseError::Query(format!("Failed to batch get last run status: {}", e))
+            })?;
+
+        let routine_id_set: HashSet<Uuid> = routine_ids.iter().copied().collect();
+        let mut statuses = HashMap::new();
+
+        while let Some(row) = rows
+            .next()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        {
+            let id_str: String = get_text(&row, 0);
+            let id = Uuid::parse_str(&id_str)
+                .map_err(|e| DatabaseError::Query(format!("Invalid routine UUID: {}", e)))?;
+
+            if routine_id_set.contains(&id) {
+                let status_str: String = get_text(&row, 1);
+                if let std::result::Result::Ok(status) = status_str.parse::<RunStatus>() {
+                    statuses.insert(id, status);
+                }
+            }
+        }
+
+        Ok(statuses)
+    }
+
     async fn link_routine_run_to_job(
         &self,
         run_id: Uuid,

src/db/mod.rs

@@ -409,7 +409,15 @@ pub trait JobStore: Send + Sync {
     async fn mark_job_stuck(&self, id: Uuid) -> Result<(), DatabaseError>;
     async fn get_stuck_jobs(&self) -> Result<Vec<Uuid>, DatabaseError>;
     async fn list_agent_jobs(&self) -> Result<Vec<AgentJobRecord>, DatabaseError>;
+    async fn list_agent_jobs_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<Vec<AgentJobRecord>, DatabaseError>;
     async fn agent_job_summary(&self) -> Result<AgentJobSummary, DatabaseError>;
+    async fn agent_job_summary_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<AgentJobSummary, DatabaseError>;
     /// Get the failure reason for a single agent job (O(1) lookup).
     async fn get_agent_job_failure_reason(&self, id: Uuid)
     -> Result<Option<String>, DatabaseError>;
@@ -520,6 +528,15 @@ pub trait RoutineStore: Send + Sync {
         &self,
         routine_ids: &[Uuid],
     ) -> Result<HashMap<Uuid, i64>, DatabaseError>;
+
+    /// Fetch the last run status for multiple routines in a single query.
+    /// Returns a map from routine_id to its most recent RunStatus.
+    /// Routines with no runs are omitted from the result.
+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError>;
+
     async fn link_routine_run_to_job(
         &self,
         run_id: Uuid,

src/db/postgres.rs

@@ -249,10 +249,24 @@ impl JobStore for PgBackend {
         self.store.list_agent_jobs().await
     }
 
+    async fn list_agent_jobs_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<Vec<AgentJobRecord>, DatabaseError> {
+        self.store.list_agent_jobs_for_user(user_id).await
+    }
+
     async fn agent_job_summary(&self) -> Result<AgentJobSummary, DatabaseError> {
         self.store.agent_job_summary().await
     }
 
+    async fn agent_job_summary_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<AgentJobSummary, DatabaseError> {
+        self.store.agent_job_summary_for_user(user_id).await
+    }
+
     async fn get_agent_job_failure_reason(
         &self,
         id: Uuid,
@@ -496,6 +510,14 @@ impl RoutineStore for PgBackend {
             .await
     }
 
+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<std::collections::HashMap<Uuid, crate::agent::routine::RunStatus>, DatabaseError>
+    {
+        self.store.batch_get_last_run_status(routine_ids).await
+    }
+
     async fn link_routine_run_to_job(
         &self,
         run_id: Uuid,

src/history/store.rs

@@ -842,6 +842,38 @@ impl Store {
             .collect())
     }
 
+    pub async fn list_agent_jobs_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<Vec<AgentJobRecord>, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = conn
+            .query(
+                r#"
+                SELECT id, title, status, user_id, failure_reason,
+                       created_at, started_at, completed_at
+                FROM agent_jobs WHERE source = 'direct' AND user_id = $1
+                ORDER BY created_at DESC
+                "#,
+                &[&user_id],
+            )
+            .await?;
+
+        Ok(rows
+            .iter()
+            .map(|r| AgentJobRecord {
+                id: r.get("id"),
+                title: r.get("title"),
+                status: r.get("status"),
+                user_id: r.get::<_, Option<String>>("user_id").unwrap_or_default(),
+                created_at: r.get("created_at"),
+                started_at: r.get("started_at"),
+                completed_at: r.get("completed_at"),
+                failure_reason: r.get("failure_reason"),
+            })
+            .collect())
+    }
+
     /// Get the failure reason for a single agent job.
     pub async fn get_agent_job_failure_reason(
         &self,
@@ -875,6 +907,27 @@ impl Store {
         }
         Ok(summary)
     }
+
+    pub async fn agent_job_summary_for_user(
+        &self,
+        user_id: &str,
+    ) -> Result<AgentJobSummary, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = conn
+            .query(
+                "SELECT status, COUNT(*) as cnt FROM agent_jobs WHERE source = 'direct' AND user_id = $1 GROUP BY status",
+                &[&user_id],
+            )
+            .await?;
+
+        let mut summary = AgentJobSummary::default();
+        for row in &rows {
+            let status: String = row.get("status");
+            let count: i64 = row.get("cnt");
+            summary.add_count(&status, count as usize);
+        }
+        Ok(summary)
+    }
 }
 
 // ==================== Job Events ====================
@@ -1350,6 +1403,40 @@ impl Store {
         Ok(counts)
     }
 
+    /// Batch-load the most recent run status for multiple routines in a single query.
+    /// Uses a window function to pick only the latest run per routine.
+    #[cfg(feature = "postgres")]
+    pub async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError> {
+        if routine_ids.is_empty() {
+            return Ok(HashMap::new());
+        }
+
+        let conn = self.conn().await?;
+        let rows = conn
+            .query(
+                "SELECT DISTINCT ON (routine_id) routine_id, status
+                 FROM routine_runs
+                 WHERE routine_id = ANY($1)
+                 ORDER BY routine_id, started_at DESC",
+                &[&routine_ids],
+            )
+            .await?;
+
+        let mut statuses = HashMap::new();
+        for row in rows {
+            let id: Uuid = row.get("routine_id");
+            let status_str: String = row.get("status");
+            if let std::result::Result::Ok(status) = status_str.parse::<RunStatus>() {
+                statuses.insert(id, status);
+            }
+        }
+
+        Ok(statuses)
+    }
+
     /// Link a routine run to a dispatched job.
     pub async fn link_routine_run_to_job(
         &self,

src/llm/github_copilot.rs

@@ -107,14 +107,21 @@ impl GithubCopilotProvider {
         body: &impl Serialize,
     ) -> Result<R, LlmError> {
         let url = self.api_url();
-        // Map token exchange failures to RequestFailed (retryable) rather than
-        // AuthFailed (non-retryable), since transient network errors during
-        // exchange should be retried by RetryProvider.
+        // Distinguish permanent auth errors (non-retryable) from transient
+        // network failures (retryable) so RetryProvider handles them correctly.
         let token = self.token_manager.get_token().await.map_err(|e| {
             tracing::warn!(error = %e, "Copilot: token exchange failed");
-            LlmError::RequestFailed {
-                provider: "github_copilot".to_string(),
-                reason: format!("Token exchange failed: {e}"),
+            match &e {
+                crate::llm::github_copilot_auth::GithubCopilotAuthError::AccessDenied
+                | crate::llm::github_copilot_auth::GithubCopilotAuthError::Expired => {
+                    LlmError::AuthFailed {
+                        provider: "github_copilot".to_string(),
+                    }
+                }
+                _ => LlmError::RequestFailed {
+                    provider: "github_copilot".to_string(),
+                    reason: format!("Token exchange failed: {e}"),
+                },
             }
         })?;
 
@@ -157,54 +164,14 @@ impl GithubCopilotProvider {
             );
 
             if status.as_u16() == 401 {
-                // Invalidate the cached session token and retry once with a
-                // fresh exchange — stale tokens are the most common 401 cause.
-                tracing::warn!("Copilot: 401 Unauthorized — invalidating session token, retrying");
+                // Invalidate the cached session token so the next attempt
+                // (driven by RetryProvider) gets a fresh one. We don't retry
+                // inline to avoid nested retries with the outer RetryProvider.
+                tracing::warn!("Copilot: 401 Unauthorized — invalidating session token for retry");
                 self.token_manager.invalidate().await;
-                let fresh = self.token_manager.get_token().await.map_err(|e| {
-                    tracing::warn!(error = %e, "Copilot: re-exchange after 401 failed");
-                    LlmError::RequestFailed {
-                        provider: "github_copilot".to_string(),
-                        reason: format!("Token re-exchange after 401 failed: {e}"),
-                    }
-                })?;
-                let mut retry_req = self
-                    .client
-                    .post(&url)
-                    .bearer_auth(fresh.expose_secret())
-                    .header("Content-Type", "application/json");
-                for (key, value) in &self.extra_headers {
-                    retry_req = retry_req.header(key.as_str(), value.as_str());
-                }
-                let retry =
-                    retry_req
-                        .json(body)
-                        .send()
-                        .await
-                        .map_err(|e| LlmError::RequestFailed {
-                            provider: "github_copilot".to_string(),
-                            reason: format!("Retry after 401 failed: {e}"),
-                        })?;
-                if retry.status().is_success() {
-                    let text = retry.text().await.map_err(|e| LlmError::RequestFailed {
-                        provider: "github_copilot".to_string(),
-                        reason: format!("Failed to read retry response body: {e}"),
-                    })?;
-                    return serde_json::from_str(&text).map_err(|e| {
-                        let truncated = crate::agent::truncate_for_preview(&text, 512);
-                        LlmError::InvalidResponse {
-                            provider: "github_copilot".to_string(),
-                            reason: format!("JSON parse error: {e}. Raw: {truncated}"),
-                        }
-                    });
-                }
-                let retry_status = retry.status();
-                tracing::warn!(
-                    status = %retry_status,
-                    "Copilot: 401 retry also failed"
-                );
-                return Err(LlmError::AuthFailed {
+                return Err(LlmError::RequestFailed {
                     provider: "github_copilot".to_string(),
+                    reason: "HTTP 401 Unauthorized".to_string(),
                 });
             }
             if status.as_u16() == 429 {

src/main.rs

@@ -589,15 +589,47 @@ async fn async_main() -> anyhow::Result<()> {
     // ── Gateway channel ────────────────────────────────────────────────
 
     let mut gateway_url: Option<String> = None;
-    let mut sse_sender: Option<
-        tokio::sync::broadcast::Sender<ironclaw::channels::web::types::SseEvent>,
-    > = None;
+    let mut sse_manager: Option<std::sync::Arc<ironclaw::channels::web::sse::SseManager>> = None;
     if let Some(ref gw_config) = config.channels.gateway {
-        let mut gw =
-            GatewayChannel::new(gw_config.clone()).with_llm_provider(Arc::clone(&components.llm));
+        // Build multi-user auth state if user_tokens is configured, else single-user.
+        let mut gw = if let Some(ref user_tokens) = gw_config.user_tokens {
+            use ironclaw::channels::web::auth::{MultiAuthState, UserIdentity};
+            let tokens = user_tokens
+                .iter()
+                .map(|(token, cfg)| {
+                    (
+                        token.clone(),
+                        UserIdentity {
+                            user_id: cfg.user_id.clone(),
+                            workspace_read_scopes: cfg.workspace_read_scopes.clone(),
+                        },
+                    )
+                })
+                .collect();
+            let auth = MultiAuthState::multi(tokens);
+            GatewayChannel::new_multi_auth(gw_config.clone(), auth)
+        } else {
+            GatewayChannel::new(gw_config.clone())
+        };
+        gw = gw.with_owner_scope(config.owner_id.clone());
+        gw = gw.with_llm_provider(Arc::clone(&components.llm));
         if let Some(ref ws) = components.workspace {
             gw = gw.with_workspace(Arc::clone(ws));
         }
+        // Create per-user workspace pool for multi-user mode.
+        if let Some(ref db) = components.db {
+            let emb_cache_config = ironclaw::workspace::EmbeddingCacheConfig {
+                max_entries: config.embeddings.cache_size,
+            };
+            let pool = Arc::new(ironclaw::channels::web::server::WorkspacePool::new(
+                Arc::clone(db),
+                components.embeddings.clone(),
+                emb_cache_config,
+                config.search.clone(),
+                config.workspace.clone(),
+            ));
+            gw = gw.with_workspace_pool(pool);
+        }
         gw = gw.with_session_manager(Arc::clone(&session_manager));
         gw = gw.with_log_broadcaster(Arc::clone(&log_broadcaster));
         gw = gw.with_log_level_handle(Arc::clone(&log_level_handle));
@@ -648,8 +680,12 @@ async fn async_main() -> anyhow::Result<()> {
                 let mut rx = tx.subscribe();
                 let gw_state = Arc::clone(gw.state());
                 tokio::spawn(async move {
-                    while let Ok((_job_id, event)) = rx.recv().await {
-                        gw_state.sse.broadcast(event);
+                    while let Ok((_job_id, user_id, event)) = rx.recv().await {
+                        if user_id.is_empty() {
+                            gw_state.sse.broadcast(event);
+                        } else {
+                            gw_state.sse.broadcast_for_user(&user_id, event);
+                        }
                     }
                 });
             }
@@ -691,7 +727,7 @@ async fn async_main() -> anyhow::Result<()> {
         // Capture SSE sender and routine engine slot before moving gw into channels.
         // IMPORTANT: This must come after all `with_*` calls since `rebuild_state`
         // creates a new SseManager, which would orphan this sender.
-        sse_sender = Some(gw.state().sse.sender());
+        sse_manager = Some(Arc::clone(&gw.state().sse));
         channel_names.push("gateway".to_string());
         channels.add(Box::new(gw)).await;
     }
@@ -754,6 +790,14 @@ async fn async_main() -> anyhow::Result<()> {
         .register_message_tools(Arc::clone(&channels), components.extension_manager.clone())
         .await;
 
+    // Default user ID for extension operations (single-user mode).
+    let ext_user_id = config
+        .channels
+        .gateway
+        .as_ref()
+        .map(|g| g.user_id.clone())
+        .unwrap_or_else(|| "default".to_string());
+
     // Wire up channel runtime for hot-activation of WASM channels.
     if let Some(ref ext_mgr) = components.extension_manager
         && let Some((rt, ps, router)) = wasm_channel_runtime_state.take()
@@ -774,12 +818,14 @@ async fn async_main() -> anyhow::Result<()> {
 
         // Auto-activate WASM channels that were active in a previous session.
         // Relay channels are handled separately below via restore_relay_channels().
-        let persisted = ext_mgr.load_persisted_active_channels().await;
+        let persisted = ext_mgr.load_persisted_active_channels(&ext_user_id).await;
         for name in &persisted {
-            if active_at_startup.contains(name) || ext_mgr.is_relay_channel(name).await {
+            if active_at_startup.contains(name)
+                || ext_mgr.is_relay_channel(name, &ext_user_id).await
+            {
                 continue;
             }
-            match ext_mgr.activate(name).await {
+            match ext_mgr.activate(name, &ext_user_id).await {
                 Ok(result) => {
                     tracing::debug!(
                         channel = %name,
@@ -804,14 +850,14 @@ async fn async_main() -> anyhow::Result<()> {
         ext_mgr
             .set_relay_channel_manager(Arc::clone(&channels))
             .await;
-        ext_mgr.restore_relay_channels().await;
+        ext_mgr.restore_relay_channels(&ext_user_id).await;
     }
 
     // Wire SSE sender into extension manager for broadcasting status events.
     if let Some(ref ext_mgr) = components.extension_manager
-        && let Some(ref sender) = sse_sender
+        && let Some(ref sse) = sse_manager
     {
-        ext_mgr.set_sse_sender(sender.clone()).await;
+        ext_mgr.set_sse_sender(Arc::clone(sse)).await;
     }
 
     // Snapshot memory for trace recording before the agent starts
@@ -849,7 +895,7 @@ async fn async_main() -> anyhow::Result<()> {
         skills_config: config.skills.clone(),
         hooks: components.hooks,
         cost_guard: components.cost_guard,
-        sse_tx: sse_sender,
+        sse_tx: sse_manager,
         http_interceptor,
         transcription: config.transcription.create_provider().map(|p| {
             Arc::new(ironclaw::llm::transcription::TranscriptionMiddleware::new(
@@ -867,6 +913,7 @@ async fn async_main() -> anyhow::Result<()> {
             ironclaw::agent::routine_engine::SandboxReadiness::DockerUnavailable
         },
         builder: components.builder,
+        llm_backend: config.llm.backend.clone(),
     };
 
     let channels_for_warnings = Arc::clone(&channels);

src/orchestrator/api.rs

@@ -40,7 +40,8 @@ pub struct OrchestratorState {
     pub job_manager: Arc<ContainerJobManager>,
     pub token_store: TokenStore,
     /// Broadcast channel for job events (consumed by the web gateway SSE).
-    pub job_event_tx: Option<broadcast::Sender<(Uuid, SseEvent)>>,
+    /// Tuple: (job_id, user_id, event).
+    pub job_event_tx: Option<broadcast::Sender<(Uuid, String, SseEvent)>>,
     /// Buffered follow-up prompts for sandbox jobs, keyed by job_id.
     pub prompt_queue: Arc<Mutex<HashMap<Uuid, VecDeque<PendingPrompt>>>>,
     /// Database handle for persisting job events.
@@ -49,6 +50,9 @@ pub struct OrchestratorState {
     pub secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>>,
     /// User ID for secret lookups (single-tenant, typically "default").
     pub user_id: String,
+    /// In-memory cache of job_id → user_id for SSE scoping. Populated when
+    /// sandbox jobs are created, avoiding a DB round-trip on every job event.
+    pub job_owner_cache: Arc<std::sync::RwLock<HashMap<Uuid, String>>>,
 }
 
 /// The orchestrator's internal API server.
@@ -351,9 +355,45 @@ async fn job_event_handler(
         },
     };
 
-    // Broadcast via the channel (if configured)
+    // Broadcast via the channel (if configured).
+    // Look up the job owner from the in-memory cache (populated at job creation).
     if let Some(ref tx) = state.job_event_tx {
-        let _ = tx.send((job_id, sse_event));
+        let cached_uid = state
+            .job_owner_cache
+            .read()
+            .unwrap_or_else(|e| e.into_inner())
+            .get(&job_id)
+            .cloned();
+
+        let user_id = match cached_uid {
+            Some(uid) => uid,
+            None => {
+                // Cache miss: fall back to DB lookup and populate cache.
+                let uid = match state.store.as_ref() {
+                    Some(store) => store
+                        .get_sandbox_job(job_id)
+                        .await
+                        .ok()
+                        .flatten()
+                        .map(|j| j.user_id),
+                    None => None,
+                };
+                if let Some(ref uid) = uid {
+                    state
+                        .job_owner_cache
+                        .write()
+                        .unwrap_or_else(|e| e.into_inner())
+                        .insert(job_id, uid.clone());
+                }
+                uid.unwrap_or_default()
+            }
+        };
+
+        if user_id.is_empty() {
+            let _ = tx.send((job_id, String::new(), sse_event));
+        } else {
+            let _ = tx.send((job_id, user_id, sse_event));
+        }
     }
 
     Ok(StatusCode::OK)
@@ -480,6 +520,7 @@ mod tests {
             store: None,
             secrets_store: None,
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(HashMap::new())),
         }
     }
 
@@ -709,6 +750,7 @@ mod tests {
             store: None,
             secrets_store: Some(secrets_store),
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(HashMap::new())),
         };
 
         let router = OrchestratorApi::router(state);
@@ -744,6 +786,7 @@ mod tests {
             store: None,
             secrets_store: None,
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(HashMap::new())),
         };
 
         let job_id = Uuid::new_v4();
@@ -769,8 +812,10 @@ mod tests {
         let resp = router.oneshot(req).await.unwrap();
         assert_eq!(resp.status(), StatusCode::OK);
 
-        let (recv_id, event) = rx.recv().await.unwrap();
+        let (recv_id, recv_uid, event) = rx.recv().await.unwrap();
         assert_eq!(recv_id, job_id);
+        // No store configured, so user_id falls back to empty string.
+        assert_eq!(recv_uid, "");
         match event {
             SseEvent::JobMessage {
                 job_id: jid,
@@ -799,6 +844,7 @@ mod tests {
             store: None,
             secrets_store: None,
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(HashMap::new())),
         };
 
         let job_id = Uuid::new_v4();
@@ -824,7 +870,7 @@ mod tests {
         let resp = router.oneshot(req).await.unwrap();
         assert_eq!(resp.status(), StatusCode::OK);
 
-        let (_recv_id, event) = rx.recv().await.unwrap();
+        let (_recv_id, _recv_uid, event) = rx.recv().await.unwrap();
         match event {
             SseEvent::JobToolUse { tool_name, .. } => {
                 assert_eq!(tool_name, "shell");
@@ -847,6 +893,7 @@ mod tests {
             store: None,
             secrets_store: None,
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(HashMap::new())),
         };
 
         let job_id = Uuid::new_v4();
@@ -869,7 +916,7 @@ mod tests {
         let resp = router.oneshot(req).await.unwrap();
         assert_eq!(resp.status(), StatusCode::OK);
 
-        let (_recv_id, event) = rx.recv().await.unwrap();
+        let (_recv_id, _recv_uid, event) = rx.recv().await.unwrap();
         // Unknown event types fall through to JobStatus
         assert!(matches!(event, SseEvent::JobStatus { .. }));
     }

src/orchestrator/mod.rs

@@ -63,7 +63,7 @@ fn resolve_orchestrator_port() -> u16 {
 /// Result of orchestrator setup, containing all handles needed by the agent.
 pub struct OrchestratorSetup {
     pub container_job_manager: Option<Arc<ContainerJobManager>>,
-    pub job_event_tx: Option<broadcast::Sender<(Uuid, SseEvent)>>,
+    pub job_event_tx: Option<broadcast::Sender<(Uuid, String, SseEvent)>>,
     pub prompt_queue: Arc<Mutex<HashMap<Uuid, VecDeque<api::PendingPrompt>>>>,
     pub docker_status: crate::sandbox::DockerStatus,
 }
@@ -134,6 +134,7 @@ pub async fn setup_orchestrator(
             store: db.cloned(),
             secrets_store: secrets_store.cloned(),
             user_id: "default".to_string(),
+            job_owner_cache: Arc::new(std::sync::RwLock::new(std::collections::HashMap::new())),
         };
 
         tokio::spawn(async move {

src/settings.rs

@@ -1297,6 +1297,92 @@ mod tests {
         assert_eq!(loaded.heartbeat.interval_secs, 900);
     }
 
+    /// Regression: /model writes a single key ("selected_model") to the DB via
+    /// set_setting(). On restart, get_all_settings() returns ALL keys including
+    /// wizard-written defaults. The single-key update must survive the full
+    /// from_db_map() round trip.
+    #[test]
+    fn db_single_key_model_update_survives_roundtrip() {
+        // Step 1: Wizard writes full settings to DB (including selected_model
+        // from initial setup).
+        let wizard_settings = Settings {
+            llm_backend: Some("nearai".to_string()),
+            selected_model: Some("old-wizard-model".to_string()),
+            ..Default::default()
+        };
+        let mut db: std::collections::HashMap<String, serde_json::Value> =
+            wizard_settings.to_db_map();
+
+        // Step 2: User runs /model new-model — persist_selected_model writes
+        // a single key, overwriting the wizard value.
+        db.insert(
+            "selected_model".to_string(),
+            serde_json::Value::String("new-model".to_string()),
+        );
+
+        // Step 3: On restart, from_db_map() rebuilds Settings from the full
+        // DB map.
+        let restored = Settings::from_db_map(&db);
+        assert_eq!(
+            restored.selected_model,
+            Some("new-model".to_string()),
+            "/model change must survive DB round trip"
+        );
+    }
+
+    /// Regression: TOML overlay must not clobber a DB-persisted selected_model
+    /// when the TOML file matches the DB. This is the normal case after /model
+    /// successfully writes to both DB and TOML.
+    #[test]
+    fn toml_overlay_preserves_matching_model() {
+        // DB settings with new model from /model command.
+        let mut db_settings = Settings {
+            llm_backend: Some("nearai".to_string()),
+            selected_model: Some("new-model".to_string()),
+            ..Default::default()
+        };
+
+        // TOML also updated by /model command to the same value.
+        let toml_settings = Settings {
+            selected_model: Some("new-model".to_string()),
+            ..Default::default()
+        };
+
+        db_settings.merge_from(&toml_settings);
+        assert_eq!(
+            db_settings.selected_model,
+            Some("new-model".to_string()),
+            "TOML overlay must not clobber matching model"
+        );
+    }
+
+    /// Regression: when /model updates DB but TOML write fails, a stale TOML
+    /// file would overwrite the DB value. This test documents the priority:
+    /// TOML > DB (by design). persist_selected_model MUST update the TOML.
+    #[test]
+    fn stale_toml_overwrites_db_model() {
+        // DB has the new model from /model.
+        let mut db_settings = Settings {
+            selected_model: Some("new-model".to_string()),
+            ..Default::default()
+        };
+
+        // TOML still has the old model (write failed or was not attempted).
+        let stale_toml = Settings {
+            selected_model: Some("old-model".to_string()),
+            ..Default::default()
+        };
+
+        db_settings.merge_from(&stale_toml);
+        // This documents the current priority: TOML wins over DB.
+        // The fix in persist_selected_model ensures TOML is always updated.
+        assert_eq!(
+            db_settings.selected_model,
+            Some("old-model".to_string()),
+            "TOML overlay has higher priority than DB (by design)"
+        );
+    }
+
     /// Regression test: /model command must persist selected_model to TOML config.
     /// Prior to the fix, `set_model()` only changed the in-memory provider and the
     /// choice was lost on restart.
@@ -1322,6 +1408,28 @@ mod tests {
         assert_eq!(reloaded.selected_model, Some("new-model".to_string()));
     }
 
+    /// Regression: /model must create config.toml when it doesn't exist, so the
+    /// model survives restarts. Previously the Ok(None) case was a no-op.
+    #[test]
+    fn toml_created_when_missing_for_model_persist() {
+        let dir = tempfile::tempdir().unwrap();
+        let path = dir.path().join("config.toml");
+
+        // No config.toml yet (fresh install, no wizard).
+        assert!(Settings::load_toml(&path).unwrap().is_none());
+
+        // Simulate what persist_selected_model now does for the Ok(None) case.
+        let settings = Settings {
+            selected_model: Some("new-model".to_string()),
+            ..Default::default()
+        };
+        settings.save_toml(&path).unwrap();
+
+        // Verify the model survived.
+        let loaded = Settings::load_toml(&path).unwrap().unwrap();
+        assert_eq!(loaded.selected_model, Some("new-model".to_string()));
+    }
+
     #[test]
     fn toml_missing_file_returns_none() {
         let result = Settings::load_toml(std::path::Path::new("/tmp/nonexistent_config.toml"));

src/testing/mod.rs

@@ -563,6 +563,7 @@ impl TestHarnessBuilder {
             document_extraction: None,
             sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
+            llm_backend: "nearai".to_string(),
         };
 
         TestHarness {

src/tools/builtin/extension_tools.rs

@@ -130,7 +130,7 @@ impl Tool for ToolInstallTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -150,7 +150,7 @@ impl Tool for ToolInstallTool {
 
         let result = self
             .manager
-            .install(name, url, kind_hint)
+            .install(name, url, kind_hint, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
@@ -205,7 +205,7 @@ impl Tool for ToolAuthTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -213,13 +213,13 @@ impl Tool for ToolAuthTool {
 
         let result = self
             .manager
-            .auth(name)
+            .auth(name, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
         // Auto-activate after successful auth so tools are available immediately
         if result.is_authenticated() {
-            match self.manager.activate(name).await {
+            match self.manager.activate(name, &ctx.user_id).await {
                 Ok(activate_result) => {
                     let output = serde_json::json!({
                         "status": "authenticated_and_activated",
@@ -304,13 +304,13 @@ impl Tool for ToolActivateTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
         let name = require_str(&params, "name")?;
 
-        match self.manager.activate(name).await {
+        match self.manager.activate(name, &ctx.user_id).await {
             Ok(result) => {
                 let output = serde_json::to_value(&result)
                     .unwrap_or_else(|_| serde_json::json!({"error": "serialization failed"}));
@@ -329,12 +329,12 @@ impl Tool for ToolActivateTool {
 
                 // Activation failed due to missing auth; initiate auth flow
                 // so the agent loop can show the auth card.
-                match self.manager.auth(name).await {
+                match self.manager.auth(name, &ctx.user_id).await {
                     Ok(auth_result) if auth_result.is_authenticated() => {
                         // Auth succeeded (e.g. env var was set); retry activation.
                         let result = self
                             .manager
-                            .activate(name)
+                            .activate(name, &ctx.user_id)
                             .await
                             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
                         let output = serde_json::to_value(&result).unwrap_or_else(
@@ -404,7 +404,7 @@ impl Tool for ToolListTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -425,7 +425,7 @@ impl Tool for ToolListTool {
 
         let extensions = self
             .manager
-            .list(kind_filter, include_available)
+            .list(kind_filter, include_available, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
@@ -477,7 +477,7 @@ impl Tool for ToolRemoveTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -485,7 +485,7 @@ impl Tool for ToolRemoveTool {
 
         let message = self
             .manager
-            .remove(name)
+            .remove(name, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
@@ -541,7 +541,7 @@ impl Tool for ToolUpgradeTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -549,7 +549,7 @@ impl Tool for ToolUpgradeTool {
 
         let result = self
             .manager
-            .upgrade(name)
+            .upgrade(name, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
@@ -603,7 +603,7 @@ impl Tool for ExtensionInfoTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -611,7 +611,7 @@ impl Tool for ExtensionInfoTool {
 
         let info = self
             .manager
-            .extension_info(name)
+            .extension_info(name, &ctx.user_id)
             .await
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 

src/tools/builtin/job.rs

@@ -85,7 +85,7 @@ pub struct CreateJobTool {
     job_manager: Option<Arc<ContainerJobManager>>,
     store: Option<Arc<dyn Database>>,
     /// Broadcast sender for job events (used to subscribe a monitor).
-    event_tx: Option<tokio::sync::broadcast::Sender<(Uuid, SseEvent)>>,
+    event_tx: Option<tokio::sync::broadcast::Sender<(Uuid, String, SseEvent)>>,
     /// Injection channel for pushing messages into the agent loop.
     inject_tx: Option<tokio::sync::mpsc::Sender<IncomingMessage>>,
     /// Encrypted secrets store for validating credential grants.
@@ -120,7 +120,7 @@ impl CreateJobTool {
     /// monitor that forwards Claude Code output to the main agent loop.
     pub fn with_monitor_deps(
         mut self,
-        event_tx: tokio::sync::broadcast::Sender<(Uuid, SseEvent)>,
+        event_tx: tokio::sync::broadcast::Sender<(Uuid, String, SseEvent)>,
         inject_tx: tokio::sync::mpsc::Sender<IncomingMessage>,
     ) -> Self {
         self.event_tx = Some(event_tx);

src/tools/builtin/memory.rs

@@ -21,6 +21,35 @@ use crate::context::JobContext;
 use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
 use crate::workspace::{Workspace, paths};
 
+// ── WorkspaceResolver ──────────────────────────────────────────────
+
+/// Resolves a workspace for a given user ID.
+///
+/// In single-user mode, always returns the same workspace.
+/// In multi-tenant mode, creates per-user workspaces on demand.
+#[async_trait]
+pub trait WorkspaceResolver: Send + Sync {
+    async fn resolve(&self, user_id: &str) -> Arc<Workspace>;
+}
+
+/// Returns a fixed workspace regardless of user ID (single-user mode).
+pub struct FixedWorkspaceResolver {
+    workspace: Arc<Workspace>,
+}
+
+impl FixedWorkspaceResolver {
+    pub fn new(workspace: Arc<Workspace>) -> Self {
+        Self { workspace }
+    }
+}
+
+#[async_trait]
+impl WorkspaceResolver for FixedWorkspaceResolver {
+    async fn resolve(&self, _user_id: &str) -> Arc<Workspace> {
+        Arc::clone(&self.workspace)
+    }
+}
+
 /// Detect paths that are clearly local filesystem references, not workspace-memory docs.
 ///
 /// Examples:
@@ -62,13 +91,20 @@ fn map_write_err(e: crate::error::WorkspaceError) -> ToolError {
 /// The agent should call this tool before answering questions about
 /// prior work, decisions, preferences, or any historical context.
 pub struct MemorySearchTool {
-    workspace: Arc<Workspace>,
+    resolver: Arc<dyn WorkspaceResolver>,
 }
 
 impl MemorySearchTool {
-    /// Create a new memory search tool.
-    pub fn new(workspace: Arc<Workspace>) -> Self {
-        Self { workspace }
+    /// Create a new memory search tool with a workspace resolver.
+    pub fn new(resolver: Arc<dyn WorkspaceResolver>) -> Self {
+        Self { resolver }
+    }
+
+    /// Create from a fixed workspace (backward compatibility).
+    pub fn from_workspace(workspace: Arc<Workspace>) -> Self {
+        Self {
+            resolver: Arc::new(FixedWorkspaceResolver::new(workspace)),
+        }
     }
 }
 
@@ -107,7 +143,7 @@ impl Tool for MemorySearchTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -119,8 +155,8 @@ impl Tool for MemorySearchTool {
             .unwrap_or(5)
             .min(20) as usize;
 
-        let results = self
-            .workspace
+        let workspace = self.resolver.resolve(&ctx.user_id).await;
+        let results = workspace
             .search(query, limit)
             .await
             .map_err(|e| ToolError::ExecutionFailed(format!("Search failed: {}", e)))?;
@@ -151,13 +187,20 @@ impl Tool for MemorySearchTool {
 /// Use this to persist important information that should be remembered
 /// across sessions: decisions, preferences, facts, lessons learned.
 pub struct MemoryWriteTool {
-    workspace: Arc<Workspace>,
+    resolver: Arc<dyn WorkspaceResolver>,
 }
 
 impl MemoryWriteTool {
-    /// Create a new memory write tool.
-    pub fn new(workspace: Arc<Workspace>) -> Self {
-        Self { workspace }
+    /// Create a new memory write tool with a workspace resolver.
+    pub fn new(resolver: Arc<dyn WorkspaceResolver>) -> Self {
+        Self { resolver }
+    }
+
+    /// Create from a fixed workspace (backward compatibility).
+    pub fn from_workspace(workspace: Arc<Workspace>) -> Self {
+        Self {
+            resolver: Arc::new(FixedWorkspaceResolver::new(workspace)),
+        }
     }
 }
 
@@ -231,19 +274,21 @@ impl Tool for MemoryWriteTool {
             )));
         }
 
+        let workspace = self.resolver.resolve(&ctx.user_id).await;
+
         // Bootstrap target: clear BOOTSTRAP.md to mark first-run ritual complete.
         // Handled early because it accepts empty content (unlike other targets).
         if target == "bootstrap" {
             // Write empty content to effectively disable the bootstrap injection.
             // system_prompt_for_context() skips empty files.
-            self.workspace
+            workspace
                 .write(paths::BOOTSTRAP, "")
                 .await
                 .map_err(map_write_err)?;
 
             // Also set the in-memory flag so BOOTSTRAP.md injection stops
             // immediately without waiting for a restart.
-            self.workspace.mark_bootstrap_completed();
+            workspace.mark_bootstrap_completed();
 
             let output = serde_json::json!({
                 "status": "cleared",
@@ -289,12 +334,12 @@ impl Tool for MemoryWriteTool {
         // Otherwise, use default workspace methods (which include injection scanning).
         let layer_result = if let Some(layer_name) = layer {
             let result = if append {
-                self.workspace
+                workspace
                     .append_to_layer(layer_name, &resolved_path, content, force)
                     .await
                     .map_err(map_write_err)?
             } else {
-                self.workspace
+                workspace
                     .write_to_layer(layer_name, &resolved_path, content, force)
                     .await
                     .map_err(map_write_err)?
@@ -307,31 +352,33 @@ impl Tool for MemoryWriteTool {
             match target {
                 "memory" => {
                     if append {
-                        self.workspace
+                        workspace
                             .append_memory(content)
                             .await
                             .map_err(map_write_err)?;
                     } else {
-                        self.workspace
+                        workspace
                             .write(paths::MEMORY, content)
                             .await
                             .map_err(map_write_err)?;
                     }
                 }
                 "daily_log" => {
-                    self.workspace
+                    let tz = crate::timezone::parse_timezone(&ctx.user_timezone)
+                        .unwrap_or(chrono_tz::Tz::UTC);
+                    workspace
                         .append_daily_log_tz(content, tz)
                         .await
                         .map_err(map_write_err)?;
                 }
                 _ => {
                     if append {
-                        self.workspace
+                        workspace
                             .append(&resolved_path, content)
                             .await
                             .map_err(map_write_err)?;
                     } else {
-                        self.workspace
+                        workspace
                             .write(&resolved_path, content)
                             .await
                             .map_err(map_write_err)?;
@@ -361,12 +408,12 @@ impl Tool for MemoryWriteTool {
         };
         let mut synced_docs: Vec<&str> = Vec::new();
         if normalized_path == paths::PROFILE {
-            match self.workspace.sync_profile_documents().await {
+            match workspace.sync_profile_documents().await {
                 Ok(true) => {
                     tracing::info!("profile write: synced USER.md + assistant-directives.md");
                     synced_docs.extend_from_slice(&[paths::USER, paths::ASSISTANT_DIRECTIVES]);
 
-                    self.workspace.mark_bootstrap_completed();
+                    workspace.mark_bootstrap_completed();
                     let toml_path = crate::settings::Settings::default_toml_path();
                     if let Ok(Some(mut settings)) = crate::settings::Settings::load_toml(&toml_path)
                         && !settings.profile_onboarding_completed
@@ -416,13 +463,20 @@ impl Tool for MemoryWriteTool {
 ///
 /// Use this to read the full content of any file in the workspace.
 pub struct MemoryReadTool {
-    workspace: Arc<Workspace>,
+    resolver: Arc<dyn WorkspaceResolver>,
 }
 
 impl MemoryReadTool {
-    /// Create a new memory read tool.
-    pub fn new(workspace: Arc<Workspace>) -> Self {
-        Self { workspace }
+    /// Create a new memory read tool with a workspace resolver.
+    pub fn new(resolver: Arc<dyn WorkspaceResolver>) -> Self {
+        Self { resolver }
+    }
+
+    /// Create from a fixed workspace (backward compatibility).
+    pub fn from_workspace(workspace: Arc<Workspace>) -> Self {
+        Self {
+            resolver: Arc::new(FixedWorkspaceResolver::new(workspace)),
+        }
     }
 }
 
@@ -456,7 +510,7 @@ impl Tool for MemoryReadTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -470,8 +524,8 @@ impl Tool for MemoryReadTool {
             )));
         }
 
-        let doc = self
-            .workspace
+        let workspace = self.resolver.resolve(&ctx.user_id).await;
+        let doc = workspace
             .read(path)
             .await
             .map_err(|e| ToolError::ExecutionFailed(format!("Read failed: {}", e)))?;
@@ -495,20 +549,27 @@ impl Tool for MemoryReadTool {
 ///
 /// Returns a hierarchical view of files and directories with configurable depth.
 pub struct MemoryTreeTool {
-    workspace: Arc<Workspace>,
+    resolver: Arc<dyn WorkspaceResolver>,
 }
 
 impl MemoryTreeTool {
-    /// Create a new memory tree tool.
-    pub fn new(workspace: Arc<Workspace>) -> Self {
-        Self { workspace }
+    /// Create a new memory tree tool with a workspace resolver.
+    pub fn new(resolver: Arc<dyn WorkspaceResolver>) -> Self {
+        Self { resolver }
+    }
+
+    /// Create from a fixed workspace (backward compatibility).
+    pub fn from_workspace(workspace: Arc<Workspace>) -> Self {
+        Self {
+            resolver: Arc::new(FixedWorkspaceResolver::new(workspace)),
+        }
     }
 
     /// Recursively build tree structure.
     ///
     /// Returns a compact format where directories end with `/` and may have children.
     async fn build_tree(
-        &self,
+        workspace: &Arc<Workspace>,
         path: &str,
         current_depth: usize,
         max_depth: usize,
@@ -517,8 +578,7 @@ impl MemoryTreeTool {
             return Ok(Vec::new());
         }
 
-        let entries = self
-            .workspace
+        let entries = workspace
             .list(path)
             .await
             .map_err(|e| ToolError::ExecutionFailed(format!("Tree failed: {}", e)))?;
@@ -533,8 +593,13 @@ impl MemoryTreeTool {
             };
 
             if entry.is_directory && current_depth < max_depth {
-                let children =
-                    Box::pin(self.build_tree(&entry.path, current_depth + 1, max_depth)).await?;
+                let children = Box::pin(Self::build_tree(
+                    workspace,
+                    &entry.path,
+                    current_depth + 1,
+                    max_depth,
+                ))
+                .await?;
                 if children.is_empty() {
                     result.push(serde_json::Value::String(display_path));
                 } else {
@@ -584,7 +649,7 @@ impl Tool for MemoryTreeTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -596,7 +661,8 @@ impl Tool for MemoryTreeTool {
             .unwrap_or(1)
             .clamp(1, 10) as usize;
 
-        let tree = self.build_tree(path, 1, depth).await?;
+        let workspace = self.resolver.resolve(&ctx.user_id).await;
+        let tree = Self::build_tree(&workspace, path, 1, depth).await?;
 
         // Compact output: just the tree array
         Ok(ToolOutput::success(
@@ -650,7 +716,7 @@ mod tests {
         #[test]
         fn test_memory_search_schema() {
             let workspace = make_test_workspace();
-            let tool = MemorySearchTool::new(workspace);
+            let tool = MemorySearchTool::from_workspace(workspace);
 
             assert_eq!(tool.name(), "memory_search");
             assert!(!tool.requires_sanitization());
@@ -668,7 +734,7 @@ mod tests {
         #[test]
         fn test_memory_write_schema() {
             let workspace = make_test_workspace();
-            let tool = MemoryWriteTool::new(workspace);
+            let tool = MemoryWriteTool::from_workspace(workspace);
 
             assert_eq!(tool.name(), "memory_write");
 
@@ -681,7 +747,7 @@ mod tests {
         #[test]
         fn test_memory_read_schema() {
             let workspace = make_test_workspace();
-            let tool = MemoryReadTool::new(workspace);
+            let tool = MemoryReadTool::from_workspace(workspace);
 
             assert_eq!(tool.name(), "memory_read");
 
@@ -698,7 +764,7 @@ mod tests {
         #[test]
         fn test_memory_tree_schema() {
             let workspace = make_test_workspace();
-            let tool = MemoryTreeTool::new(workspace);
+            let tool = MemoryTreeTool::from_workspace(workspace);
 
             assert_eq!(tool.name(), "memory_tree");
 
@@ -711,7 +777,7 @@ mod tests {
         #[tokio::test]
         async fn test_memory_write_rejects_injection_to_identity_file() {
             let workspace = make_test_workspace();
-            let tool = MemoryWriteTool::new(workspace);
+            let tool = MemoryWriteTool::from_workspace(workspace);
             let ctx = JobContext::default();
 
             let params = serde_json::json!({
@@ -733,4 +799,176 @@ mod tests {
             }
         }
     }
+
+    // Regression tests for per-user workspace scoping (multi-tenant mode).
+    // See: https://github.com/nearai/ironclaw/pull/1118
+    // Bug: memory tools used a single startup workspace regardless of which
+    // user was chatting. Fix: resolve workspace per-request via JobContext.user_id.
+
+    #[cfg(feature = "postgres")]
+    mod resolver_tests {
+        use super::*;
+
+        fn make_test_workspace_for_user(user_id: &str) -> Arc<Workspace> {
+            Arc::new(Workspace::new(
+                user_id,
+                deadpool_postgres::Pool::builder(deadpool_postgres::Manager::new(
+                    tokio_postgres::Config::new(),
+                    tokio_postgres::NoTls,
+                ))
+                .build()
+                .unwrap(),
+            ))
+        }
+
+        #[tokio::test]
+        async fn test_fixed_workspace_resolver_ignores_user_id() {
+            let ws = make_test_workspace_for_user("alice");
+            let resolver = FixedWorkspaceResolver::new(Arc::clone(&ws));
+
+            let ws_alice = resolver.resolve("alice").await;
+            let ws_bob = resolver.resolve("bob").await;
+
+            // Both should return the exact same Arc (pointer equality)
+            assert!(Arc::ptr_eq(&ws_alice, &ws_bob));
+            assert_eq!(ws_alice.user_id(), "alice");
+        }
+
+        /// Tracking resolver that records which user_ids were requested.
+        struct TrackingWorkspaceResolver {
+            inner: FixedWorkspaceResolver,
+            resolved_users: std::sync::Mutex<Vec<String>>,
+        }
+
+        impl TrackingWorkspaceResolver {
+            fn new(workspace: Arc<Workspace>) -> Self {
+                Self {
+                    inner: FixedWorkspaceResolver::new(workspace),
+                    resolved_users: std::sync::Mutex::new(Vec::new()),
+                }
+            }
+
+            fn resolved_users(&self) -> Vec<String> {
+                self.resolved_users.lock().unwrap().clone()
+            }
+        }
+
+        #[async_trait]
+        impl WorkspaceResolver for TrackingWorkspaceResolver {
+            async fn resolve(&self, user_id: &str) -> Arc<Workspace> {
+                self.resolved_users
+                    .lock()
+                    .unwrap()
+                    .push(user_id.to_string());
+                self.inner.resolve(user_id).await
+            }
+        }
+
+        #[tokio::test]
+        async fn test_memory_search_uses_job_context_user_id() {
+            let ws = make_test_workspace_for_user("default");
+            let tracker = Arc::new(TrackingWorkspaceResolver::new(ws));
+            let tool = MemorySearchTool::new(tracker.clone() as Arc<dyn WorkspaceResolver>);
+
+            // Execute with user_id "alice"
+            let ctx_alice = JobContext::with_user("alice", "test", "test");
+            let params = serde_json::json!({"query": "test"});
+            // The search will fail (no real DB) but we only care about resolver call
+            let _ = tool.execute(params, &ctx_alice).await;
+
+            // Execute with user_id "bob"
+            let ctx_bob = JobContext::with_user("bob", "test", "test");
+            let params = serde_json::json!({"query": "test"});
+            let _ = tool.execute(params, &ctx_bob).await;
+
+            let resolved = tracker.resolved_users();
+            assert_eq!(resolved, vec!["alice", "bob"]);
+        }
+
+        #[tokio::test]
+        async fn test_memory_write_uses_job_context_user_id() {
+            let ws = make_test_workspace_for_user("default");
+            let tracker = Arc::new(TrackingWorkspaceResolver::new(ws));
+            let tool = MemoryWriteTool::new(tracker.clone() as Arc<dyn WorkspaceResolver>);
+
+            // Execute with user_id "alice"
+            let ctx_alice = JobContext::with_user("alice", "test", "test");
+            let params = serde_json::json!({
+                "content": "remember this",
+                "target": "daily_log",
+            });
+            let _ = tool.execute(params, &ctx_alice).await;
+
+            // Execute with user_id "bob"
+            let ctx_bob = JobContext::with_user("bob", "test", "test");
+            let params = serde_json::json!({
+                "content": "remember that",
+                "target": "daily_log",
+            });
+            let _ = tool.execute(params, &ctx_bob).await;
+
+            let resolved = tracker.resolved_users();
+            assert_eq!(resolved, vec!["alice", "bob"]);
+        }
+    }
+
+    #[cfg(feature = "libsql")]
+    mod per_user_resolver_tests {
+        use super::*;
+
+        async fn make_test_db() -> Arc<dyn crate::db::Database> {
+            use crate::db::libsql::LibSqlBackend;
+            let temp_dir = tempfile::tempdir().expect("tempdir");
+            let db_path = temp_dir.path().join("resolver_test.db");
+            let backend = LibSqlBackend::new_local(&db_path)
+                .await
+                .expect("LibSqlBackend");
+            <LibSqlBackend as crate::db::Database>::run_migrations(&backend)
+                .await
+                .expect("migrations");
+            // Leak the tempdir so it outlives the test (cleaned up on process exit).
+            std::mem::forget(temp_dir);
+            Arc::new(backend)
+        }
+
+        #[tokio::test]
+        async fn test_workspace_pool_resolver_returns_different_workspaces() {
+            let db = make_test_db().await;
+
+            let pool = crate::channels::web::server::WorkspacePool::new(
+                db,
+                None,
+                crate::workspace::EmbeddingCacheConfig::default(),
+                crate::config::WorkspaceSearchConfig::default(),
+                crate::config::WorkspaceConfig::default(),
+            );
+
+            let ws_alice = pool.resolve("alice").await;
+            let ws_bob = pool.resolve("bob").await;
+
+            // Different user IDs should get different workspaces
+            assert_eq!(ws_alice.user_id(), "alice");
+            assert_eq!(ws_bob.user_id(), "bob");
+            assert!(!Arc::ptr_eq(&ws_alice, &ws_bob));
+        }
+
+        #[tokio::test]
+        async fn test_workspace_pool_resolver_caches_workspace() {
+            let db = make_test_db().await;
+
+            let pool = crate::channels::web::server::WorkspacePool::new(
+                db,
+                None,
+                crate::workspace::EmbeddingCacheConfig::default(),
+                crate::config::WorkspaceSearchConfig::default(),
+                crate::config::WorkspaceConfig::default(),
+            );
+
+            let ws1 = pool.resolve("alice").await;
+            let ws2 = pool.resolve("alice").await;
+
+            // Same user_id should return the same cached Arc (pointer equality)
+            assert!(Arc::ptr_eq(&ws1, &ws2));
+        }
+    }
 }

src/tools/builtin/mod.rs

@@ -6,7 +6,7 @@ mod file;
 mod http;
 mod job;
 mod json;
-mod memory;
+pub mod memory;
 mod message;
 pub mod path_utils;
 mod restart;

src/tools/builtin/routine.rs

@@ -608,7 +608,8 @@ fn routine_create_schema(include_compatibility_aliases: bool) -> Value {
 }
 
 pub(crate) fn routine_create_parameters_schema() -> Value {
-    routine_create_schema(false)
+    static CACHE: OnceLock<Value> = OnceLock::new();
+    CACHE.get_or_init(|| routine_create_schema(false)).clone()
 }
 
 fn routine_create_discovery_schema() -> Value {
@@ -1014,7 +1015,8 @@ fn event_emit_schema(include_source_alias: bool) -> Value {
 }
 
 pub(crate) fn event_emit_parameters_schema() -> Value {
-    event_emit_schema(false)
+    static CACHE: OnceLock<Value> = OnceLock::new();
+    CACHE.get_or_init(|| event_emit_schema(false)).clone()
 }
 
 fn event_emit_discovery_schema() -> Value {

src/tools/registry.rs

@@ -334,15 +334,37 @@ impl ToolRegistry {
         tracing::debug!("Registered 5 development tools");
     }
 
-    /// Register memory tools with a workspace.
+    /// Register memory tools with a workspace resolver.
+    ///
+    /// Memory tools require a workspace resolver for persistence. Call this after
+    /// `register_builtin_tools()` if you have a workspace available.
+    pub fn register_memory_tools_with_resolver(
+        &self,
+        resolver: Arc<dyn crate::tools::builtin::memory::WorkspaceResolver>,
+    ) {
+        self.register_sync(Arc::new(MemorySearchTool::new(Arc::clone(&resolver))));
+        self.register_sync(Arc::new(MemoryWriteTool::new(Arc::clone(&resolver))));
+        self.register_sync(Arc::new(MemoryReadTool::new(Arc::clone(&resolver))));
+        self.register_sync(Arc::new(MemoryTreeTool::new(resolver)));
+
+        tracing::debug!("Registered 4 memory tools");
+    }
+
+    /// Register memory tools with a fixed workspace (backward compatibility).
     ///
     /// Memory tools require a workspace for persistence. Call this after
     /// `register_builtin_tools()` if you have a workspace available.
     pub fn register_memory_tools(&self, workspace: Arc<Workspace>) {
-        self.register_sync(Arc::new(MemorySearchTool::new(Arc::clone(&workspace))));
-        self.register_sync(Arc::new(MemoryWriteTool::new(Arc::clone(&workspace))));
-        self.register_sync(Arc::new(MemoryReadTool::new(Arc::clone(&workspace))));
-        self.register_sync(Arc::new(MemoryTreeTool::new(workspace)));
+        self.register_sync(Arc::new(MemorySearchTool::from_workspace(Arc::clone(
+            &workspace,
+        ))));
+        self.register_sync(Arc::new(MemoryWriteTool::from_workspace(Arc::clone(
+            &workspace,
+        ))));
+        self.register_sync(Arc::new(MemoryReadTool::from_workspace(Arc::clone(
+            &workspace,
+        ))));
+        self.register_sync(Arc::new(MemoryTreeTool::from_workspace(workspace)));
 
         tracing::debug!("Registered 4 memory tools");
     }
@@ -361,7 +383,11 @@ impl ToolRegistry {
         job_manager: Option<Arc<ContainerJobManager>>,
         store: Option<Arc<dyn Database>>,
         job_event_tx: Option<
-            tokio::sync::broadcast::Sender<(uuid::Uuid, crate::channels::web::types::SseEvent)>,
+            tokio::sync::broadcast::Sender<(
+                uuid::Uuid,
+                String,
+                crate::channels::web::types::SseEvent,
+            )>,
         >,
         inject_tx: Option<tokio::sync::mpsc::Sender<crate::channels::IncomingMessage>>,
         prompt_queue: Option<PromptQueue>,

src/tools/wasm/capabilities_schema.rs

@@ -47,12 +47,6 @@ pub struct CapabilitiesFile {
     #[serde(default)]
     pub description: Option<String>,
 
-    /// JSON Schema for the tool's input parameters.
-    /// Used as the `Tool::parameters_schema()` return value.
-    /// If omitted, a permissive fallback is used (with a warning).
-    #[serde(default)]
-    pub parameters: Option<serde_json::Value>,
-
     /// Extension version (semver).
     #[serde(default)]
     pub version: Option<String>,
@@ -103,9 +97,6 @@ pub struct CapabilitiesFile {
 
 /// Maximum length for the description field to prevent memory abuse.
 const MAX_DESCRIPTION_CHARS: usize = 4096;
-/// Maximum serialized size of the parameters schema JSON.
-const MAX_PARAMETERS_SCHEMA_BYTES: usize = 64 * 1024;
-
 impl CapabilitiesFile {
     /// Parse from JSON string.
     pub fn from_json(json: &str) -> Result<Self, serde_json::Error> {
@@ -135,18 +126,6 @@ impl CapabilitiesFile {
             );
             self.description = Some(truncated.to_string());
         }
-        // Drop oversized parameters schema (issue #977)
-        if let Some(ref params) = self.parameters {
-            let size = params.to_string().len();
-            if size > MAX_PARAMETERS_SCHEMA_BYTES {
-                tracing::warn!(
-                    "Capabilities parameters schema dropped ({} bytes exceeds {} limit)",
-                    size,
-                    MAX_PARAMETERS_SCHEMA_BYTES,
-                );
-                self.parameters = None;
-            }
-        }
     }
 
     /// Merge nested `capabilities` wrapper into top-level fields.
@@ -171,7 +150,6 @@ impl CapabilitiesFile {
         if let Some(inner) = self.capabilities.take() {
             let inner = inner.resolve_nested_inner(depth + 1);
             self.description = self.description.or(inner.description);
-            self.parameters = self.parameters.or(inner.parameters);
             self.http = self.http.or(inner.http);
             self.secrets = self.secrets.or(inner.secrets);
             self.tool_invoke = self.tool_invoke.or(inner.tool_invoke);
@@ -1424,26 +1402,12 @@ mod tests {
         );
     }
 
-    // ── Tool description and parameters schema ──────────────────────────
+    // ── Tool description ────────────────────────────────────────────────
 
     #[test]
-    fn test_parse_description_and_parameters() {
+    fn test_parse_description() {
         let json = r#"{
-            "description": "Search the web using Brave Search API",
-            "parameters": {
-                "type": "object",
-                "properties": {
-                    "query": {
-                        "type": "string",
-                        "description": "Search query"
-                    },
-                    "count": {
-                        "type": "integer",
-                        "description": "Number of results"
-                    }
-                },
-                "required": ["query"]
-            }
+            "description": "Search the web using Brave Search API"
         }"#;
 
         let caps = CapabilitiesFile::from_json(json).unwrap();
@@ -1451,28 +1415,10 @@ mod tests {
             caps.description.as_deref(),
             Some("Search the web using Brave Search API")
         );
-        let params = caps.parameters.unwrap();
-        assert_eq!(params["type"], "object");
-        assert!(params["properties"]["query"].is_object());
-        assert_eq!(params["required"][0], "query");
     }
 
     #[test]
-    fn test_parse_description_only() {
-        let json = r#"{
-            "description": "A tool without explicit parameters schema"
-        }"#;
-
-        let caps = CapabilitiesFile::from_json(json).unwrap();
-        assert_eq!(
-            caps.description.as_deref(),
-            Some("A tool without explicit parameters schema")
-        );
-        assert!(caps.parameters.is_none());
-    }
-
-    #[test]
-    fn test_parse_without_description_or_parameters() {
+    fn test_parse_without_description() {
         let json = r#"{
             "http": {
                 "allowlist": [{ "host": "api.example.com" }]
@@ -1484,24 +1430,28 @@ mod tests {
             caps.description.is_none(),
             "description should be None when not provided"
         );
-        assert!(
-            caps.parameters.is_none(),
-            "parameters should be None when not provided"
-        );
+    }
+
+    #[test]
+    fn test_parameters_field_silently_ignored() {
+        // Backward compat: old capabilities files with "parameters" still parse.
+        let json = r#"{
+            "description": "A tool",
+            "parameters": {
+                "type": "object",
+                "properties": { "action": { "type": "string" } }
+            }
+        }"#;
+
+        let caps = CapabilitiesFile::from_json(json).unwrap();
+        assert_eq!(caps.description.as_deref(), Some("A tool"));
     }
 
     #[test]
     fn test_resolve_nested_description_promoted() {
         let json = r#"{
             "capabilities": {
-                "description": "Inner tool description",
-                "parameters": {
-                    "type": "object",
-                    "properties": {
-                        "input": { "type": "string" }
-                    },
-                    "required": ["input"]
-                }
+                "description": "Inner tool description"
             }
         }"#;
 
@@ -1511,10 +1461,6 @@ mod tests {
             Some("Inner tool description"),
             "description should be promoted from inner capabilities"
         );
-        assert!(
-            caps.parameters.is_some(),
-            "parameters should be promoted from inner capabilities"
-        );
     }
 
     #[test]
@@ -1564,32 +1510,4 @@ mod tests {
             desc.len()
         );
     }
-
-    /// Regression test for issue #977: oversized parameters schema is dropped.
-    #[test]
-    fn test_oversized_parameters_schema_dropped() {
-        // Build a parameters schema larger than MAX_PARAMETERS_SCHEMA_BYTES
-        let mut properties = serde_json::Map::new();
-        for i in 0..2000 {
-            properties.insert(
-                format!("field_{i}"),
-                serde_json::json!({
-                    "type": "string",
-                    "description": "x".repeat(50)
-                }),
-            );
-        }
-        let schema = serde_json::json!({
-            "type": "object",
-            "properties": properties,
-        });
-        let json = serde_json::json!({
-            "parameters": schema,
-        });
-        let caps = CapabilitiesFile::from_json(&json.to_string()).unwrap();
-        assert!(
-            caps.parameters.is_none(),
-            "oversized parameters schema should be dropped"
-        );
-    }
 }

src/tools/wasm/loader.rs

@@ -123,73 +123,51 @@ impl WasmToolLoader {
         }
         let wasm_bytes = fs::read(wasm_path).await?;
 
-        // Read capabilities (optional) and extract OAuth refresh config,
-        // tool description, and parameter schema.
-        let (capabilities, oauth_refresh, description, schema) =
-            if let Some(cap_path) = capabilities_path {
-                if cap_path.exists() {
-                    let cap_bytes = fs::read(cap_path).await?;
-                    let cap_file = CapabilitiesFile::from_bytes(&cap_bytes)
-                        .map_err(|e| WasmLoadError::InvalidCapabilities(e.to_string()))?;
-                    cap_file.validate(name);
+        // Read capabilities (optional) and extract OAuth refresh config
+        // and tool description. Parameter schema is auto-derived from the
+        // WASM module's schema() export (see WasmToolSchemas::compact_schema).
+        let (capabilities, oauth_refresh, description) = if let Some(cap_path) = capabilities_path {
+            if cap_path.exists() {
+                let cap_bytes = fs::read(cap_path).await?;
+                let cap_file = CapabilitiesFile::from_bytes(&cap_bytes)
+                    .map_err(|e| WasmLoadError::InvalidCapabilities(e.to_string()))?;
+                cap_file.validate(name);
 
-                    // Check WIT version compatibility
-                    check_wit_version_compat(
-                        name,
-                        cap_file.wit_version.as_deref(),
-                        crate::tools::wasm::WIT_TOOL_VERSION,
-                    )?;
+                // Check WIT version compatibility
+                check_wit_version_compat(
+                    name,
+                    cap_file.wit_version.as_deref(),
+                    crate::tools::wasm::WIT_TOOL_VERSION,
+                )?;
 
-                    let caps = cap_file.to_capabilities();
-                    let oauth = resolve_oauth_refresh_config(&cap_file);
-                    let desc = cap_file.description.clone();
-                    // Validate parameters schema before accepting it.
-                    let params = cap_file.parameters.clone().and_then(|p| {
-                        let errors = crate::tools::validate_tool_schema(&p, name);
-                        if errors.is_empty() {
-                            Some(p)
-                        } else {
-                            tracing::warn!(
-                                tool = name,
-                                ?errors,
-                                "Invalid parameters schema in capabilities.json, \
-                                 using permissive fallback"
-                            );
-                            None
-                        }
-                    });
-                    if desc.is_none() {
-                        tracing::warn!(
-                            tool = name,
-                            path = %cap_path.display(),
-                            "Capabilities file missing \"description\" field; \
-                             tool will use generic fallback description"
-                        );
-                    }
-                    if params.is_none() && cap_file.parameters.is_none() {
-                        tracing::warn!(
-                            tool = name,
-                            path = %cap_path.display(),
-                            "Capabilities file missing \"parameters\" field; \
-                             tool will accept any JSON object (permissive fallback)"
-                        );
-                    }
-                    (caps, oauth, desc, params)
-                } else {
+                let caps = cap_file.to_capabilities();
+                let oauth = resolve_oauth_refresh_config(&cap_file);
+                let desc = cap_file.description.clone();
+                if desc.is_none() {
                     tracing::warn!(
+                        tool = name,
                         path = %cap_path.display(),
-                        "Capabilities file not found, using default (no permissions)"
+                        "Capabilities file missing \"description\" field; \
+                         tool will use generic fallback description"
                     );
-                    (Capabilities::default(), None, None, None)
                 }
+                (caps, oauth, desc)
             } else {
                 tracing::warn!(
                     tool = name,
-                    "No capabilities file for WASM tool; \
-                     tool will use generic fallback description and accept any JSON object"
+                    path = %cap_path.display(),
+                    "Capabilities file not found, using default (no permissions)"
                 );
-                (Capabilities::default(), None, None, None)
-            };
+                (Capabilities::default(), None, None)
+            }
+        } else {
+            tracing::warn!(
+                tool = name,
+                "No capabilities file for WASM tool; \
+                     tool will use generic fallback description"
+            );
+            (Capabilities::default(), None, None)
+        };
 
         // Register the tool
         self.registry
@@ -200,7 +178,7 @@ impl WasmToolLoader {
                 capabilities,
                 limits: None,
                 description: description.as_deref(),
-                schema,
+                schema: None,
                 secrets_store: self.secrets_store.clone(),
                 oauth_refresh,
             })
@@ -440,6 +418,7 @@ fn resolve_oauth_refresh_config(cap_file: &CapabilitiesFile) -> Option<OAuthRefr
     let oauth = auth.oauth.as_ref()?;
 
     let builtin = crate::cli::oauth_defaults::builtin_credentials(&auth.secret_name);
+    let exchange_proxy_url = crate::cli::oauth_defaults::exchange_proxy_url();
 
     let client_id = oauth
         .client_id
@@ -462,11 +441,21 @@ fn resolve_oauth_refresh_config(cap_file: &CapabilitiesFile) -> Option<OAuthRefr
                 .and_then(|env| std::env::var(env).ok())
         })
         .or_else(|| builtin.as_ref().map(|c| c.client_secret.to_string()));
+    let client_secret = crate::cli::oauth_defaults::hosted_proxy_client_secret(
+        &client_secret,
+        builtin.as_ref(),
+        exchange_proxy_url.is_some(),
+    );
+    let gateway_token = crate::config::helpers::env_or_override("GATEWAY_AUTH_TOKEN")
+        .map(|token| token.trim().to_string())
+        .filter(|token| !token.is_empty());
 
     Some(OAuthRefreshConfig {
         token_url: oauth.token_url.clone(),
         client_id,
         client_secret,
+        exchange_proxy_url,
+        gateway_token,
         secret_name: auth.secret_name.clone(),
         provider: auth.provider.clone(),
     })
@@ -733,9 +722,44 @@ mod tests {
 
     use tempfile::TempDir;
 
+    use crate::config::helpers::lock_env;
     use crate::testing::credentials::{TEST_OAUTH_CLIENT_ID, TEST_OAUTH_CLIENT_SECRET};
     use crate::tools::wasm::loader::{WasmLoadError, check_wit_version_compat, discover_tools};
 
+    /// Restores a test-scoped env var override on drop.
+    struct EnvVarGuard {
+        key: String,
+        previous: Option<String>,
+    }
+
+    impl Drop for EnvVarGuard {
+        fn drop(&mut self) {
+            // SAFETY: Tests use lock_env() to serialize environment access.
+            unsafe {
+                if let Some(ref value) = self.previous {
+                    std::env::set_var(&self.key, value);
+                } else {
+                    std::env::remove_var(&self.key);
+                }
+            }
+        }
+    }
+
+    fn set_env_var(key: &str, value: Option<&str>) -> EnvVarGuard {
+        let previous = std::env::var(key).ok();
+        // SAFETY: Tests use lock_env() to serialize environment access.
+        unsafe {
+            match value {
+                Some(value) => std::env::set_var(key, value),
+                None => std::env::remove_var(key),
+            }
+        }
+        EnvVarGuard {
+            key: key.to_string(),
+            previous,
+        }
+    }
+
     #[test]
     fn wit_version_compat_none_is_ok() {
         // Pre-versioning extensions (no wit_version declared) should always pass
@@ -893,6 +917,8 @@ mod tests {
             config.client_secret,
             Some(TEST_OAUTH_CLIENT_SECRET.to_string())
         );
+        assert_eq!(config.exchange_proxy_url, None);
+        assert_eq!(config.gateway_token, None);
         assert_eq!(config.secret_name, "google_oauth_token");
         assert_eq!(config.provider, Some("google".to_string()));
     }
@@ -953,6 +979,10 @@ mod tests {
             AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
         };
 
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", None);
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+
         // google_oauth_token should fall back to built-in credentials
         let caps = CapabilitiesFile {
             auth: Some(AuthCapabilitySchema {
@@ -974,6 +1004,95 @@ mod tests {
         let config = config.unwrap();
         assert!(!config.client_id.is_empty());
         assert!(config.client_secret.is_some());
+        assert_eq!(config.exchange_proxy_url, None);
+        assert_eq!(config.gateway_token, None);
+    }
+
+    #[test]
+    fn test_resolve_oauth_refresh_config_hosted_proxy_populates_env_and_suppresses_builtin_secret()
+    {
+        use crate::tools::wasm::capabilities_schema::{
+            AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
+        };
+
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var(
+            "IRONCLAW_OAUTH_EXCHANGE_URL",
+            Some("https://compose-api.example.com"),
+        );
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+        let _client_id_guard =
+            set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
+
+        let caps = CapabilitiesFile {
+            auth: Some(AuthCapabilitySchema {
+                secret_name: "google_oauth_token".to_string(),
+                provider: Some("google".to_string()),
+                oauth: Some(OAuthConfigSchema {
+                    authorization_url: "https://accounts.google.com/o/oauth2/v2/auth".to_string(),
+                    token_url: "https://oauth2.googleapis.com/token".to_string(),
+                    client_id_env: Some("GOOGLE_OAUTH_CLIENT_ID".to_string()),
+                    ..Default::default()
+                }),
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let config = super::resolve_oauth_refresh_config(&caps).expect("hosted oauth config");
+        assert_eq!(config.client_id, "hosted-google-client-id");
+        assert_eq!(config.client_secret, None);
+        assert_eq!(
+            config.exchange_proxy_url.as_deref(),
+            Some("https://compose-api.example.com")
+        );
+        assert_eq!(config.gateway_token.as_deref(), Some("gateway-test-token"));
+    }
+
+    #[test]
+    fn test_resolve_oauth_refresh_config_hosted_proxy_preserves_explicit_secret() {
+        use crate::tools::wasm::capabilities_schema::{
+            AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
+        };
+
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var(
+            "IRONCLAW_OAUTH_EXCHANGE_URL",
+            Some("https://compose-api.example.com"),
+        );
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+        let _client_id_guard =
+            set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
+        let _client_secret_guard =
+            set_env_var("GOOGLE_OAUTH_CLIENT_SECRET", Some("hosted-server-secret"));
+
+        let caps = CapabilitiesFile {
+            auth: Some(AuthCapabilitySchema {
+                secret_name: "google_oauth_token".to_string(),
+                provider: Some("google".to_string()),
+                oauth: Some(OAuthConfigSchema {
+                    authorization_url: "https://accounts.google.com/o/oauth2/v2/auth".to_string(),
+                    token_url: "https://oauth2.googleapis.com/token".to_string(),
+                    client_id_env: Some("GOOGLE_OAUTH_CLIENT_ID".to_string()),
+                    client_secret_env: Some("GOOGLE_OAUTH_CLIENT_SECRET".to_string()),
+                    ..Default::default()
+                }),
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let config = super::resolve_oauth_refresh_config(&caps).expect("hosted oauth config");
+        assert_eq!(config.client_id, "hosted-google-client-id");
+        assert_eq!(
+            config.client_secret.as_deref(),
+            Some("hosted-server-secret")
+        );
+        assert_eq!(
+            config.exchange_proxy_url.as_deref(),
+            Some("https://compose-api.example.com")
+        );
+        assert_eq!(config.gateway_token.as_deref(), Some("gateway-test-token"));
     }
 
     // ---------------------------------------------------------------

src/tools/wasm/wrapper.rs

@@ -19,7 +19,7 @@ use wasmtime_wasi::{ResourceTable, WasiCtx, WasiCtxBuilder, WasiView};
 use crate::context::JobContext;
 use crate::llm::recording::{HttpExchangeRequest, HttpExchangeResponse, HttpInterceptor};
 use crate::safety::LeakDetector;
-use crate::secrets::SecretsStore;
+use crate::secrets::{DecryptedSecret, SecretsStore};
 use crate::tools::tool::{Tool, ToolError, ToolOutput};
 use crate::tools::wasm::capabilities::Capabilities;
 use crate::tools::wasm::credential_injector::{
@@ -44,6 +44,7 @@ wasmtime::component::bindgen!({
 });
 
 // Alias the export interface types for convenience.
+use crate::cli::oauth_defaults;
 use exports::near::agent::tool as wit_tool;
 
 /// Configuration needed to refresh an expired OAuth access token.
@@ -59,6 +60,10 @@ pub struct OAuthRefreshConfig {
     pub client_id: String,
     /// OAuth client_secret (optional, some providers use PKCE without a secret).
     pub client_secret: Option<String>,
+    /// Hosted OAuth proxy base URL (e.g., "http://host.docker.internal:8080").
+    pub exchange_proxy_url: Option<String>,
+    /// Gateway auth token for authenticating with the hosted OAuth proxy.
+    pub gateway_token: Option<String>,
     /// Secret name of the access token (e.g., "google_oauth_token").
     /// The refresh token lives at `{secret_name}_refresh_token`.
     pub secret_name: String,
@@ -656,12 +661,125 @@ impl WasmToolSchemas {
     }
 
     fn new(discovery: serde_json::Value) -> Self {
+        let advertised = Self::compact_schema(&discovery);
         Self {
-            advertised: Self::permissive_schema(),
+            advertised,
             discovery,
         }
     }
 
+    /// Derive a compact advertised schema from the full discovery schema.
+    ///
+    /// Collects properties from top-level `properties` and from
+    /// `oneOf`/`anyOf`/`allOf` variants. Keeps only properties that are in
+    /// the top-level `required` array or carry an `enum`/`const` constraint.
+    /// For properties defined via `const` across multiple variants (e.g.
+    /// `"action": {"const": "get_repo"}` in each `oneOf` branch), the `const`
+    /// values are merged into a single `enum` array.
+    ///
+    /// Variant-level `required` fields (e.g. `owner`, `repo` required within
+    /// each `oneOf` variant but not top-level) are intentionally omitted from
+    /// the compact schema — the LLM can discover them via
+    /// `tool_info(detail: "schema")`.
+    ///
+    /// At most `MAX_COMPACT_PROPERTIES` properties are collected to bound
+    /// allocations from adversarial schemas.
+    fn compact_schema(discovery: &serde_json::Value) -> serde_json::Value {
+        const MAX_COMPACT_PROPERTIES: usize = 100;
+
+        let required: std::collections::HashSet<String> = discovery
+            .get("required")
+            .and_then(|r| r.as_array())
+            .map(|arr| {
+                arr.iter()
+                    .filter_map(|v| v.as_str().map(String::from))
+                    .collect()
+            })
+            .unwrap_or_default();
+
+        // Collect properties from top-level and oneOf/anyOf/allOf variants.
+        // For properties with `const` across variants, merge into an `enum`.
+        let mut all_properties = serde_json::Map::new();
+        // Track const values per property to merge into enum.
+        let mut const_values: std::collections::HashMap<String, Vec<serde_json::Value>> =
+            std::collections::HashMap::new();
+
+        if let Some(props) = discovery.get("properties").and_then(|p| p.as_object()) {
+            for (k, v) in props {
+                if all_properties.len() >= MAX_COMPACT_PROPERTIES {
+                    break;
+                }
+                all_properties.insert(k.clone(), v.clone());
+            }
+        }
+        for key in ["oneOf", "anyOf", "allOf"] {
+            if let Some(variants) = discovery.get(key).and_then(|v| v.as_array()) {
+                for variant in variants {
+                    if let Some(props) = variant.get("properties").and_then(|p| p.as_object()) {
+                        for (k, v) in props {
+                            if all_properties.len() >= MAX_COMPACT_PROPERTIES
+                                && !all_properties.contains_key(k)
+                            {
+                                continue;
+                            }
+                            // Track const values for merging into enum.
+                            if let Some(c) = v.get("const") {
+                                const_values.entry(k.clone()).or_default().push(c.clone());
+                            }
+                            all_properties.entry(k.clone()).or_insert_with(|| v.clone());
+                        }
+                    }
+                }
+            }
+        }
+
+        // Merge collected const values into enum arrays.
+        for (name, values) in &const_values {
+            if values.len() > 1
+                && let Some(prop) = all_properties.get_mut(name)
+            {
+                let mut merged = prop.clone();
+                if let Some(obj) = merged.as_object_mut() {
+                    obj.remove("const");
+                    obj.insert("enum".to_string(), serde_json::Value::Array(values.clone()));
+                }
+                *prop = merged;
+            }
+        }
+
+        if all_properties.is_empty() {
+            return Self::permissive_schema();
+        }
+
+        let kept: serde_json::Map<String, serde_json::Value> = all_properties
+            .into_iter()
+            .filter(|(name, prop)| {
+                required.contains(name) || prop.get("enum").is_some() || prop.get("const").is_some()
+            })
+            .collect();
+
+        if kept.is_empty() {
+            return Self::permissive_schema();
+        }
+
+        let kept_required: Vec<serde_json::Value> = required
+            .iter()
+            .filter(|name| kept.contains_key(name.as_str()))
+            .map(|name| serde_json::Value::String(name.clone()))
+            .collect();
+
+        let mut result = serde_json::json!({
+            "type": "object",
+            "properties": kept,
+            "additionalProperties": true,
+        });
+        if !kept_required.is_empty() {
+            result["required"] = serde_json::Value::Array(kept_required);
+        }
+
+        result
+    }
+
     fn with_override(&self, schema: serde_json::Value) -> Self {
         Self {
             advertised: schema.clone(),
@@ -1097,6 +1215,53 @@ async fn refresh_oauth_token(
     user_id: &str,
     config: &OAuthRefreshConfig,
 ) -> bool {
+    let refresh_name = format!("{}_refresh_token", config.secret_name);
+
+    if let Some(proxy_url) = config.exchange_proxy_url.as_deref() {
+        let Some(gateway_token) = config.gateway_token.as_deref() else {
+            tracing::warn!(
+                "OAuth refresh proxy is configured, but no gateway auth token is available"
+            );
+            return false;
+        };
+
+        // In hosted mode, the configured exchange proxy owns the outbound token
+        // refresh and validation policy for the provider token_url. Direct-mode
+        // HTTPS/private-IP checks remain in place for self-hosted refreshes below.
+        let refresh_secret = match load_oauth_refresh_secret(store, user_id, &refresh_name).await {
+            Some(secret) => secret,
+            None => return false,
+        };
+        let token_response = match oauth_defaults::refresh_token_via_proxy(
+            oauth_defaults::ProxyRefreshTokenRequest {
+                proxy_url,
+                gateway_token,
+                token_url: &config.token_url,
+                client_id: &config.client_id,
+                client_secret: config.client_secret.as_deref(),
+                refresh_token: refresh_secret.expose(),
+                provider: config.provider.as_deref(),
+            },
+        )
+        .await
+        {
+            Ok(response) => response,
+            Err(error) => {
+                tracing::warn!(error = %error, "OAuth token refresh via proxy failed");
+                return false;
+            }
+        };
+
+        return persist_refreshed_oauth_tokens(
+            store,
+            user_id,
+            config,
+            &refresh_name,
+            token_response,
+        )
+        .await;
+    }
+
     // SSRF defense: token_url comes from the tool's capabilities file.
     if !config.token_url.starts_with("https://") {
         tracing::warn!(
@@ -1114,19 +1279,6 @@ async fn refresh_oauth_token(
         return false;
     }
 
-    let refresh_name = format!("{}_refresh_token", config.secret_name);
-    let refresh_secret = match store.get_decrypted(user_id, &refresh_name).await {
-        Ok(s) => s,
-        Err(e) => {
-            tracing::debug!(
-                secret_name = %refresh_name,
-                error = %e,
-                "No refresh token available, skipping token refresh"
-            );
-            return false;
-        }
-    };
-
     let client = match reqwest::Client::builder()
         .timeout(Duration::from_secs(15))
         .redirect(reqwest::redirect::Policy::none())
@@ -1139,6 +1291,10 @@ async fn refresh_oauth_token(
         }
     };
 
+    let refresh_secret = match load_oauth_refresh_secret(store, user_id, &refresh_name).await {
+        Some(secret) => secret,
+        None => return false,
+    };
     let mut params = vec![
         ("grant_type", "refresh_token".to_string()),
         ("refresh_token", refresh_secret.expose().to_string()),
@@ -1174,22 +1330,55 @@ async fn refresh_oauth_token(
             return false;
         }
     };
-
-    let new_access_token = match token_data.get("access_token").and_then(|v| v.as_str()) {
-        Some(t) => t,
+    let token_response = match token_data.get("access_token").and_then(|v| v.as_str()) {
+        Some(access_token) => oauth_defaults::OAuthTokenResponse {
+            access_token: access_token.to_string(),
+            refresh_token: token_data
+                .get("refresh_token")
+                .and_then(|v| v.as_str())
+                .map(str::to_string),
+            expires_in: token_data.get("expires_in").and_then(|v| v.as_u64()),
+        },
         None => {
             tracing::warn!("Token refresh response missing access_token field");
             return false;
         }
     };
 
-    // Store the new access token with expiry
+    persist_refreshed_oauth_tokens(store, user_id, config, &refresh_name, token_response).await
+}
+
+async fn load_oauth_refresh_secret(
+    store: &(dyn SecretsStore + Send + Sync),
+    user_id: &str,
+    refresh_name: &str,
+) -> Option<DecryptedSecret> {
+    match store.get_decrypted(user_id, refresh_name).await {
+        Ok(secret) => Some(secret),
+        Err(error) => {
+            tracing::debug!(
+                secret_name = %refresh_name,
+                error = %error,
+                "No refresh token available, skipping token refresh"
+            );
+            None
+        }
+    }
+}
+
+async fn persist_refreshed_oauth_tokens(
+    store: &(dyn SecretsStore + Send + Sync),
+    user_id: &str,
+    config: &OAuthRefreshConfig,
+    refresh_name: &str,
+    token_response: oauth_defaults::OAuthTokenResponse,
+) -> bool {
     let mut access_params =
-        crate::secrets::CreateSecretParams::new(&config.secret_name, new_access_token);
+        crate::secrets::CreateSecretParams::new(&config.secret_name, &token_response.access_token);
     if let Some(ref provider) = config.provider {
         access_params = access_params.with_provider(provider);
     }
-    if let Some(expires_in) = token_data.get("expires_in").and_then(|v| v.as_u64()) {
+    if let Some(expires_in) = token_response.expires_in {
         let expires_at = chrono::Utc::now() + chrono::Duration::seconds(expires_in as i64);
         access_params = access_params.with_expiry(expires_at);
     }
@@ -1199,10 +1388,8 @@ async fn refresh_oauth_token(
         return false;
     }
 
-    // Store rotated refresh token if the provider sent a new one
-    if let Some(new_refresh) = token_data.get("refresh_token").and_then(|v| v.as_str()) {
-        let mut refresh_params =
-            crate::secrets::CreateSecretParams::new(&refresh_name, new_refresh);
+    if let Some(new_refresh) = token_response.refresh_token.as_deref() {
+        let mut refresh_params = crate::secrets::CreateSecretParams::new(refresh_name, new_refresh);
         if let Some(ref provider) = config.provider {
             refresh_params = refresh_params.with_provider(provider);
         }
@@ -1551,9 +1738,18 @@ fn build_tool_usage_hint(tool_name: &str, schema: &serde_json::Value) -> String
 
 #[cfg(test)]
 mod tests {
+    use std::collections::HashMap;
+    use std::net::SocketAddr;
     use std::sync::{Arc, Mutex};
 
     use async_trait::async_trait;
+    use axum::extract::{Form, State};
+    use axum::http::HeaderMap;
+    use axum::routing::post;
+    use axum::{Json, Router};
+    use serde_json::json;
+    use tokio::net::TcpListener;
+    use tokio::sync::{Mutex as AsyncMutex, oneshot};
     use uuid::Uuid;
 
     use crate::context::JobContext;
@@ -1643,6 +1839,95 @@ mod tests {
         }
     }
 
+    #[derive(Clone, Debug, PartialEq, Eq)]
+    struct RecordedProxyRequest {
+        authorization: Option<String>,
+        form: HashMap<String, String>,
+    }
+
+    struct MockProxyServer {
+        addr: SocketAddr,
+        requests: Arc<AsyncMutex<Vec<RecordedProxyRequest>>>,
+        shutdown_tx: Option<oneshot::Sender<()>>,
+        server_task: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl MockProxyServer {
+        async fn start() -> Self {
+            async fn refresh_handler(
+                State(requests): State<Arc<AsyncMutex<Vec<RecordedProxyRequest>>>>,
+                headers: HeaderMap,
+                Form(form): Form<HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                requests.lock().await.push(RecordedProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(json!({
+                    "access_token": "mock-refreshed-access-token",
+                    "refresh_token": "mock-rotated-refresh-token",
+                    "expires_in": 3600
+                }))
+            }
+
+            let requests = Arc::new(AsyncMutex::new(Vec::new()));
+            let app = Router::new()
+                .route("/oauth/refresh", post(refresh_handler))
+                .with_state(Arc::clone(&requests));
+
+            let listener = TcpListener::bind("127.0.0.1:0")
+                .await
+                .expect("bind mock proxy");
+            let addr = listener.local_addr().expect("read mock proxy addr");
+            let (shutdown_tx, shutdown_rx) = oneshot::channel::<()>();
+            let server_task = tokio::spawn(async move {
+                let _ = axum::serve(listener, app)
+                    .with_graceful_shutdown(async {
+                        let _ = shutdown_rx.await;
+                    })
+                    .await;
+            });
+
+            Self {
+                addr,
+                requests,
+                shutdown_tx: Some(shutdown_tx),
+                server_task: Some(server_task),
+            }
+        }
+
+        fn base_url(&self) -> String {
+            format!("http://{}", self.addr)
+        }
+
+        async fn requests(&self) -> Vec<RecordedProxyRequest> {
+            self.requests.lock().await.clone()
+        }
+
+        async fn shutdown(mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                let _ = task.await;
+            }
+        }
+    }
+
+    impl Drop for MockProxyServer {
+        fn drop(&mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                task.abort();
+            }
+        }
+    }
+
     #[test]
     fn test_wrapper_creation() {
         // This test verifies the runtime can be created
@@ -1655,7 +1940,7 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn test_advertised_schema_stays_permissive_until_sidecar_override() {
+    async fn test_advertised_schema_auto_compacted_from_discovery() {
         let discovery_schema = serde_json::json!({
             "type": "object",
             "properties": {
@@ -1675,42 +1960,7 @@ mod tests {
         wrapper.schemas = super::WasmToolSchemas::new(discovery_schema.clone());
         wrapper.description = "Search documents".to_string();
 
-        // Advertised schema stays permissive; discovery holds the typed schema
-        assert_eq!(
-            wrapper.parameters_schema(),
-            serde_json::json!({
-                "type": "object",
-                "properties": {},
-                "additionalProperties": true
-            })
-        );
-        assert_eq!(wrapper.discovery_schema(), discovery_schema);
-
-        // Raw description is clean — no tool_info hint baked in
-        assert!(!wrapper.description().contains("tool_info"));
-
-        // But schema() composes the hint at display time when advertised is permissive
-        let schema = wrapper.schema();
-        assert!(
-            schema.description.contains("tool_info"),
-            "schema().description should contain tool_info hint: {}",
-            schema.description
-        );
-        assert!(
-            schema.description.contains("include_schema: true"),
-            "hint should mention include_schema: true: {}",
-            schema.description
-        );
-
-        // After sidecar override, both schemas match and hint disappears
-        let wrapper = wrapper.with_schema(serde_json::json!({
-            "type": "object",
-            "properties": {
-                "query": { "type": "string" }
-            },
-            "required": ["query"]
-        }));
-
+        // Advertised schema is auto-compacted: keeps required props, drops optional
         assert_eq!(
             wrapper.parameters_schema(),
             serde_json::json!({
@@ -1718,20 +1968,143 @@ mod tests {
                 "properties": {
                     "query": { "type": "string" }
                 },
-                "required": ["query"]
+                "required": ["query"],
+                "additionalProperties": true
             })
         );
-        assert_eq!(wrapper.discovery_schema(), wrapper.parameters_schema());
+        // Discovery retains the full schema
+        assert_eq!(wrapper.discovery_schema(), discovery_schema);
 
-        // With typed schema, schema() should NOT include tool_info hint
+        // Compacted schema has typed properties, so no tool_info hint needed
         let schema = wrapper.schema();
         assert!(
             !schema.description.contains("tool_info"),
-            "schema().description should not contain tool_info hint when typed: {}",
+            "schema().description should not contain tool_info hint when auto-compacted: {}",
             schema.description
         );
     }
 
+    #[test]
+    fn test_compact_schema_keeps_required_and_enum_properties() {
+        let schema = serde_json::json!({
+            "type": "object",
+            "properties": {
+                "action": {
+                    "type": "string",
+                    "enum": ["list", "get", "create"],
+                    "description": "The operation"
+                },
+                "query": { "type": "string" },
+                "limit": { "type": "integer" },
+                "format": {
+                    "type": "string",
+                    "enum": ["json", "csv"]
+                }
+            },
+            "required": ["action"]
+        });
+
+        let compacted = super::WasmToolSchemas::compact_schema(&schema);
+        let props = compacted["properties"].as_object().unwrap();
+
+        // action: required + enum → kept
+        assert!(props.contains_key("action"));
+        // format: has enum → kept
+        assert!(props.contains_key("format"));
+        // query: not required, no enum → dropped
+        assert!(!props.contains_key("query"));
+        // limit: not required, no enum → dropped
+        assert!(!props.contains_key("limit"));
+        // additionalProperties lets the LLM still pass dropped props
+        assert_eq!(compacted["additionalProperties"], true);
+        assert_eq!(compacted["required"], serde_json::json!(["action"]));
+    }
+
+    #[test]
+    fn test_compact_schema_falls_back_to_permissive_when_empty() {
+        // No required, no enum → permissive fallback
+        let schema = serde_json::json!({
+            "type": "object",
+            "properties": {
+                "query": { "type": "string" },
+                "limit": { "type": "integer" }
+            }
+        });
+
+        let compacted = super::WasmToolSchemas::compact_schema(&schema);
+        assert!(compacted["properties"].as_object().unwrap().is_empty());
+    }
+
+    #[test]
+    fn test_compact_schema_handles_no_properties() {
+        let schema = serde_json::json!({ "type": "object" });
+        let compacted = super::WasmToolSchemas::compact_schema(&schema);
+        assert!(compacted["properties"].as_object().unwrap().is_empty());
+    }
+
+    #[test]
+    fn test_compact_schema_handles_oneof_variants() {
+        // GitHub-style schema: oneOf with no top-level properties, const per variant
+        let schema = serde_json::json!({
+            "type": "object",
+            "required": ["action"],
+            "oneOf": [
+                {
+                    "properties": {
+                        "action": { "const": "get_repo" },
+                        "owner": { "type": "string" },
+                        "repo": { "type": "string" }
+                    },
+                    "required": ["action", "owner", "repo"]
+                },
+                {
+                    "properties": {
+                        "action": { "const": "list_issues" },
+                        "owner": { "type": "string" },
+                        "repo": { "type": "string" },
+                        "state": { "type": "string", "enum": ["open", "closed", "all"] }
+                    },
+                    "required": ["action", "owner", "repo"]
+                }
+            ]
+        });
+
+        let compacted = super::WasmToolSchemas::compact_schema(&schema);
+        let props = compacted["properties"].as_object().unwrap();
+
+        // action: required + const values merged into enum → kept
+        let action = &props["action"];
+        assert!(
+            action.get("enum").is_some(),
+            "action const values should be merged into enum: {action}"
+        );
+        let action_enum = action["enum"].as_array().unwrap();
+        assert!(
+            action_enum.contains(&serde_json::json!("get_repo")),
+            "enum should contain get_repo"
+        );
+        assert!(
+            action_enum.contains(&serde_json::json!("list_issues")),
+            "enum should contain list_issues"
+        );
+        assert!(
+            action.get("const").is_none(),
+            "const should be removed after merging into enum"
+        );
+
+        // state: has enum → kept
+        assert!(
+            props.contains_key("state"),
+            "state should be kept (has enum)"
+        );
+        // owner/repo: not in top-level required, no enum → intentionally dropped
+        // (variant-level required is omitted; discoverable via tool_info)
+        assert!(!props.contains_key("owner"), "owner should be dropped");
+        assert!(!props.contains_key("repo"), "repo should be dropped");
+        assert_eq!(compacted["additionalProperties"], true);
+        assert_eq!(compacted["required"], serde_json::json!(["action"]));
+    }
+
     #[test]
     fn test_capabilities_default() {
         let caps = Capabilities::default();
@@ -1893,8 +2266,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_bearer() {
-        use std::collections::HashMap;
-
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
@@ -1940,8 +2311,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_owner_scope_bearer() {
-        use std::collections::HashMap;
-
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
@@ -1987,8 +2356,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_execute_resolves_host_credentials_from_owner_scope_context() {
-        use std::collections::HashMap;
-
         use crate::secrets::{CredentialLocation, CredentialMapping};
         use crate::tools::wasm::capabilities::HttpCapability;
 
@@ -2038,8 +2405,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_missing_secret() {
-        use std::collections::HashMap;
-
         use crate::secrets::{CredentialLocation, CredentialMapping};
         use crate::tools::wasm::capabilities::HttpCapability;
         use crate::tools::wasm::wrapper::resolve_host_credentials;
@@ -2071,8 +2436,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_skips_refresh_when_not_expired() {
-        use std::collections::HashMap;
-
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
@@ -2114,6 +2477,8 @@ mod tests {
             token_url: "https://oauth2.googleapis.com/token".to_string(),
             client_id: TEST_OAUTH_CLIENT_ID.to_string(),
             client_secret: Some(TEST_OAUTH_CLIENT_SECRET.to_string()),
+            exchange_proxy_url: None,
+            gateway_token: None,
             secret_name: "google_oauth_token".to_string(),
             provider: Some("google".to_string()),
         };
@@ -2130,8 +2495,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_skips_refresh_no_config() {
-        use std::collections::HashMap;
-
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
@@ -2175,8 +2538,6 @@ mod tests {
 
     #[tokio::test]
     async fn test_resolve_host_credentials_skips_refresh_no_expires_at() {
-        use std::collections::HashMap;
-
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
@@ -2216,6 +2577,8 @@ mod tests {
             token_url: "https://oauth2.googleapis.com/token".to_string(),
             client_id: TEST_OAUTH_CLIENT_ID.to_string(),
             client_secret: Some(TEST_OAUTH_CLIENT_SECRET.to_string()),
+            exchange_proxy_url: None,
+            gateway_token: None,
             secret_name: "google_oauth_token".to_string(),
             provider: Some("google".to_string()),
         };
@@ -2230,6 +2593,249 @@ mod tests {
         );
     }
 
+    #[tokio::test]
+    async fn test_resolve_host_credentials_refreshes_via_proxy_without_direct_token_url_validation()
+    {
+        use crate::secrets::{
+            CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
+        };
+        use crate::tools::wasm::capabilities::HttpCapability;
+        use crate::tools::wasm::wrapper::{OAuthRefreshConfig, resolve_host_credentials};
+
+        let proxy = MockProxyServer::start().await;
+        let store = test_secrets_store();
+
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token", "expired-access-token")
+                    .with_expiry(chrono::Utc::now() - chrono::Duration::hours(1)),
+            )
+            .await
+            .unwrap();
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token_refresh_token", "stored-refresh-token"),
+            )
+            .await
+            .unwrap();
+
+        let mut credentials = HashMap::new();
+        credentials.insert(
+            "google_oauth_token".to_string(),
+            CredentialMapping {
+                secret_name: "google_oauth_token".to_string(),
+                location: CredentialLocation::AuthorizationBearer,
+                host_patterns: vec!["www.googleapis.com".to_string()],
+            },
+        );
+
+        let caps = Capabilities {
+            http: Some(HttpCapability {
+                credentials,
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let oauth_config = OAuthRefreshConfig {
+            token_url: "http://127.0.0.1:9/provider-token-endpoint".to_string(),
+            client_id: "hosted-google-client-id".to_string(),
+            client_secret: None,
+            exchange_proxy_url: Some(proxy.base_url()),
+            gateway_token: Some("gateway-test-token".to_string()),
+            secret_name: "google_oauth_token".to_string(),
+            provider: Some("google".to_string()),
+        };
+
+        let resolved =
+            resolve_host_credentials(&caps, Some(&store), "user1", Some(&oauth_config)).await;
+        assert_eq!(resolved.len(), 1);
+        assert_eq!(
+            resolved[0].headers.get("Authorization"),
+            Some(&"Bearer mock-refreshed-access-token".to_string())
+        );
+
+        let access_secret = store.get("user1", "google_oauth_token").await.unwrap();
+        assert!(
+            access_secret
+                .expires_at
+                .expect("refreshed access token expiry")
+                > chrono::Utc::now()
+        );
+        let access_value = store
+            .get_decrypted("user1", "google_oauth_token")
+            .await
+            .unwrap();
+        assert_eq!(access_value.expose(), "mock-refreshed-access-token");
+
+        let refresh_value = store
+            .get_decrypted("user1", "google_oauth_token_refresh_token")
+            .await
+            .unwrap();
+        assert_eq!(refresh_value.expose(), "mock-rotated-refresh-token");
+
+        let requests = proxy.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer gateway-test-token")
+        );
+        assert_eq!(
+            requests[0].form.get("client_id").map(String::as_str),
+            Some("hosted-google-client-id")
+        );
+        assert_eq!(
+            requests[0].form.get("token_url").map(String::as_str),
+            Some("http://127.0.0.1:9/provider-token-endpoint")
+        );
+        assert_eq!(
+            requests[0].form.get("refresh_token").map(String::as_str),
+            Some("stored-refresh-token")
+        );
+        assert_eq!(
+            requests[0].form.get("provider").map(String::as_str),
+            Some("google")
+        );
+        assert!(!requests[0].form.contains_key("client_secret"));
+
+        proxy.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_resolve_host_credentials_skips_refresh_token_lookup_without_gateway_token() {
+        use crate::secrets::{
+            CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
+        };
+        use crate::tools::wasm::capabilities::HttpCapability;
+        use crate::tools::wasm::wrapper::{OAuthRefreshConfig, resolve_host_credentials};
+
+        let store = RecordingSecretsStore::new();
+
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token", "expired-access-token")
+                    .with_expiry(chrono::Utc::now() - chrono::Duration::hours(1)),
+            )
+            .await
+            .unwrap();
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token_refresh_token", "stored-refresh-token"),
+            )
+            .await
+            .unwrap();
+
+        let mut credentials = HashMap::new();
+        credentials.insert(
+            "google_oauth_token".to_string(),
+            CredentialMapping {
+                secret_name: "google_oauth_token".to_string(),
+                location: CredentialLocation::AuthorizationBearer,
+                host_patterns: vec!["www.googleapis.com".to_string()],
+            },
+        );
+
+        let caps = Capabilities {
+            http: Some(HttpCapability {
+                credentials,
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let oauth_config = OAuthRefreshConfig {
+            token_url: "https://oauth2.googleapis.com/token".to_string(),
+            client_id: "hosted-google-client-id".to_string(),
+            client_secret: None,
+            exchange_proxy_url: Some("https://compose-api.example.com".to_string()),
+            gateway_token: None,
+            secret_name: "google_oauth_token".to_string(),
+            provider: Some("google".to_string()),
+        };
+
+        let resolved =
+            resolve_host_credentials(&caps, Some(&store), "user1", Some(&oauth_config)).await;
+        assert!(resolved.is_empty());
+
+        let lookups = store.decrypted_lookups();
+        assert!(lookups.contains(&("user1".to_string(), "google_oauth_token".to_string())));
+        assert!(!lookups.contains(&(
+            "user1".to_string(),
+            "google_oauth_token_refresh_token".to_string(),
+        )));
+    }
+
+    #[tokio::test]
+    async fn test_resolve_host_credentials_skips_refresh_token_lookup_for_invalid_direct_token_url()
+    {
+        use crate::secrets::{
+            CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
+        };
+        use crate::tools::wasm::capabilities::HttpCapability;
+        use crate::tools::wasm::wrapper::{OAuthRefreshConfig, resolve_host_credentials};
+
+        let store = RecordingSecretsStore::new();
+
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token", "expired-access-token")
+                    .with_expiry(chrono::Utc::now() - chrono::Duration::hours(1)),
+            )
+            .await
+            .unwrap();
+        store
+            .create(
+                "user1",
+                CreateSecretParams::new("google_oauth_token_refresh_token", "stored-refresh-token"),
+            )
+            .await
+            .unwrap();
+
+        let mut credentials = HashMap::new();
+        credentials.insert(
+            "google_oauth_token".to_string(),
+            CredentialMapping {
+                secret_name: "google_oauth_token".to_string(),
+                location: CredentialLocation::AuthorizationBearer,
+                host_patterns: vec!["www.googleapis.com".to_string()],
+            },
+        );
+
+        let caps = Capabilities {
+            http: Some(HttpCapability {
+                credentials,
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let oauth_config = OAuthRefreshConfig {
+            token_url: "http://127.0.0.1:9/provider-token-endpoint".to_string(),
+            client_id: TEST_OAUTH_CLIENT_ID.to_string(),
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET.to_string()),
+            exchange_proxy_url: None,
+            gateway_token: None,
+            secret_name: "google_oauth_token".to_string(),
+            provider: Some("google".to_string()),
+        };
+
+        let resolved =
+            resolve_host_credentials(&caps, Some(&store), "user1", Some(&oauth_config)).await;
+        assert!(resolved.is_empty());
+
+        let lookups = store.decrypted_lookups();
+        assert!(lookups.contains(&("user1".to_string(), "google_oauth_token".to_string())));
+        assert!(!lookups.contains(&(
+            "user1".to_string(),
+            "google_oauth_token_refresh_token".to_string(),
+        )));
+    }
+
     #[test]
     fn test_is_private_ip_v4() {
         use std::net::IpAddr;

src/tunnel/cloudflare.rs

@@ -111,10 +111,23 @@ impl Tunnel for CloudflareTunnel {
             }
         }
 
-        // Drain stderr in the background to prevent SIGPIPE/buffer stalls.
-        tokio::spawn(async move { while let Ok(Some(_)) = reader.next_line().await {} });
+        if let Ok(mut guard) = self.url.write() {
+            *guard = Some(public_url.clone());
+        }
 
-        // Drain stdout silently.
+        // We took ownership of cloudflared's stderr pipe above to parse the URL.
+        // cloudflared continues writing logs for its entire lifetime. If we drop
+        // the reader, the pipe closes and cloudflared gets SIGPIPE on its next
+        // write. We can't just store the reader without reading — the OS pipe
+        // buffer fills up and cloudflared blocks. So we drain it in a background
+        // task. The task exits naturally when cloudflared is killed (EOF).
+        let drain_handle = tokio::spawn(async move {
+            while let Ok(Some(line)) = reader.next_line().await {
+                tracing::trace!("cloudflared: {line}");
+            }
+        });
+
+        // Drain stdout silently to prevent SIGPIPE/buffer stalls.
         if let Some(stdout) = stdout {
             tokio::spawn(async move {
                 let mut out_reader = tokio::io::BufReader::new(stdout).lines();
@@ -122,12 +135,11 @@ impl Tunnel for CloudflareTunnel {
             });
         }
 
-        if let Ok(mut guard) = self.url.write() {
-            *guard = Some(public_url.clone());
-        }
-
         let mut guard = self.proc.lock().await;
-        *guard = Some(TunnelProcess { child });
+        *guard = Some(TunnelProcess {
+            child,
+            _pipe_drain: Some(drain_handle),
+        });
 
         Ok(public_url)
     }

src/tunnel/custom.rs

@@ -73,6 +73,7 @@ impl Tunnel for CustomTunnel {
         let stderr = child.stderr.take();
 
         let mut public_url = format!("http://{local_host}:{local_port}");
+        let mut drain_handle: Option<tokio::task::JoinHandle<()>> = None;
 
         if self.url_pattern.is_some()
             && let Some(stdout) = stdout
@@ -103,17 +104,26 @@ impl Tunnel for CustomTunnel {
                     Err(_) => {}
                 }
             }
-            // Drain remaining stdout to prevent SIGPIPE/buffer stalls.
-            tokio::spawn(async move { while let Ok(Some(_)) = reader.next_line().await {} });
+            // We took ownership of the process's stdout pipe above to parse the
+            // URL. The process may continue writing to stdout for its lifetime.
+            // If we drop the reader, the pipe closes and the process gets SIGPIPE.
+            // We can't just store the reader without reading — the OS pipe buffer
+            // fills up and the process blocks. So we drain it in a background task.
+            // The task exits naturally when the process is killed (EOF).
+            drain_handle = Some(tokio::spawn(async move {
+                while let Ok(Some(line)) = reader.next_line().await {
+                    tracing::trace!("custom-tunnel: {line}");
+                }
+            }));
         } else if let Some(stdout) = stdout {
-            // No url_pattern: still drain stdout to prevent pipe stalls.
+            // No url_pattern: still drain stdout to prevent SIGPIPE/buffer stalls.
             tokio::spawn(async move {
                 let mut reader = tokio::io::BufReader::new(stdout).lines();
                 while let Ok(Some(_)) = reader.next_line().await {}
             });
         }
 
-        // Drain stderr silently.
+        // Drain stderr to prevent SIGPIPE/buffer stalls.
         if let Some(stderr) = stderr {
             tokio::spawn(async move {
                 let mut reader = tokio::io::BufReader::new(stderr).lines();
@@ -126,7 +136,10 @@ impl Tunnel for CustomTunnel {
         }
 
         let mut guard = self.proc.lock().await;
-        *guard = Some(TunnelProcess { child });
+        *guard = Some(TunnelProcess {
+            child,
+            _pipe_drain: drain_handle,
+        });
 
         Ok(public_url)
     }

src/tunnel/mod.rs

@@ -66,6 +66,10 @@ pub trait Tunnel: Send + Sync {
 /// Wraps a spawned tunnel child process.
 pub(crate) struct TunnelProcess {
     pub child: tokio::process::Child,
+    /// Background task that drains the process's output pipe (stdout or stderr).
+    /// Must stay alive or the process dies (SIGPIPE from closed pipe) or hangs
+    /// (OS pipe buffer fills up, blocking the process's writes).
+    pub _pipe_drain: Option<tokio::task::JoinHandle<()>>,
 }
 
 pub(crate) type SharedProcess = Arc<Mutex<Option<TunnelProcess>>>;
@@ -182,6 +186,22 @@ pub fn create_tunnel(config: &TunnelProviderConfig) -> Result<Option<Box<dyn Tun
 
 // ── Managed tunnel startup ───────────────────────────────────────
 
+/// Determine which local address the tunnel should forward traffic to.
+///
+/// Prefers the webhook server (`HTTP_PORT`) since that's where webhook routes
+/// (Telegram, etc.) are served. Falls back to the gateway port if configured,
+/// otherwise defaults to 0.0.0.0:8080 (the same fallback the webhook server
+/// uses in main.rs when no HTTP config is present).
+fn resolve_tunnel_target(channels: &crate::config::ChannelsConfig) -> (&str, u16) {
+    if let Some(ref http) = channels.http {
+        return (http.host.as_str(), http.port);
+    }
+    if let Some(ref gw) = channels.gateway {
+        return (gw.host.as_str(), gw.port);
+    }
+    ("0.0.0.0", 8080)
+}
+
 /// Start a managed tunnel if configured and no static URL is already set.
 ///
 /// Returns the (potentially mutated) config with `tunnel.public_url` set,
@@ -201,28 +221,17 @@ pub async fn start_managed_tunnel(
         return (config, None);
     };
 
-    let gateway_port = config
-        .channels
-        .gateway
-        .as_ref()
-        .map(|g| g.port)
-        .unwrap_or(3000);
-    let gateway_host = config
-        .channels
-        .gateway
-        .as_ref()
-        .map(|g| g.host.as_str())
-        .unwrap_or("127.0.0.1");
+    let (tunnel_host, tunnel_port) = resolve_tunnel_target(&config.channels);
 
     match create_tunnel(provider_config) {
         Ok(Some(tunnel)) => {
             tracing::debug!(
                 "Starting {} tunnel on {}:{}...",
                 tunnel.name(),
-                gateway_host,
-                gateway_port
+                tunnel_host,
+                tunnel_port
             );
-            match tunnel.start(gateway_host, gateway_port).await {
+            match tunnel.start(tunnel_host, tunnel_port).await {
                 Ok(url) => {
                     tracing::debug!("Tunnel started: {}", url);
                     config.tunnel.public_url = Some(url);
@@ -383,10 +392,111 @@ mod tests {
 
         {
             let mut guard = proc.lock().await;
-            *guard = Some(TunnelProcess { child });
+            *guard = Some(TunnelProcess {
+                child,
+                _pipe_drain: None,
+            });
         }
 
         kill_shared(&proc).await.unwrap();
         assert!(proc.lock().await.is_none());
     }
+
+    // ── Port selection regression tests ──────────────────────────────
+
+    fn base_channels() -> crate::config::ChannelsConfig {
+        crate::config::ChannelsConfig {
+            cli: crate::config::CliConfig { enabled: false },
+            http: None,
+            gateway: None,
+            signal: None,
+            wasm_channels_dir: std::env::temp_dir().join("ironclaw-test-channels"),
+            wasm_channels_enabled: false,
+            wasm_channel_owner_ids: std::collections::HashMap::new(),
+        }
+    }
+
+    fn channels_with_http(host: &str, port: u16) -> crate::config::ChannelsConfig {
+        let mut c = base_channels();
+        c.http = Some(crate::config::HttpConfig {
+            host: host.to_string(),
+            port,
+            webhook_secret: None,
+            user_id: "test".to_string(),
+        });
+        c.gateway = Some(crate::config::GatewayConfig {
+            host: "127.0.0.1".to_string(),
+            port: 3000,
+            auth_token: None,
+            user_id: "test".to_string(),
+            workspace_read_scopes: Vec::new(),
+            memory_layers: Vec::new(),
+            user_tokens: None,
+        });
+        c
+    }
+
+    fn channels_gateway_only(host: &str, port: u16) -> crate::config::ChannelsConfig {
+        let mut c = base_channels();
+        c.gateway = Some(crate::config::GatewayConfig {
+            host: host.to_string(),
+            port,
+            auth_token: None,
+            user_id: "test".to_string(),
+            workspace_read_scopes: Vec::new(),
+            memory_layers: Vec::new(),
+            user_tokens: None,
+        });
+        c
+    }
+
+    fn channels_neither() -> crate::config::ChannelsConfig {
+        base_channels()
+    }
+
+    #[test]
+    fn tunnel_target_prefers_http_port() {
+        let channels = channels_with_http("0.0.0.0", 8080);
+        let (host, port) = resolve_tunnel_target(&channels);
+        assert_eq!(host, "0.0.0.0"); // safety: test-only
+        assert_eq!(port, 8080); // safety: test-only
+    }
+
+    #[test]
+    fn tunnel_target_falls_back_to_gateway() {
+        let channels = channels_gateway_only("10.0.0.1", 4000);
+        let (host, port) = resolve_tunnel_target(&channels);
+        assert_eq!(host, "10.0.0.1"); // safety: test-only
+        assert_eq!(port, 4000); // safety: test-only
+    }
+
+    #[test]
+    fn tunnel_target_defaults_to_webhook_fallback() {
+        let channels = channels_neither();
+        let (host, port) = resolve_tunnel_target(&channels);
+        // Matches the webhook server's hardcoded fallback in main.rs
+        assert_eq!(host, "0.0.0.0"); // safety: test-only
+        assert_eq!(port, 8080); // safety: test-only
+    }
+
+    #[test]
+    fn tunnel_target_http_takes_priority_over_gateway() {
+        let channels = channels_with_http("192.168.1.1", 9090);
+        let (host, port) = resolve_tunnel_target(&channels);
+        // Should use HTTP config, not gateway's 127.0.0.1:3000
+        assert_eq!(host, "192.168.1.1"); // safety: test-only
+        assert_eq!(port, 9090); // safety: test-only
+    }
+
+    #[test]
+    fn tunnel_target_no_http_no_gateway_matches_webhook_fallback() {
+        // When HTTP_PORT is not set and gateway is not configured (e.g. WASM
+        // channels exist but no explicit HTTP config), the webhook server in
+        // main.rs binds to 0.0.0.0:8080 as a hardcoded fallback. The tunnel
+        // must target the same address so webhook traffic reaches the right
+        // server.
+        let channels = channels_neither();
+        let (host, port) = resolve_tunnel_target(&channels);
+        assert_eq!((host, port), ("0.0.0.0", 8080)); // safety: test-only
+    }
 }

src/tunnel/ngrok.rs

@@ -110,12 +110,24 @@ impl Tunnel for NgrokTunnel {
             }
         }
 
-        // Drain stdout silently — ngrok only emits low-level connection events
-        // to stdout; the pipe must be consumed to prevent SIGPIPE/buffer stalls.
-        tokio::spawn(async move { while let Ok(Some(_)) = reader.next_line().await {} });
+        if let Ok(mut guard) = self.url.write() {
+            *guard = Some(public_url.clone());
+        }
 
-        // Drain stderr silently — with --log stdout all meaningful output goes
-        // to stdout; stderr only needs to be consumed to prevent pipe stalls.
+        // We took ownership of ngrok's stdout pipe above to parse the URL.
+        // ngrok continues writing logs to stdout for its entire lifetime.
+        // If we drop the reader, the pipe closes and ngrok gets SIGPIPE on
+        // its next write → process dies. We can't just store the reader
+        // without reading — the OS pipe buffer (~64KB) fills up and ngrok
+        // blocks. So we drain it in a background task. The task exits
+        // naturally when ngrok is killed (EOF on the pipe).
+        let drain_handle = tokio::spawn(async move {
+            while let Ok(Some(line)) = reader.next_line().await {
+                tracing::trace!("ngrok: {line}");
+            }
+        });
+
+        // Drain stderr silently to prevent SIGPIPE/buffer stalls.
         if let Some(stderr) = stderr {
             tokio::spawn(async move {
                 let mut err_reader = tokio::io::BufReader::new(stderr).lines();
@@ -123,12 +135,11 @@ impl Tunnel for NgrokTunnel {
             });
         }
 
-        if let Ok(mut guard) = self.url.write() {
-            *guard = Some(public_url.clone());
-        }
-
         let mut guard = self.proc.lock().await;
-        *guard = Some(TunnelProcess { child });
+        *guard = Some(TunnelProcess {
+            child,
+            _pipe_drain: Some(drain_handle),
+        });
 
         Ok(public_url)
     }

src/worker/job.rs

@@ -48,8 +48,8 @@ pub struct WorkerDeps {
     pub hooks: Arc<HookRegistry>,
     pub timeout: Duration,
     pub use_planning: bool,
-    /// SSE broadcast sender for live job event streaming to the web gateway.
-    pub sse_tx: Option<tokio::sync::broadcast::Sender<SseEvent>>,
+    /// SSE manager for live job event streaming to the web gateway.
+    pub sse_tx: Option<Arc<crate::channels::web::sse::SseManager>>,
     /// Approval context for tool execution. When `None`, all non-`Never` tools are
     /// blocked (legacy behavior). When `Some`, the context determines which tools
     /// are pre-approved for autonomous execution.
@@ -138,7 +138,7 @@ impl Worker {
         }
 
         // Broadcast SSE for live web UI updates
-        if let Some(ref tx) = self.deps.sse_tx {
+        if let Some(ref sse) = self.deps.sse_tx {
             let job_id_str = job_id.to_string();
             let event = match event_type {
                 "message" => Some(SseEvent::JobMessage {
@@ -203,7 +203,7 @@ impl Worker {
                 _ => None,
             };
             if let Some(event) = event {
-                let _ = tx.send(event);
+                sse.broadcast(event);
             }
         }
     }

src/workspace/embedding_cache.rs

@@ -3,14 +3,13 @@
 //! Avoids redundant HTTP calls for identical texts by caching embeddings
 //! in memory keyed by `SHA-256(model_name + "\0" + text)`.
 //!
-//! Follows the same cache pattern as `llm::response_cache::CachedProvider`:
-//! `HashMap` + `last_accessed` tracking + manual LRU eviction.
+//! Uses `lru::LruCache` for O(1) insertion, lookup, and eviction.
 
-use std::collections::HashMap;
+use std::num::NonZeroUsize;
 use std::sync::{Arc, Mutex};
-use std::time::Instant;
 
 use async_trait::async_trait;
+use lru::LruCache;
 use sha2::{Digest, Sha256};
 
 use crate::workspace::embeddings::{EmbeddingError, EmbeddingProvider};
@@ -22,8 +21,7 @@ pub struct EmbeddingCacheConfig {
     ///
     /// Approximate raw embedding payload: `max_entries × dimension × 4 bytes`.
     /// At 10,000 entries × 1536 floats ≈ 58 MB (payload only; actual memory
-    /// is higher due to HashMap buckets, `[u8; 32]` hash keys, `Vec`/`Instant`
-    /// per-entry overhead).
+    /// is higher due to per-entry overhead in the linked-list LRU).
     pub max_entries: usize,
 }
 
@@ -35,11 +33,6 @@ impl Default for EmbeddingCacheConfig {
     }
 }
 
-struct CacheEntry {
-    embedding: Vec<f32>,
-    last_accessed: Instant,
-}
-
 /// Embedding provider wrapper that caches results in memory.
 ///
 /// Thread-safe via `std::sync::Mutex`. The lock is **never held**
@@ -47,8 +40,7 @@ struct CacheEntry {
 /// so a synchronous mutex is cheaper than `tokio::sync::Mutex`.
 pub struct CachedEmbeddingProvider {
     inner: Arc<dyn EmbeddingProvider>,
-    cache: Mutex<HashMap<[u8; 32], CacheEntry>>,
-    config: EmbeddingCacheConfig,
+    cache: Mutex<LruCache<[u8; 32], Vec<f32>>>,
 }
 
 impl CachedEmbeddingProvider {
@@ -56,19 +48,18 @@ impl CachedEmbeddingProvider {
     ///
     /// `config.max_entries` is clamped to at least 1.
     pub fn new(inner: Arc<dyn EmbeddingProvider>, config: EmbeddingCacheConfig) -> Self {
-        let config = EmbeddingCacheConfig {
-            max_entries: config.max_entries.max(1),
-        };
-        if config.max_entries > 100_000 {
+        let max_entries = config.max_entries.max(1);
+        if max_entries > 100_000 {
             tracing::warn!(
-                max_entries = config.max_entries,
+                max_entries,
                 "Embedding cache size exceeds 100,000 entries; memory usage may be significant"
             );
         }
+        // safety: max_entries >= 1 due to .max(1) above
+        let cap = NonZeroUsize::new(max_entries).expect("clamped to >= 1"); // safety: always >= 1
         Self {
             inner,
-            cache: Mutex::new(HashMap::with_capacity(config.max_entries.min(1024))),
-            config,
+            cache: Mutex::new(LruCache::new(cap)),
         }
     }
 
@@ -100,49 +91,6 @@ impl CachedEmbeddingProvider {
         hasher.update(text.as_bytes());
         hasher.finalize().into()
     }
-
-    /// Evict the least-recently-used entry if at capacity (single-entry path).
-    // TODO: O(n) scan per eviction. If max_entries grows large, switch to
-    // an ordered data structure (e.g. `IndexMap` with swap_remove, or a
-    // linked-list LRU like the `lru` crate).
-    fn evict_lru(cache: &mut HashMap<[u8; 32], CacheEntry>, max_entries: usize) {
-        while cache.len() >= max_entries {
-            let oldest_key = cache
-                .iter()
-                .min_by_key(|(_, entry)| entry.last_accessed)
-                .map(|(k, _)| *k);
-
-            if let Some(k) = oldest_key {
-                cache.remove(&k);
-            } else {
-                break;
-            }
-        }
-    }
-
-    /// Evict the `k` oldest entries in O(n) average time via partial selection.
-    ///
-    /// Used by `embed_batch` to avoid the O(n×m) cost of calling
-    /// `evict_lru` per insert.
-    fn evict_k_oldest(cache: &mut HashMap<[u8; 32], CacheEntry>, k: usize) {
-        if k == 0 || cache.is_empty() {
-            return;
-        }
-        if k >= cache.len() {
-            cache.clear();
-            return;
-        }
-        // Partial selection: find the k oldest in O(n) average via
-        // select_nth_unstable_by_key, then remove the first k entries.
-        let mut entries: Vec<([u8; 32], Instant)> = cache
-            .iter()
-            .map(|(key, entry)| (*key, entry.last_accessed))
-            .collect();
-        entries.select_nth_unstable_by_key(k - 1, |(_, t)| *t);
-        for (key, _) in entries.into_iter().take(k) {
-            cache.remove(&key);
-        }
-    }
 }
 
 #[async_trait]
@@ -162,39 +110,32 @@ impl EmbeddingProvider for CachedEmbeddingProvider {
     async fn embed(&self, text: &str) -> Result<Vec<f32>, EmbeddingError> {
         let key = self.cache_key(text);
 
-        // Check cache (short critical section)
+        // Check cache (short critical section). LruCache::get promotes the
+        // entry to most-recently-used automatically.
         {
             let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
-            if let Some(entry) = guard.get_mut(&key) {
-                entry.last_accessed = Instant::now();
+            if let Some(embedding) = guard.get(&key) {
                 tracing::trace!("embedding cache hit");
-                return Ok(entry.embedding.clone());
+                return Ok(embedding.clone());
             }
         }
         // Lock released before HTTP call.
         // NOTE: Thundering herd — multiple concurrent callers with the same
         // uncached key will each call the inner provider. This is acceptable:
-        // embeddings are idempotent and the last writer wins in the HashMap.
+        // embeddings are idempotent and the last writer wins in the LruCache.
 
         let embedding = self.inner.embed(text).await?;
 
-        // Store result. Re-check under lock: another concurrent caller may
-        // have inserted this key while the lock was released for the HTTP call.
+        // Store result under lock. Re-check first: another concurrent caller
+        // may have already cached this key while the lock was released.
         {
             let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
-            if let Some(entry) = guard.get_mut(&key) {
-                // Thundering herd — another caller already cached it.
-                // Just touch timestamp; skip the clone.
-                entry.last_accessed = Instant::now();
+            if guard.get(&key).is_some() {
+                // Thundering herd — another caller beat us. LruCache::get
+                // already promoted it to most-recently-used; skip the clone.
+                tracing::trace!("embedding cache: concurrent insert, skipping clone");
             } else {
-                Self::evict_lru(&mut guard, self.config.max_entries);
-                guard.insert(
-                    key,
-                    CacheEntry {
-                        embedding: embedding.clone(),
-                        last_accessed: Instant::now(),
-                    },
-                );
+                guard.push(key, embedding.clone());
             }
         }
 
@@ -214,11 +155,9 @@ impl EmbeddingProvider for CachedEmbeddingProvider {
 
         {
             let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
-            let now = Instant::now();
             for (i, key) in keys.iter().enumerate() {
-                if let Some(entry) = guard.get_mut(key) {
-                    entry.last_accessed = now;
-                    results[i] = Some(entry.embedding.clone());
+                if let Some(embedding) = guard.get(key) {
+                    results[i] = Some(embedding.clone());
                 } else {
                     miss_indices.push(i);
                 }
@@ -228,7 +167,6 @@ impl EmbeddingProvider for CachedEmbeddingProvider {
 
         if miss_indices.is_empty() {
             tracing::trace!(count = texts.len(), "embedding batch: all cache hits");
-            // All slots populated from cache hits
             return results
                 .into_iter()
                 .enumerate()
@@ -260,29 +198,18 @@ impl EmbeddingProvider for CachedEmbeddingProvider {
             "embedding batch: partial cache"
         );
 
-        // Cache FIRST (clone only the cacheable subset), then move originals
-        // into results. This avoids cloning capacity-skipped embeddings entirely.
+        // Cache only the last `cap` new embeddings — caching more than the
+        // cache capacity wastes clone work on entries that are immediately evicted.
         {
             let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
-            let cacheable = miss_indices.len().min(self.config.max_entries);
-            let skip = miss_indices.len() - cacheable;
-            let need_to_evict = (guard.len() + cacheable).saturating_sub(self.config.max_entries);
-            if need_to_evict > 0 {
-                Self::evict_k_oldest(&mut guard, need_to_evict);
-            }
-            let now = Instant::now();
+            let cap = guard.cap().get();
+            let skip = miss_indices.len().saturating_sub(cap);
             for (&orig_idx, emb) in miss_indices[skip..].iter().zip(&new_embeddings[skip..]) {
-                guard.insert(
-                    keys[orig_idx],
-                    CacheEntry {
-                        embedding: emb.clone(),
-                        last_accessed: now,
-                    },
-                );
+                guard.push(keys[orig_idx], emb.clone());
             }
         }
 
-        // Move originals into results (zero-copy for all, including cached ones).
+        // Move originals into results (zero-copy).
         for (orig_idx, emb) in miss_indices.iter().copied().zip(new_embeddings) {
             results[orig_idx] = Some(emb);
         }

tests/batch_last_run_status_tests.rs

@@ -0,0 +1,191 @@
+//! Tests for batch_get_last_run_status (#1469 N+1 fix).
+//!
+//! Verifies:
+//! 1. Empty input returns empty map
+//! 2. Returns the most recent run status per routine
+//! 3. Routines with no runs are omitted from result
+//! 4. Multiple routines with different statuses are correctly returned
+
+#[cfg(feature = "libsql")]
+mod tests {
+    use std::sync::Arc;
+
+    use chrono::{Duration, Utc};
+    use uuid::Uuid;
+
+    use ironclaw::agent::routine::{
+        Routine, RoutineAction, RoutineGuardrails, RoutineRun, RunStatus, Trigger,
+    };
+    use ironclaw::db::Database;
+
+    async fn create_test_db() -> (Arc<dyn Database>, tempfile::TempDir) {
+        use ironclaw::db::libsql::LibSqlBackend;
+
+        let temp_dir = tempfile::tempdir().expect("tempdir");
+        let db_path = temp_dir.path().join("test.db");
+        let backend = LibSqlBackend::new_local(&db_path)
+            .await
+            .expect("LibSqlBackend");
+        backend.run_migrations().await.expect("migrations");
+        let db: Arc<dyn Database> = Arc::new(backend);
+        (db, temp_dir)
+    }
+
+    fn make_routine(id: Uuid) -> Routine {
+        Routine {
+            id,
+            name: format!("test-routine-{}", id),
+            description: "Test routine".to_string(),
+            user_id: "default".to_string(),
+            enabled: true,
+            trigger: Trigger::Manual,
+            action: RoutineAction::FullJob {
+                title: "Test job".to_string(),
+                description: "Test description".to_string(),
+                max_iterations: 5,
+            },
+            guardrails: RoutineGuardrails {
+                cooldown: std::time::Duration::from_secs(0),
+                max_concurrent: 1,
+                dedup_window: None,
+            },
+            notify: Default::default(),
+            last_run_at: None,
+            next_fire_at: None,
+            run_count: 0,
+            consecutive_failures: 0,
+            state: serde_json::json!({}),
+            created_at: Utc::now(),
+            updated_at: Utc::now(),
+        }
+    }
+
+    fn make_run(
+        routine_id: Uuid,
+        status: RunStatus,
+        started_at: chrono::DateTime<chrono::Utc>,
+    ) -> RoutineRun {
+        RoutineRun {
+            id: Uuid::new_v4(),
+            routine_id,
+            trigger_type: "manual".to_string(),
+            trigger_detail: None,
+            started_at,
+            completed_at: if status == RunStatus::Running {
+                None
+            } else {
+                Some(Utc::now())
+            },
+            status,
+            result_summary: None,
+            tokens_used: None,
+            job_id: None,
+            created_at: Utc::now(),
+        }
+    }
+
+    #[tokio::test]
+    async fn test_batch_get_last_run_status_empty_input() {
+        let (db, _tmp) = create_test_db().await;
+        let result = db
+            .batch_get_last_run_status(&[])
+            .await
+            .expect("batch query");
+        assert!(result.is_empty());
+    }
+
+    #[tokio::test]
+    async fn test_batch_get_last_run_status_returns_latest() {
+        let (db, _tmp) = create_test_db().await;
+
+        let routine_id = Uuid::new_v4();
+        db.create_routine(&make_routine(routine_id))
+            .await
+            .expect("create routine");
+
+        // Create an older run with Ok status
+        let older_run = make_run(routine_id, RunStatus::Ok, Utc::now() - Duration::hours(2));
+        db.create_routine_run(&older_run)
+            .await
+            .expect("create older run");
+        db.complete_routine_run(older_run.id, RunStatus::Ok, None, None)
+            .await
+            .expect("complete older run");
+
+        // Create a newer run with Attention status
+        let newer_run = make_run(
+            routine_id,
+            RunStatus::Attention,
+            Utc::now() - Duration::hours(1),
+        );
+        db.create_routine_run(&newer_run)
+            .await
+            .expect("create newer run");
+        db.complete_routine_run(newer_run.id, RunStatus::Attention, None, None)
+            .await
+            .expect("complete newer run");
+
+        let result = db
+            .batch_get_last_run_status(&[routine_id])
+            .await
+            .expect("batch query");
+        assert_eq!(result.get(&routine_id), Some(&RunStatus::Attention));
+    }
+
+    #[tokio::test]
+    async fn test_batch_get_last_run_status_omits_routines_without_runs() {
+        let (db, _tmp) = create_test_db().await;
+
+        let with_runs = Uuid::new_v4();
+        let without_runs = Uuid::new_v4();
+        db.create_routine(&make_routine(with_runs))
+            .await
+            .expect("create routine");
+        db.create_routine(&make_routine(without_runs))
+            .await
+            .expect("create routine");
+
+        let run = make_run(with_runs, RunStatus::Ok, Utc::now());
+        db.create_routine_run(&run).await.expect("create run");
+        db.complete_routine_run(run.id, RunStatus::Ok, None, None)
+            .await
+            .expect("complete run");
+
+        let result = db
+            .batch_get_last_run_status(&[with_runs, without_runs])
+            .await
+            .expect("batch query");
+        assert_eq!(result.get(&with_runs), Some(&RunStatus::Ok));
+        assert_eq!(result.get(&without_runs), None);
+    }
+
+    #[tokio::test]
+    async fn test_batch_get_last_run_status_multiple_routines() {
+        let (db, _tmp) = create_test_db().await;
+
+        let r1 = Uuid::new_v4();
+        let r2 = Uuid::new_v4();
+        db.create_routine(&make_routine(r1))
+            .await
+            .expect("create r1");
+        db.create_routine(&make_routine(r2))
+            .await
+            .expect("create r2");
+
+        let run1 = make_run(r1, RunStatus::Running, Utc::now());
+        db.create_routine_run(&run1).await.expect("create run1");
+
+        let run2 = make_run(r2, RunStatus::Failed, Utc::now());
+        db.create_routine_run(&run2).await.expect("create run2");
+        db.complete_routine_run(run2.id, RunStatus::Failed, None, None)
+            .await
+            .expect("complete run2");
+
+        let result = db
+            .batch_get_last_run_status(&[r1, r2])
+            .await
+            .expect("batch query");
+        assert_eq!(result.get(&r1), Some(&RunStatus::Running));
+        assert_eq!(result.get(&r2), Some(&RunStatus::Failed));
+    }
+}

tests/e2e/CLAUDE.md

@@ -53,6 +53,7 @@ HEADED=1 pytest scenarios/
 | `test_skills.py` | Skills tab UI visibility, ClawHub search (skipped if registry unreachable), install + remove lifecycle |
 | `test_sse_reconnect.py` | SSE reconnects after programmatic `eventSource.close()` + `connectSSE()`; history is reloaded after reconnect |
 | `test_tool_approval.py` | Approval card appears, buttons disable on approve/deny, parameters toggle via `page.evaluate("showApproval(...)")`; the waiting-approval regression uses a real HTTP tool call |
+| `test_oauth_refresh.py` | Hosted Gmail OAuth regression: complete setup via `/oauth/callback`, expire the stored access token in libSQL, trigger a real `gmail` tool call through `/api/chat/send`, and verify refresh goes through the mock `/oauth/refresh` proxy without forwarding `client_secret` |
 
 ## `helpers.py`
 
@@ -75,6 +76,7 @@ All fixtures are defined in `tests/e2e/conftest.py`. Running `pytest scenarios/`
 | `ironclaw_binary` | Checks `target/debug/ironclaw`; if absent, runs `cargo build --no-default-features --features libsql` (timeout 600s). |
 | `mock_llm_server` | Starts `mock_llm.py --port 0`, reads the assigned port from stdout, waits for `/v1/models` to return 200. Yields the base URL. |
 | `ironclaw_server` | Starts the ironclaw binary with a minimal env (see below), waits for `/api/health` (timeout 60s). Yields the base URL. On teardown sends **SIGINT** (not SIGTERM) so the tokio ctrl_c handler triggers a graceful shutdown and LLVM coverage data is flushed. |
+| `hosted_oauth_refresh_server` | Starts a second ironclaw instance with a dedicated libSQL DB and `GOOGLE_OAUTH_CLIENT_ID=hosted-google-client-id`, while still pointing `IRONCLAW_OAUTH_EXCHANGE_URL` at `mock_llm.py`. Yields a dict with `base_url`, `db_path`, `gateway_user_id`, and `mock_llm_url` for the hosted refresh regression scenario. |
 | `browser` | Launches a single Chromium instance (headless by default; set `HEADED=1` for headed). Shared across all tests. |
 
 ### Function-scoped fixtures
@@ -100,6 +102,8 @@ EMBEDDING_ENABLED=false, SKILLS_ENABLED=true
 ONBOARD_COMPLETED=true   # prevents setup wizard
 ```
 
+The `hosted_oauth_refresh_server` fixture uses the same baseline, but with its own DB/home tempdirs and `GOOGLE_OAUTH_CLIENT_ID=hosted-google-client-id` so hosted OAuth flows exercise proxy credential injection instead of the baked-in desktop Google app.
+
 The binary is also started with `--no-onboard`. Coverage env vars (`CARGO_LLVM_COV*`, `LLVM_*`, `CARGO_ENCODED_RUSTFLAGS`, `CARGO_INCREMENTAL`) are forwarded from the outer environment when present.
 
 ## Mock LLM (`mock_llm.py`)
@@ -113,6 +117,11 @@ python mock_llm.py --port 0
 
 It serves `POST /v1/chat/completions` (streaming + non-streaming) and `GET /v1/models`. Responses are pattern-matched from `CANNED_RESPONSES` against the last user message. Unmatched messages return `"I understand your request."`. The model name reported is always `"mock-model"`.
 
+It also hosts OAuth test endpoints:
+- `POST /oauth/exchange` for hosted auth-code exchange
+- `POST /oauth/refresh` for hosted refresh-token exchange
+- `GET /__mock/oauth/state` and `POST /__mock/oauth/reset` so HTTP E2E scenarios can assert exact proxy payloads and reset counters between setup and refresh assertions
+
 To add a new canned response:
 ```python
 # In mock_llm.py

tests/e2e/conftest.py

@@ -112,6 +112,39 @@ def _reserve_loopback_sockets(count: int) -> list[socket.socket]:
             sock.close()
         raise
 
+async def _stop_process(
+    proc: asyncio.subprocess.Process, *, sig: int | None = None, timeout: float
+) -> None:
+    """Signal a subprocess and wait briefly without masking exit races."""
+    if proc.returncode is not None:
+        return
+
+    try:
+        if sig is None:
+            proc.kill()
+        else:
+            proc.send_signal(sig)
+    except ProcessLookupError:
+        try:
+            await asyncio.wait_for(proc.wait(), timeout=timeout)
+        except asyncio.TimeoutError:
+            pass
+        return
+
+    try:
+        await asyncio.wait_for(proc.wait(), timeout=timeout)
+    except asyncio.TimeoutError:
+        pass
+
+
+def _forward_coverage_env(env: dict[str, str]) -> None:
+    """Forward cargo-llvm-cov env vars into child processes when present."""
+    cov_env_prefixes = ("CARGO_LLVM_COV", "LLVM_")
+    cov_env_extras = ("CARGO_ENCODED_RUSTFLAGS", "CARGO_INCREMENTAL")
+    for key, val in os.environ.items():
+        if key.startswith(cov_env_prefixes) or key in cov_env_extras:
+            env[key] = val
+
 
 @pytest.fixture(scope="session")
 def ironclaw_binary():
@@ -264,14 +297,7 @@ async def ironclaw_server(
         "IRONCLAW_OAUTH_CALLBACK_URL": "https://oauth.test.example/oauth/callback",
         "IRONCLAW_OAUTH_EXCHANGE_URL": mock_llm_server,
     }
-    # Forward LLVM coverage instrumentation env vars when present
-    # (allows cargo-llvm-cov to collect profraw data from E2E runs).
-    # Use prefix matching to stay resilient to cargo-llvm-cov changes.
-    COV_ENV_PREFIXES = ("CARGO_LLVM_COV", "LLVM_")
-    COV_ENV_EXTRAS = ("CARGO_ENCODED_RUSTFLAGS", "CARGO_INCREMENTAL")
-    for key, val in os.environ.items():
-        if key.startswith(COV_ENV_PREFIXES) or key in COV_ENV_EXTRAS:
-            env[key] = val
+    _forward_coverage_env(env)
     proc = await asyncio.create_subprocess_exec(
         ironclaw_binary, "--no-onboard",
         stdin=asyncio.subprocess.DEVNULL,
@@ -279,35 +305,145 @@ async def ironclaw_server(
         stderr=asyncio.subprocess.PIPE,
         env=env,
     )
+    startup_kill_attempted = False
     base_url = f"http://127.0.0.1:{gateway_port}"
     try:
         await wait_for_ready(f"{base_url}/api/health", timeout=60)
         yield base_url
     except TimeoutError:
         # Dump stderr so CI logs show why the server failed to start
+        if proc.returncode is None:
+            startup_kill_attempted = True
+            await _stop_process(proc, timeout=2)
         returncode = proc.returncode
         stderr_bytes = b""
         if proc.stderr:
             try:
                 stderr_bytes = await asyncio.wait_for(proc.stderr.read(8192), timeout=2)
-            except (asyncio.TimeoutError, Exception):
+            except asyncio.TimeoutError:
                 pass
         stderr_text = stderr_bytes.decode("utf-8", errors="replace")
-        proc.kill()
         pytest.fail(
             f"ironclaw server failed to start on port {gateway_port} "
             f"(returncode={returncode}).\nstderr:\n{stderr_text}"
         )
     finally:
         if proc.returncode is None:
-            # Use SIGINT (not SIGTERM) so tokio's ctrl_c handler triggers a
-            # graceful shutdown.  This lets the LLVM coverage runtime run its
-            # atexit handler and flush .profraw files for cargo-llvm-cov.
-            proc.send_signal(signal.SIGINT)
-            try:
-                await asyncio.wait_for(proc.wait(), timeout=10)
-            except asyncio.TimeoutError:
-                proc.kill()
+            if startup_kill_attempted:
+                await _stop_process(proc, timeout=2)
+            else:
+                # Use SIGINT (not SIGTERM) so tokio's ctrl_c handler triggers a
+                # graceful shutdown.  This lets the LLVM coverage runtime run its
+                # atexit handler and flush .profraw files for cargo-llvm-cov.
+                await _stop_process(proc, sig=signal.SIGINT, timeout=10)
+                if proc.returncode is None:
+                    await _stop_process(proc, timeout=2)
+
+
+@pytest.fixture(scope="session")
+async def hosted_oauth_refresh_server(
+    ironclaw_binary,
+    mock_llm_server,
+    wasm_tools_dir,
+):
+    """Start a hosted-mode ironclaw instance for OAuth refresh regression tests."""
+    reserved = _reserve_loopback_sockets(2)
+    db_tmpdir = tempfile.TemporaryDirectory(prefix="ironclaw-e2e-hosted-oauth-db-")
+    home_tmpdir = tempfile.TemporaryDirectory(prefix="ironclaw-e2e-hosted-oauth-home-")
+
+    try:
+        gateway_port = reserved[0].getsockname()[1]
+        http_port = reserved[1].getsockname()[1]
+        for sock in reserved:
+            if sock.fileno() != -1:
+                sock.close()
+
+        db_path = os.path.join(db_tmpdir.name, "hosted-oauth-refresh.db")
+        home_dir = home_tmpdir.name
+        env = {
+            "PATH": os.environ.get("PATH", "/usr/bin:/bin"),
+            "HOME": home_dir,
+            "IRONCLAW_BASE_DIR": os.path.join(home_dir, ".ironclaw"),
+            "RUST_LOG": "ironclaw=info",
+            "RUST_BACKTRACE": "1",
+            "IRONCLAW_OWNER_ID": OWNER_SCOPE_ID,
+            "GATEWAY_ENABLED": "true",
+            "GATEWAY_HOST": "127.0.0.1",
+            "GATEWAY_PORT": str(gateway_port),
+            "GATEWAY_AUTH_TOKEN": AUTH_TOKEN,
+            "GATEWAY_USER_ID": OWNER_SCOPE_ID,
+            "HTTP_HOST": "127.0.0.1",
+            "HTTP_PORT": str(http_port),
+            "HTTP_WEBHOOK_SECRET": HTTP_WEBHOOK_SECRET,
+            "CLI_ENABLED": "false",
+            "LLM_BACKEND": "openai_compatible",
+            "LLM_BASE_URL": mock_llm_server,
+            "LLM_MODEL": "mock-model",
+            "DATABASE_BACKEND": "libsql",
+            "LIBSQL_PATH": db_path,
+            "SECRETS_MASTER_KEY": "0123456789abcdef0123456789abcdef0123456789abcdef0123456789abcdef",
+            "SANDBOX_ENABLED": "false",
+            "SKILLS_ENABLED": "true",
+            "ROUTINES_ENABLED": "true",
+            "HEARTBEAT_ENABLED": "false",
+            "EMBEDDING_ENABLED": "false",
+            "WASM_ENABLED": "true",
+            "WASM_TOOLS_DIR": wasm_tools_dir,
+            "WASM_CHANNELS_DIR": _WASM_CHANNELS_TMPDIR.name,
+            "ONBOARD_COMPLETED": "true",
+            "IRONCLAW_OAUTH_CALLBACK_URL": "https://oauth.test.example/oauth/callback",
+            "IRONCLAW_OAUTH_EXCHANGE_URL": mock_llm_server,
+            "GOOGLE_OAUTH_CLIENT_ID": "hosted-google-client-id",
+        }
+        _forward_coverage_env(env)
+
+        proc = await asyncio.create_subprocess_exec(
+            ironclaw_binary, "--no-onboard",
+            stdin=asyncio.subprocess.DEVNULL,
+            stdout=asyncio.subprocess.PIPE,
+            stderr=asyncio.subprocess.PIPE,
+            env=env,
+        )
+        startup_kill_attempted = False
+        base_url = f"http://127.0.0.1:{gateway_port}"
+        try:
+            await wait_for_ready(f"{base_url}/api/health", timeout=60)
+            yield {
+                "base_url": base_url,
+                "db_path": db_path,
+                "gateway_user_id": OWNER_SCOPE_ID,
+                "mock_llm_url": mock_llm_server,
+            }
+        except TimeoutError:
+            if proc.returncode is None:
+                startup_kill_attempted = True
+                await _stop_process(proc, timeout=2)
+            returncode = proc.returncode
+            stderr_bytes = b""
+            if proc.stderr:
+                try:
+                    stderr_bytes = await asyncio.wait_for(proc.stderr.read(8192), timeout=2)
+                except asyncio.TimeoutError:
+                    pass
+            stderr_text = stderr_bytes.decode("utf-8", errors="replace")
+            pytest.fail(
+                f"hosted oauth refresh server failed to start on port {gateway_port} "
+                f"(returncode={returncode}).\nstderr:\n{stderr_text}"
+            )
+        finally:
+            if proc.returncode is None:
+                if startup_kill_attempted:
+                    await _stop_process(proc, timeout=2)
+                else:
+                    await _stop_process(proc, sig=signal.SIGINT, timeout=10)
+                    if proc.returncode is None:
+                        await _stop_process(proc, timeout=2)
+    finally:
+        for sock in reserved:
+            if sock.fileno() != -1:
+                sock.close()
+        db_tmpdir.cleanup()
+        home_tmpdir.cleanup()
 
 
 @pytest.fixture(scope="session")
@@ -362,12 +498,7 @@ async def http_channel_server_without_secret(
         "IRONCLAW_OAUTH_CALLBACK_URL": "https://oauth.test.example/oauth/callback",
         "IRONCLAW_OAUTH_EXCHANGE_URL": mock_llm_server,
     }
-    # Forward LLVM coverage instrumentation env vars when present
-    COV_ENV_PREFIXES = ("CARGO_LLVM_COV", "LLVM_")
-    COV_ENV_EXTRAS = ("CARGO_ENCODED_RUSTFLAGS", "CARGO_INCREMENTAL")
-    for key, val in os.environ.items():
-        if key.startswith(COV_ENV_PREFIXES) or key in COV_ENV_EXTRAS:
-            env[key] = val
+    _forward_coverage_env(env)
     proc = await asyncio.create_subprocess_exec(
         ironclaw_binary, "--no-onboard",
         stdin=asyncio.subprocess.DEVNULL,
@@ -375,6 +506,7 @@ async def http_channel_server_without_secret(
         stderr=asyncio.subprocess.PIPE,
         env=env,
     )
+    startup_kill_attempted = False
     gateway_url = f"http://127.0.0.1:{gateway_port}"
     http_base_url = f"http://127.0.0.1:{http_port}"
     try:
@@ -383,15 +515,17 @@ async def http_channel_server_without_secret(
         yield http_base_url
     except TimeoutError:
         # Dump stderr so CI logs show why the server failed to start
+        if proc.returncode is None:
+            startup_kill_attempted = True
+            await _stop_process(proc, timeout=2)
         returncode = proc.returncode
         stderr_bytes = b""
         if proc.stderr:
             try:
                 stderr_bytes = await asyncio.wait_for(proc.stderr.read(8192), timeout=2)
-            except (asyncio.TimeoutError, Exception):
+            except asyncio.TimeoutError:
                 pass
         stderr_text = stderr_bytes.decode("utf-8", errors="replace")
-        proc.kill()
         pytest.fail(
             f"ironclaw server without webhook secret failed to start on ports "
             f"gateway={gateway_port}, http={http_port} "
@@ -399,14 +533,15 @@ async def http_channel_server_without_secret(
         )
     finally:
         if proc.returncode is None:
-            # Use SIGINT (not SIGTERM) so tokio's ctrl_c handler triggers a
-            # graceful shutdown.  This lets the LLVM coverage runtime run its
-            # atexit handler and flush .profraw files for cargo-llvm-cov.
-            proc.send_signal(signal.SIGINT)
-            try:
-                await asyncio.wait_for(proc.wait(), timeout=10)
-            except asyncio.TimeoutError:
-                proc.kill()
+            if startup_kill_attempted:
+                await _stop_process(proc, timeout=2)
+            else:
+                # Use SIGINT (not SIGTERM) so tokio's ctrl_c handler triggers a
+                # graceful shutdown.  This lets the LLVM coverage runtime run its
+                # atexit handler and flush .profraw files for cargo-llvm-cov.
+                await _stop_process(proc, sig=signal.SIGINT, timeout=10)
+                if proc.returncode is None:
+                    await _stop_process(proc, timeout=2)
 
 
 @pytest.fixture(scope="session")

tests/e2e/mock_llm.py

@@ -34,6 +34,15 @@ TOOL_CALL_PATTERNS = [
             "body": {"label": m.group("label")},
         },
     ),
+    (
+        re.compile(r"check gmail unread|gmail unread", re.IGNORECASE),
+        "gmail",
+        lambda _: {
+            "action": "list_messages",
+            "query": "is:unread",
+            "max_results": 1,
+        },
+    ),
     (re.compile(r"what time|current time", re.IGNORECASE), "time", lambda _: {"operation": "now"}),
     (
         re.compile(
@@ -91,6 +100,15 @@ TOOL_CALL_PATTERNS = [
 ]
 
 
+def _new_oauth_state() -> dict:
+    return {
+        "exchange_count": 0,
+        "refresh_count": 0,
+        "last_exchange": None,
+        "last_refresh": None,
+    }
+
+
 def _last_user_content(messages: list[dict]) -> str:
     for msg in reversed(messages):
         if msg.get("role") == "user":
@@ -272,6 +290,12 @@ async def oauth_exchange(request: web.Request) -> web.Response:
     specific token params such as RFC 8707 `resource` are forwarded here.
     """
     data = await request.post()
+    oauth_state = request.app["oauth_state"]
+    oauth_state["exchange_count"] += 1
+    oauth_state["last_exchange"] = {
+        "authorization": request.headers.get("Authorization"),
+        "form": dict(data),
+    }
     code = data.get("code", "")
     access_token_field = data.get("access_token_field", "access_token")
 
@@ -290,6 +314,39 @@ async def oauth_exchange(request: web.Request) -> web.Response:
     })
 
 
+async def oauth_refresh(request: web.Request) -> web.Response:
+    """Mock OAuth token refresh proxy for hosted refresh E2E tests."""
+    data = await request.post()
+    oauth_state = request.app["oauth_state"]
+    oauth_state["refresh_count"] += 1
+    oauth_state["last_refresh"] = {
+        "authorization": request.headers.get("Authorization"),
+        "form": dict(data),
+    }
+
+    if request.headers.get("Authorization") != "Bearer e2e-test-token":
+        return web.json_response({"error": "invalid_gateway_auth"}, status=401)
+    if data.get("client_id") != "hosted-google-client-id":
+        return web.json_response({"error": "invalid_client_id"}, status=400)
+    if "client_secret" in data:
+        return web.json_response({"error": "unexpected_client_secret"}, status=400)
+
+    return web.json_response({
+        "access_token": "mock-refreshed-access-token",
+        "refresh_token": "mock-rotated-refresh-token",
+        "expires_in": 3600,
+    })
+
+
+async def oauth_state_handler(request: web.Request) -> web.Response:
+    return web.json_response(request.app["oauth_state"])
+
+
+async def oauth_reset(request: web.Request) -> web.Response:
+    request.app["oauth_state"] = _new_oauth_state()
+    return web.json_response({"ok": True})
+
+
 async def models(_request: web.Request) -> web.Response:
     return web.json_response({
         "object": "list",
@@ -424,12 +481,16 @@ def main():
     parser.add_argument("--port", type=int, default=0)
     args = parser.parse_args()
     app = web.Application()
+    app["oauth_state"] = _new_oauth_state()
     # Register both /v1/ and non-/v1/ paths (rig-core omits the /v1/ prefix)
     app.router.add_post("/v1/chat/completions", chat_completions)
     app.router.add_post("/chat/completions", chat_completions)
     app.router.add_get("/v1/models", models)
     app.router.add_get("/models", models)
     app.router.add_post("/oauth/exchange", oauth_exchange)
+    app.router.add_post("/oauth/refresh", oauth_refresh)
+    app.router.add_get("/__mock/oauth/state", oauth_state_handler)
+    app.router.add_post("/__mock/oauth/reset", oauth_reset)
     # Mock MCP server endpoints
     app.router.add_post("/mcp", mcp_endpoint)
     app.router.add_post("/mcp-400", mcp_endpoint_400)

tests/e2e/scenarios/test_oauth_refresh.py

@@ -0,0 +1,227 @@
+"""Hosted OAuth refresh HTTP regression test.
+
+Runs a real ironclaw binary in hosted mode, expires a stored Gmail access
+token in the libSQL database, triggers a real gmail tool call through the
+chat API, and verifies that refresh uses the hosted proxy endpoint.
+"""
+
+import asyncio
+import sqlite3
+from datetime import datetime, timezone
+from urllib.parse import parse_qs, urlparse
+
+import httpx
+
+from helpers import api_get, api_post
+
+
+def _extract_state(auth_url: str) -> str:
+    parsed = urlparse(auth_url)
+    state = parse_qs(parsed.query).get("state", [None])[0]
+    assert state, f"auth_url should include state: {auth_url}"
+    return state
+
+
+def _parse_timestamp(value: str | None) -> datetime | None:
+    if value is None:
+        return None
+    return datetime.fromisoformat(value.replace("Z", "+00:00"))
+
+
+def _expire_access_token(db_path: str, user_id: str, secret_name: str) -> None:
+    with sqlite3.connect(db_path) as conn:
+        cursor = conn.execute(
+            """
+            UPDATE secrets
+            SET expires_at = strftime('%Y-%m-%dT%H:%M:%fZ', 'now', '-1 hour')
+            WHERE user_id = ?1 AND name = ?2
+            """,
+            (user_id, secret_name),
+        )
+        conn.commit()
+    assert cursor.rowcount == 1, f"Expected one secret row for {user_id}/{secret_name}"
+
+
+def _find_secret_row(
+    db_path: str,
+    secret_name: str,
+) -> tuple[str, str | None, str | None]:
+    with sqlite3.connect(db_path) as conn:
+        row = conn.execute(
+            """
+            SELECT user_id, expires_at, updated_at
+            FROM secrets
+            WHERE name = ?1
+            ORDER BY updated_at DESC
+            LIMIT 1
+            """,
+            (secret_name,),
+        ).fetchone()
+    assert row is not None, f"Missing secret row for {secret_name}"
+    return row[0], row[1], row[2]
+
+
+async def _get_extension(base_url: str, name: str) -> dict | None:
+    response = await api_get(base_url, "/api/extensions", timeout=15)
+    response.raise_for_status()
+    for extension in response.json().get("extensions", []):
+        if extension["name"] == name:
+            return extension
+    return None
+
+
+async def _reset_mock_oauth_state(mock_base_url: str) -> None:
+    async with httpx.AsyncClient() as client:
+        response = await client.post(f"{mock_base_url}/__mock/oauth/reset", timeout=10)
+    response.raise_for_status()
+
+
+async def _get_mock_oauth_state(mock_base_url: str) -> dict:
+    async with httpx.AsyncClient() as client:
+        response = await client.get(f"{mock_base_url}/__mock/oauth/state", timeout=10)
+    response.raise_for_status()
+    return response.json()
+
+
+async def _approve_pending_request(base_url: str, thread_id: str, request_id: str) -> None:
+    response = await api_post(
+        base_url,
+        "/api/chat/approval",
+        json={"request_id": request_id, "action": "approve", "thread_id": thread_id},
+        timeout=15,
+    )
+    assert response.status_code == 202, (
+        f"Approval submission failed: {response.status_code} {response.text[:400]}"
+    )
+
+
+async def _wait_for_gmail_tool_call(base_url: str, thread_id: str, timeout: float = 30.0) -> dict:
+    approved_request_ids = set()
+    for _ in range(int(timeout * 2)):
+        response = await api_get(
+            base_url,
+            f"/api/chat/history?thread_id={thread_id}",
+            timeout=15,
+        )
+        response.raise_for_status()
+        history = response.json()
+
+        pending = history.get("pending_approval")
+        if pending and pending["request_id"] not in approved_request_ids:
+            await _approve_pending_request(base_url, thread_id, pending["request_id"])
+            approved_request_ids.add(pending["request_id"])
+
+        for turn in history.get("turns", []):
+            for tool_call in turn.get("tool_calls", []):
+                if tool_call.get("name") == "gmail":
+                    return history
+
+        await asyncio.sleep(0.5)
+
+    raise AssertionError(f"Timed out waiting for gmail tool call in thread {thread_id}")
+
+
+async def _wait_for_refresh_request(mock_base_url: str, timeout: float = 20.0) -> dict:
+    for _ in range(int(timeout * 2)):
+        state = await _get_mock_oauth_state(mock_base_url)
+        if state.get("refresh_count") == 1:
+            return state
+        await asyncio.sleep(0.5)
+    raise AssertionError("Timed out waiting for exactly one OAuth refresh request")
+
+
+async def test_hosted_gmail_oauth_refresh_uses_proxy(hosted_oauth_refresh_server):
+    server = hosted_oauth_refresh_server["base_url"]
+    db_path = hosted_oauth_refresh_server["db_path"]
+    mock_base_url = hosted_oauth_refresh_server["mock_llm_url"]
+
+    install_response = await api_post(
+        server,
+        "/api/extensions/install",
+        json={"name": "gmail"},
+        timeout=180,
+    )
+    assert install_response.status_code == 200, install_response.text
+    assert install_response.json().get("success") is True
+
+    setup_response = await api_post(
+        server,
+        "/api/extensions/gmail/setup",
+        json={"secrets": {}},
+        timeout=30,
+    )
+    assert setup_response.status_code == 200, setup_response.text
+    setup_data = setup_response.json()
+    assert setup_data.get("success") is True, setup_data
+    auth_url = setup_data.get("auth_url")
+    assert auth_url, setup_data
+    auth_params = parse_qs(urlparse(auth_url).query)
+    assert auth_params.get("client_id") == ["hosted-google-client-id"]
+
+    async with httpx.AsyncClient() as client:
+        callback_response = await client.get(
+            f"{server}/oauth/callback",
+            params={"code": "mock_auth_code", "state": _extract_state(auth_url)},
+            timeout=30,
+            follow_redirects=True,
+        )
+
+    assert callback_response.status_code == 200, callback_response.text[:400]
+    callback_body = callback_response.text.lower()
+    assert "connected" in callback_body or "success" in callback_body
+
+    gmail = await _get_extension(server, "gmail")
+    assert gmail is not None, "gmail should be installed"
+    assert gmail["authenticated"] is True, gmail
+    assert "gmail" in gmail.get("tools", []), gmail
+
+    await _reset_mock_oauth_state(mock_base_url)
+
+    stored_user_id, expires_before, updated_before = _find_secret_row(
+        db_path, "google_oauth_token"
+    )
+    assert _parse_timestamp(expires_before) is not None
+    assert _parse_timestamp(updated_before) is not None
+
+    await asyncio.sleep(0.1)
+    _expire_access_token(db_path, stored_user_id, "google_oauth_token")
+
+    thread_response = await api_post(server, "/api/chat/thread/new", timeout=15)
+    assert thread_response.status_code == 200, thread_response.text
+    thread_id = thread_response.json()["id"]
+
+    send_response = await api_post(
+        server,
+        "/api/chat/send",
+        json={"content": "check gmail unread", "thread_id": thread_id},
+        timeout=30,
+    )
+    assert send_response.status_code == 202, send_response.text
+
+    history = await _wait_for_gmail_tool_call(server, thread_id)
+    assert any(
+        tool_call.get("name") == "gmail"
+        for turn in history.get("turns", [])
+        for tool_call in turn.get("tool_calls", [])
+    ), history
+
+    oauth_state = await _wait_for_refresh_request(mock_base_url)
+    assert oauth_state["refresh_count"] == 1, oauth_state
+    last_refresh = oauth_state["last_refresh"]
+    assert last_refresh is not None, oauth_state
+    assert last_refresh["authorization"] == "Bearer e2e-test-token"
+    assert last_refresh["form"]["client_id"] == "hosted-google-client-id"
+    assert "client_secret" not in last_refresh["form"], last_refresh
+
+    refreshed_user_id, expires_after, updated_after = _find_secret_row(
+        db_path, "google_oauth_token"
+    )
+    assert refreshed_user_id == stored_user_id
+    expires_after_dt = _parse_timestamp(expires_after)
+    updated_after_dt = _parse_timestamp(updated_after)
+    updated_before_dt = _parse_timestamp(updated_before)
+    assert expires_after_dt is not None
+    assert updated_after_dt is not None
+    assert updated_before_dt is not None
+    assert expires_after_dt > datetime.now(timezone.utc)
+    assert updated_after_dt > updated_before_dt

tests/e2e_advanced_traces.rs

@@ -661,7 +661,7 @@ mod advanced {
             .await
             .expect("failed to inject test token");
 
-        let activate_result = ext_mgr.activate("mock-notion").await;
+        let activate_result = ext_mgr.activate("mock-notion", "default").await;
         assert!(
             activate_result.is_ok(),
             "activation failed: {:?}",

tests/e2e_routine_heartbeat.rs

@@ -561,11 +561,7 @@ mod tests {
             "deploy to production now",
         );
         let fired = engine
-            .check_event_triggers(
-                &matching_msg.user_id,
-                &matching_msg.channel,
-                &matching_msg.content,
-            )
+            .check_event_triggers(&matching_msg, &matching_msg.content)
             .await;
         assert!(
             fired >= 1,
@@ -584,11 +580,7 @@ mod tests {
             "check the staging environment",
         );
         let fired_neg = engine
-            .check_event_triggers(
-                &non_matching_msg.user_id,
-                &non_matching_msg.channel,
-                &non_matching_msg.content,
-            )
+            .check_event_triggers(&non_matching_msg, &non_matching_msg.content)
             .await;
         assert_eq!(fired_neg, 0, "Expected 0 routines fired on non-match");
     }
@@ -652,7 +644,7 @@ mod tests {
             "deploy to production now",
         );
         let guest_fired = engine
-            .check_event_triggers(&guest_msg.user_id, &guest_msg.channel, &guest_msg.content)
+            .check_event_triggers(&guest_msg, &guest_msg.content)
             .await;
         assert_eq!(
             guest_fired, 0,
@@ -677,7 +669,7 @@ mod tests {
             "deploy to production now",
         );
         let owner_fired = engine
-            .check_event_triggers(&owner_msg.user_id, &owner_msg.channel, &owner_msg.content)
+            .check_event_triggers(&owner_msg, &owner_msg.content)
             .await;
         assert!(
             owner_fired >= 1,
@@ -906,9 +898,7 @@ mod tests {
             "default",
             "test-cooldown trigger",
         );
-        let fired1 = engine
-            .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-            .await;
+        let fired1 = engine.check_event_triggers(&msg, &msg.content).await;
         assert!(fired1 >= 1, "First fire should work");
 
         // Give spawn time, then update last_run_at to simulate recent execution.
@@ -923,9 +913,7 @@ mod tests {
         engine.refresh_event_cache().await;
 
         // Second fire should be blocked by cooldown.
-        let fired2 = engine
-            .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-            .await;
+        let fired2 = engine.check_event_triggers(&msg, &msg.content).await;
         assert_eq!(fired2, 0, "Second fire should be blocked by cooldown");
     }
 
@@ -1095,9 +1083,7 @@ mod tests {
         engine.refresh_event_cache().await;
 
         let msg = IncomingMessage::new("test", "default", "DISABLE_ME");
-        let fired_before = engine
-            .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-            .await;
+        let fired_before = engine.check_event_triggers(&msg, &msg.content).await;
         assert!(fired_before >= 1, "Expected routine to fire before disable");
 
         // Simulate what routines_toggle_handler now does: update DB, then refresh.
@@ -1106,9 +1092,7 @@ mod tests {
         db.update_routine(&routine).await.expect("update_routine");
         engine.refresh_event_cache().await;
 
-        let fired_after = engine
-            .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-            .await;
+        let fired_after = engine.check_event_triggers(&msg, &msg.content).await;
         assert_eq!(
             fired_after, 0,
             "Disabled routine must not fire after cache refresh"
@@ -1134,10 +1118,7 @@ mod tests {
 
         let msg = IncomingMessage::new("test", "default", "DELETE_ME");
         assert!(
-            engine
-                .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-                .await
-                >= 1,
+            engine.check_event_triggers(&msg, &msg.content).await >= 1,
             "Expected routine to fire before delete"
         );
 
@@ -1146,9 +1127,7 @@ mod tests {
         engine.refresh_event_cache().await;
 
         assert_eq!(
-            engine
-                .check_event_triggers(&msg.user_id, &msg.channel, &msg.content)
-                .await,
+            engine.check_event_triggers(&msg, &msg.content).await,
             0,
             "Deleted routine must not fire after cache refresh"
         );
@@ -1462,8 +1441,9 @@ mod tests {
         db.create_routine(&routine).await.expect("create_routine");
         engine.refresh_event_cache().await;
 
+        let trigger_msg = IncomingMessage::new("test", "default", "owner-gate");
         let fired = engine
-            .check_event_triggers("default", "test", "owner-gate")
+            .check_event_triggers(&trigger_msg, &trigger_msg.content)
             .await;
         assert_eq!(fired, 1, "expected one matching event routine");
 

tests/e2e_telegram_message_routing.rs

@@ -200,6 +200,7 @@ mod tests {
             document_extraction: None,
             sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
             builder: None,
+            llm_backend: "nearai".to_string(),
         };
 
         let gateway = Arc::new(TestChannel::new());

tests/module_init_integration.rs

@@ -216,7 +216,7 @@ async fn extension_manager_with_process_manager_constructs() {
     );
 
     // Verify the manager is functional — list returns Ok.
-    let result = manager.list(None, false).await;
+    let result = manager.list(None, false, "test").await;
     assert!(result.is_ok(), "list should succeed on empty manager");
     assert!(result.unwrap().is_empty());
 }

tests/multi_tenant_system_prompt.rs

@@ -0,0 +1,240 @@
+//! Tests proving that multi-tenant system prompts are broken.
+//!
+//! Bug: In multi-tenant mode, the agent loop uses `self.workspace()` which
+//! returns a single shared workspace (user_id="default"). Identity files
+//! (IDENTITY.md, SOUL.md, USER.md) seeded under per-user IDs ("alice",
+//! "bob") are invisible to this workspace, so the system prompt is
+//! empty/wrong.
+//!
+//! These tests:
+//! 1. Seed identity files for two users (alice, bob) in the database
+//! 2. Send messages as each user
+//! 3. Verify the system prompt in captured LLM requests contains the
+//!    correct user's identity
+//! 4. Verify user A's identity doesn't leak into user B's prompt
+//!
+//! All tests are expected to FAIL until the bug is fixed.
+
+#[cfg(feature = "libsql")]
+mod support;
+
+#[cfg(feature = "libsql")]
+mod tests {
+    use std::sync::Arc;
+    use std::time::Duration;
+
+    use ironclaw::channels::IncomingMessage;
+    use ironclaw::llm::Role;
+    use ironclaw::workspace::Workspace;
+
+    use crate::support::test_rig::TestRigBuilder;
+    use crate::support::trace_llm::{LlmTrace, TraceResponse, TraceStep};
+
+    const TIMEOUT: Duration = Duration::from_secs(15);
+
+    const ALICE_USER_ID: &str = "alice";
+    const BOB_USER_ID: &str = "bob";
+
+    const ALICE_IDENTITY: &str = "You are Alice's personal assistant. \
+        Alice is a software engineer who lives in Seattle.";
+    const BOB_IDENTITY: &str = "You are Bob's personal assistant. \
+        Bob is a marine biologist who lives in Miami.";
+
+    /// Create a simple trace that returns a canned text response.
+    /// We need one step per message we plan to send.
+    fn simple_trace(num_steps: usize) -> LlmTrace {
+        let steps: Vec<TraceStep> = (0..num_steps)
+            .map(|i| TraceStep {
+                request_hint: None,
+                response: TraceResponse::Text {
+                    content: format!("Response {}", i),
+                    input_tokens: 100,
+                    output_tokens: 10,
+                },
+                expected_tool_results: Vec::new(),
+            })
+            .collect();
+
+        // Create separate turns for each step so the trace replays correctly.
+        let turns: Vec<crate::support::trace_llm::TraceTurn> = steps
+            .into_iter()
+            .enumerate()
+            .map(|(i, step)| crate::support::trace_llm::TraceTurn {
+                user_input: format!("message {}", i),
+                steps: vec![step],
+                expects: Default::default(),
+            })
+            .collect();
+
+        LlmTrace::new("test-model", turns)
+    }
+
+    /// Seed identity files for a user by creating a workspace scoped to that
+    /// user and writing IDENTITY.md.
+    async fn seed_identity(db: &Arc<dyn ironclaw::db::Database>, user_id: &str, content: &str) {
+        let ws = Workspace::new_with_db(user_id, db.clone());
+        ws.write("IDENTITY.md", content)
+            .await
+            .unwrap_or_else(|e| panic!("Failed to seed IDENTITY.md for {user_id}: {e}"));
+    }
+
+    /// Extract the system prompt from captured LLM requests.
+    ///
+    /// The system prompt is the first message with role=System in the first
+    /// LLM request for a given turn.
+    fn extract_system_prompt(requests: &[Vec<ironclaw::llm::ChatMessage>]) -> Option<String> {
+        requests.last().and_then(|msgs| {
+            msgs.iter()
+                .find(|m| matches!(m.role, Role::System))
+                .map(|m| m.content.clone())
+        })
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 1: Alice's identity should appear in system prompt when messaging
+    // as Alice.
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn alice_system_prompt_contains_alice_identity() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        // Seed alice's identity into the database
+        let db = rig.database();
+        seed_identity(db, ALICE_USER_ID, ALICE_IDENTITY).await;
+
+        // Send a message AS alice (using her user_id)
+        let msg = IncomingMessage::new("test", ALICE_USER_ID, "Hello, who am I?");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        // The system prompt sent to the LLM should contain Alice's identity
+        let requests = rig.captured_llm_requests();
+        let system_prompt =
+            extract_system_prompt(&requests).expect("Expected a system prompt in the LLM request");
+
+        assert!(
+            system_prompt.contains("Alice is a software engineer"),
+            "System prompt should contain Alice's identity when messaging as Alice.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 2: Bob's identity should appear in system prompt when messaging
+    // as Bob.
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn bob_system_prompt_contains_bob_identity() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        // Seed bob's identity into the database
+        let db = rig.database();
+        seed_identity(db, BOB_USER_ID, BOB_IDENTITY).await;
+
+        // Send a message AS bob
+        let msg = IncomingMessage::new("test", BOB_USER_ID, "Hello, who am I?");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        // The system prompt should contain Bob's identity
+        let requests = rig.captured_llm_requests();
+        let system_prompt =
+            extract_system_prompt(&requests).expect("Expected a system prompt in the LLM request");
+
+        assert!(
+            system_prompt.contains("Bob is a marine biologist"),
+            "System prompt should contain Bob's identity when messaging as Bob.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 3: Alice's identity must NOT appear in Bob's system prompt.
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn alice_identity_does_not_leak_into_bob_prompt() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        // Seed BOTH users' identities
+        let db = rig.database();
+        seed_identity(db, ALICE_USER_ID, ALICE_IDENTITY).await;
+        seed_identity(db, BOB_USER_ID, BOB_IDENTITY).await;
+
+        // Send a message AS bob
+        let msg = IncomingMessage::new("test", BOB_USER_ID, "Tell me about myself");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        // Bob's prompt must NOT contain Alice's identity
+        let requests = rig.captured_llm_requests();
+        let system_prompt = extract_system_prompt(&requests);
+
+        if let Some(ref prompt) = system_prompt {
+            assert!(
+                !prompt.contains("Alice is a software engineer"),
+                "Alice's identity LEAKED into Bob's system prompt!\n\
+                 System prompt:\n{prompt}"
+            );
+        }
+        // Also verify Bob's identity IS present (compound check)
+        let prompt = system_prompt.expect("Expected a system prompt in the LLM request");
+        assert!(
+            prompt.contains("Bob is a marine biologist"),
+            "Bob's own identity should be in his system prompt.\n\
+             Actual system prompt:\n{prompt}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 4: Bob's identity must NOT appear in Alice's system prompt.
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn bob_identity_does_not_leak_into_alice_prompt() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        // Seed BOTH users' identities
+        let db = rig.database();
+        seed_identity(db, ALICE_USER_ID, ALICE_IDENTITY).await;
+        seed_identity(db, BOB_USER_ID, BOB_IDENTITY).await;
+
+        // Send a message AS alice
+        let msg = IncomingMessage::new("test", ALICE_USER_ID, "Tell me about myself");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        // Alice's prompt must NOT contain Bob's identity
+        let requests = rig.captured_llm_requests();
+        let system_prompt = extract_system_prompt(&requests);
+
+        if let Some(ref prompt) = system_prompt {
+            assert!(
+                !prompt.contains("Bob is a marine biologist"),
+                "Bob's identity LEAKED into Alice's system prompt!\n\
+                 System prompt:\n{prompt}"
+            );
+        }
+        // Also verify Alice's identity IS present
+        let prompt = system_prompt.expect("Expected a system prompt in the LLM request");
+        assert!(
+            prompt.contains("Alice is a software engineer"),
+            "Alice's own identity should be in her system prompt.\n\
+             Actual system prompt:\n{prompt}"
+        );
+
+        rig.shutdown();
+    }
+}

tests/openai_compat_integration.rs

@@ -191,8 +191,9 @@ async fn start_test_server_with_provider(
 ) -> (SocketAddr, Arc<GatewayState>) {
     let state = Arc::new(GatewayState {
         msg_tx: tokio::sync::RwLock::new(None),
-        sse: SseManager::new(),
+        sse: Arc::new(SseManager::new()),
         workspace: None,
+        workspace_pool: None,
         session_manager: None,
         log_broadcaster: None,
         log_level_handle: None,
@@ -202,13 +203,14 @@ async fn start_test_server_with_provider(
         job_manager: None,
         prompt_queue: None,
         scheduler: None,
-        user_id: "test-user".to_string(),
+        owner_id: "test-user".to_string(),
+        default_sender_id: "test-user".to_string(),
         shutdown_tx: tokio::sync::RwLock::new(None),
         ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
         llm_provider: Some(llm_provider),
         skill_registry: None,
         skill_catalog: None,
-        chat_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(30, 60),
+        chat_rate_limiter: ironclaw::channels::web::server::PerUserRateLimiter::new(30, 60),
         oauth_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         webhook_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         registry_entries: Vec::new(),
@@ -218,8 +220,12 @@ async fn start_test_server_with_provider(
         active_config: ironclaw::channels::web::server::ActiveConfigSnapshot::default(),
     });
 
+    let auth = ironclaw::channels::web::auth::MultiAuthState::single(
+        AUTH_TOKEN.to_string(),
+        "test-user".to_string(),
+    );
     let addr: SocketAddr = "127.0.0.1:0".parse().unwrap();
-    let bound_addr = start_server(addr, state.clone(), AUTH_TOKEN.to_string())
+    let bound_addr = start_server(addr, state.clone(), auth)
         .await
         .expect("Failed to start test server");
 
@@ -684,8 +690,9 @@ async fn test_no_llm_provider_returns_503() {
     // Create state WITHOUT llm_provider
     let state = Arc::new(GatewayState {
         msg_tx: tokio::sync::RwLock::new(None),
-        sse: SseManager::new(),
+        sse: Arc::new(SseManager::new()),
         workspace: None,
+        workspace_pool: None,
         session_manager: None,
         log_broadcaster: None,
         log_level_handle: None,
@@ -695,13 +702,14 @@ async fn test_no_llm_provider_returns_503() {
         job_manager: None,
         prompt_queue: None,
         scheduler: None,
-        user_id: "test-user".to_string(),
+        owner_id: "test-user".to_string(),
+        default_sender_id: "test-user".to_string(),
         shutdown_tx: tokio::sync::RwLock::new(None),
         ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
         llm_provider: None, // No LLM!
         skill_registry: None,
         skill_catalog: None,
-        chat_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(30, 60),
+        chat_rate_limiter: ironclaw::channels::web::server::PerUserRateLimiter::new(30, 60),
         oauth_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         webhook_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         registry_entries: Vec::new(),
@@ -711,10 +719,12 @@ async fn test_no_llm_provider_returns_503() {
         active_config: ironclaw::channels::web::server::ActiveConfigSnapshot::default(),
     });
 
+    let auth = ironclaw::channels::web::auth::MultiAuthState::single(
+        AUTH_TOKEN.to_string(),
+        "test-user".to_string(),
+    );
     let addr: SocketAddr = "127.0.0.1:0".parse().unwrap();
-    let bound_addr = start_server(addr, state, AUTH_TOKEN.to_string())
-        .await
-        .unwrap();
+    let bound_addr = start_server(addr, state, auth).await.unwrap();
 
     let url = format!("http://{}/v1/chat/completions", bound_addr);
     let resp = client()
@@ -741,9 +751,10 @@ async fn test_chat_completions_body_too_large() {
     let state = ironclaw::channels::web::test_helpers::TestGatewayBuilder::new()
         .llm_provider(llm_provider)
         .build();
-    let auth_state = ironclaw::channels::web::auth::AuthState {
-        token: AUTH_TOKEN.to_string(),
-    };
+    let auth_state = ironclaw::channels::web::auth::MultiAuthState::single(
+        AUTH_TOKEN.to_string(),
+        "test-user".to_string(),
+    );
 
     let app = Router::new()
         .route(

tests/support/gateway_workflow_harness.rs

@@ -13,8 +13,11 @@ use ironclaw::agent::routine_engine::RoutineEngine;
 use ironclaw::agent::{Agent, AgentDeps, SessionManager as AgentSessionManager};
 use ironclaw::app::{AppBuilder, AppBuilderFlags};
 use ironclaw::channels::IncomingMessage;
+use ironclaw::channels::web::auth::MultiAuthState;
 use ironclaw::channels::web::log_layer::LogBroadcaster;
-use ironclaw::channels::web::server::{GatewayState, RateLimiter, start_server};
+use ironclaw::channels::web::server::{
+    GatewayState, PerUserRateLimiter, RateLimiter, start_server,
+};
 use ironclaw::channels::web::sse::SseManager;
 use ironclaw::channels::web::ws::WsConnectionTracker;
 use ironclaw::config::{Config, RegistryProviderConfig, RoutineConfig};
@@ -211,8 +214,9 @@ impl GatewayWorkflowHarness {
 
         let gateway_state = Arc::new(GatewayState {
             msg_tx: tokio::sync::RwLock::new(Some(gw_tx)),
-            sse: SseManager::new(),
+            sse: Arc::new(SseManager::new()),
             workspace: components.workspace.clone(),
+            workspace_pool: None,
             session_manager: Some(Arc::clone(&agent_session_manager)),
             log_broadcaster: None,
             log_level_handle: None,
@@ -222,13 +226,14 @@ impl GatewayWorkflowHarness {
             job_manager: None,
             prompt_queue: None,
             scheduler: Some(scheduler_slot.clone()),
-            user_id: user_id.clone(),
+            owner_id: user_id.clone(),
+            default_sender_id: user_id.clone(),
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
             llm_provider: Some(Arc::clone(&components.llm)),
             skill_registry: components.skill_registry.clone(),
             skill_catalog: components.skill_catalog.clone(),
-            chat_rate_limiter: RateLimiter::new(120, 60),
+            chat_rate_limiter: PerUserRateLimiter::new(120, 60),
             oauth_rate_limiter: RateLimiter::new(10, 60),
             webhook_rate_limiter: RateLimiter::new(10, 60),
             registry_entries: Vec::new(),
@@ -254,12 +259,13 @@ impl GatewayWorkflowHarness {
                 skills_config: components.config.skills.clone(),
                 hooks: components.hooks,
                 cost_guard: components.cost_guard,
-                sse_tx: Some(gateway_state.sse.sender()),
+                sse_tx: None,
                 http_interceptor: None,
                 transcription: None,
                 document_extraction: None,
                 sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
                 builder: None,
+                llm_backend: "nearai".to_string(),
             },
             channels,
             None,
@@ -288,10 +294,11 @@ impl GatewayWorkflowHarness {
         }
 
         let auth_token = "gateway-test-token".to_string();
+        let auth = MultiAuthState::single(auth_token.clone(), user_id.clone());
         let addr = start_server(
             "127.0.0.1:0".parse().expect("valid localhost addr"),
             Arc::clone(&gateway_state),
-            auth_token.clone(),
+            auth,
         )
         .await
         .expect("failed to start gateway server");

tests/support/test_rig.rs

@@ -701,7 +701,7 @@ impl TestRigBuilder {
                     let wasm_bytes = tokio::fs::read(&spec.wasm_path)
                         .await
                         .unwrap_or_else(|e| panic!("read {}: {e}", spec.wasm_path.display()));
-                    let (capabilities, description, schema) =
+                    let (capabilities, description) =
                         if let Some(cap_path) = &spec.capabilities_path {
                             if cap_path.exists() {
                                 let cap_bytes = tokio::fs::read(cap_path)
@@ -709,16 +709,12 @@ impl TestRigBuilder {
                                     .unwrap_or_else(|e| panic!("read {}: {e}", cap_path.display()));
                                 let cap_file = CapabilitiesFile::from_bytes(&cap_bytes)
                                     .expect("parse capabilities.json");
-                                (
-                                    cap_file.to_capabilities(),
-                                    cap_file.description.clone(),
-                                    cap_file.parameters.clone(),
-                                )
+                                (cap_file.to_capabilities(), cap_file.description.clone())
                             } else {
-                                (Capabilities::default(), None, None)
+                                (Capabilities::default(), None)
                             }
                         } else {
-                            (Capabilities::default(), None, None)
+                            (Capabilities::default(), None)
                         };
 
                     let prepared = runtime
@@ -730,9 +726,6 @@ impl TestRigBuilder {
                     if let Some(desc) = description {
                         wrapper = wrapper.with_description(desc);
                     }
-                    if let Some(s) = schema {
-                        wrapper = wrapper.with_schema(s);
-                    }
                     if let Some(interceptor) = &http_interceptor {
                         wrapper = wrapper.with_http_interceptor(Arc::clone(interceptor));
                     }
@@ -768,6 +761,7 @@ impl TestRigBuilder {
             document_extraction: None,
             sandbox_readiness: ironclaw::agent::SandboxReadiness::Available, // tests don't use real Docker
             builder: None,
+            llm_backend: "nearai".to_string(),
         };
 
         // 7. Create TestChannel and ChannelManager.

tests/ws_gateway_integration.rs

@@ -39,8 +39,9 @@ async fn start_test_server() -> (
 
     let state = Arc::new(GatewayState {
         msg_tx: tokio::sync::RwLock::new(Some(agent_tx)),
-        sse: SseManager::new(),
+        sse: Arc::new(SseManager::new()),
         workspace: None,
+        workspace_pool: None,
         session_manager: None,
         log_broadcaster: None,
         log_level_handle: None,
@@ -50,13 +51,14 @@ async fn start_test_server() -> (
         job_manager: None,
         prompt_queue: None,
         scheduler: None,
-        user_id: "test-user".to_string(),
+        owner_id: "test-user".to_string(),
+        default_sender_id: "test-user".to_string(),
         shutdown_tx: tokio::sync::RwLock::new(None),
         ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
         llm_provider: None,
         skill_registry: None,
         skill_catalog: None,
-        chat_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(30, 60),
+        chat_rate_limiter: ironclaw::channels::web::server::PerUserRateLimiter::new(30, 60),
         oauth_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         webhook_rate_limiter: ironclaw::channels::web::server::RateLimiter::new(10, 60),
         registry_entries: Vec::new(),
@@ -66,8 +68,12 @@ async fn start_test_server() -> (
         active_config: ironclaw::channels::web::server::ActiveConfigSnapshot::default(),
     });
 
+    let auth = ironclaw::channels::web::auth::MultiAuthState::single(
+        AUTH_TOKEN.to_string(),
+        "test-user".to_string(),
+    );
     let addr: SocketAddr = "127.0.0.1:0".parse().unwrap();
-    let bound_addr = start_server(addr, state.clone(), AUTH_TOKEN.to_string())
+    let bound_addr = start_server(addr, state.clone(), auth)
         .await
         .expect("Failed to start test server");
 

tools-src/github/github-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.1",
   "wit_version": "0.3.0",
+  "description": "Manage GitHub repositories, issues, pull requests, reviews, and workflows. Supports listing, creating, commenting, merging PRs, and triggering GitHub Actions.",
   "capabilities": {
     "webhook": {
       "hmac_secret_name": "github_webhook_secret",

tools-src/gmail/gmail-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Read, search, send, draft, and reply to emails via Gmail. Supports Gmail search query syntax (is:unread, from:, subject:, after:, etc.).",
   "http": {
     "allowlist": [
       {
@@ -53,7 +54,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/google-calendar/google-calendar-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "View, create, update, and delete Google Calendar events. Supports timed events, all-day events, attendees, locations, and free text search.",
   "http": {
     "allowlist": [
       {
@@ -52,7 +53,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/google-docs/google-docs-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Create, read, edit, and format Google Docs documents. Supports text insert/delete/replace, formatting (bold, italic, font, color, size), paragraph styling, tables, and lists.",
   "http": {
     "allowlist": [
       {
@@ -52,7 +53,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/google-drive/google-drive-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Search, access, upload, share, and organize files and folders in Google Drive. Supports personal drives and shared (organizational) drives.",
   "http": {
     "allowlist": [
       {
@@ -57,7 +58,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/google-sheets/google-sheets-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Create, read, write, and format Google Sheets spreadsheets. Supports cell operations using A1 notation, sheet (tab) management, and cell formatting.",
   "http": {
     "allowlist": [
       {
@@ -52,7 +53,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/google-slides/google-slides-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Create, read, edit, and format Google Slides presentations. Supports slide management, text operations, shapes, images, text formatting, and paragraph alignment.",
   "http": {
     "allowlist": [
       {
@@ -52,7 +53,7 @@
       },
       {
         "name": "google_oauth_client_secret",
-        "prompt": "Google OAuth Client Secret"
+        "prompt": "Google OAuth Client Secret (from console.cloud.google.com/apis/credentials)"
       }
     ]
   }

tools-src/llm-context/llm-context-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.1.0",
   "wit_version": "0.3.0",
+  "description": "Fetch pre-extracted web content from Brave Search for grounding LLM answers. Returns actual page content (text chunks, tables, code) relevant to the query, ready for RAG or fact-checking.",
   "capabilities": {
     "http": {
       "allowlist": [

tools-src/slack/slack-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Send messages, list channels, read history, add reactions, and get user information in Slack.",
   "http": {
     "allowlist": [
       {
@@ -57,7 +58,7 @@
       },
       {
         "name": "slack_oauth_client_secret",
-        "prompt": "Slack OAuth Client Secret"
+        "prompt": "Slack OAuth Client Secret (from api.slack.com/apps > Basic Information)"
       }
     ]
   }

tools-src/telegram/telegram-tool.capabilities.json

@@ -1,6 +1,7 @@
 {
   "version": "0.2.0",
   "wit_version": "0.3.0",
+  "description": "Read and send messages from a Telegram user account. Supports contacts, chat history, message search, sending, forwarding, and deletion via encrypted MTProto.",
   "http": {
     "allowlist": [
       {
@@ -35,7 +36,7 @@
       },
       {
         "name": "telegram_api_hash",
-        "prompt": "Telegram API Hash"
+        "prompt": "Telegram API Hash (from my.telegram.org/apps — alphanumeric string)"
       }
     ]
   }

tools-src/web-search/web-search-tool.capabilities.json

@@ -2,40 +2,6 @@
   "version": "0.2.0",
   "wit_version": "0.3.0",
   "description": "Search the web using Brave Search. Returns titles, URLs, descriptions, and publication dates for matching web pages. Supports filtering by country, language, and freshness. Authentication is handled via the 'brave_api_key' secret injected by the host.",
-  "parameters": {
-    "type": "object",
-    "properties": {
-      "query": {
-        "type": "string",
-        "description": "The search query to look up on the web"
-      },
-      "count": {
-        "type": "integer",
-        "description": "Number of results to return (1-20, default 5)",
-        "minimum": 1,
-        "maximum": 20,
-        "default": 5
-      },
-      "country": {
-        "type": "string",
-        "description": "2-letter uppercase country code to bias results (e.g. 'US', 'DE', 'JP')"
-      },
-      "search_lang": {
-        "type": "string",
-        "description": "2-letter lowercase language code for search results (e.g. 'en', 'de', 'fr')"
-      },
-      "ui_lang": {
-        "type": "string",
-        "description": "Locale in language-region format (e.g. 'en-US', 'de-DE')"
-      },
-      "freshness": {
-        "type": "string",
-        "description": "Filter by discovery time: 'pd' (past day), 'pw' (past week), 'pm' (past month), 'py' (past year), or date range 'YYYY-MM-DDtoYYYY-MM-DD'"
-      }
-    },
-    "required": ["query"],
-    "additionalProperties": false
-  },
   "capabilities": {
     "http": {
       "allowlist": [