Merge pull request #1422 from nearai/staging-promote/71f41dd1-23309993684

chore: promote staging to staging-promote/71f9012d-23307625134 (2026-03-19 18:14 UTC)

FEATURE_PARITY.md

@@ -465,7 +465,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Device pairing | ✅ | ❌ | |
 | Tailscale identity | ✅ | ❌ | |
 | Trusted-proxy auth | ✅ | ❌ | Header-based reverse proxy auth |
-| OAuth flows | ✅ | 🚧 | NEAR AI OAuth |
+| OAuth flows | ✅ | 🚧 | NEAR AI OAuth plus hosted extension/MCP OAuth broker; external auth-proxy rollout still pending |
 | DM pairing verification | ✅ | ✅ | ironclaw pairing approve, host APIs |
 | Allowlist/blocklist | ✅ | 🚧 | allow_from + pairing store |
 | Per-group tool policies | ✅ | ❌ | |

channels-src/feishu/src/lib.rs

@@ -206,9 +206,17 @@ struct FeishuApiResponse<T> {
     data: Option<T>,
 }
 
-/// Tenant access token response.
-#[derive(Debug, Default, Deserialize)]
-struct TenantAccessTokenData {
+/// Tenant access token response (flat format).
+///
+/// Unlike most Feishu APIs that nest results under `data`, the
+/// `/auth/v3/tenant_access_token/internal` endpoint returns `code`, `msg`,
+/// `tenant_access_token`, and `expire` at the top level.
+#[derive(Debug, Deserialize)]
+struct TenantAccessTokenResponse {
+    #[serde(default)]
+    code: i32,
+    #[serde(default)]
+    msg: String,
     tenant_access_token: String,
     expire: i64,
 }
@@ -770,9 +778,8 @@ fn obtain_tenant_token(api_base: &str) -> Result<String, String> {
                 ));
             }
 
-            let token_resp: FeishuApiResponse<TenantAccessTokenData> =
-                serde_json::from_slice(&response.body)
-                    .map_err(|e| format!("Failed to parse token response: {}", e))?;
+            let token_resp: TenantAccessTokenResponse = serde_json::from_slice(&response.body)
+                .map_err(|e| format!("Failed to parse token response: {}", e))?;
 
             if token_resp.code != 0 {
                 return Err(format!(
@@ -781,23 +788,33 @@ fn obtain_tenant_token(api_base: &str) -> Result<String, String> {
                 ));
             }
 
-            let data = token_resp
-                .data
-                .ok_or_else(|| "Token response missing data".to_string())?;
+            if token_resp.tenant_access_token.is_empty() {
+                return Err("Token response missing tenant_access_token".to_string());
+            }
+
+            if token_resp.expire <= 0 {
+                return Err(format!(
+                    "Token response has invalid expire value: {}",
+                    token_resp.expire
+                ));
+            }
 
             // Cache the token with expiry.
             let now = channel_host::now_millis();
-            let expiry = now + (data.expire as u64) * 1000;
+            let expiry = now.saturating_add((token_resp.expire as u64).saturating_mul(1000));
 
-            let _ = channel_host::workspace_write(TOKEN_PATH, &data.tenant_access_token);
+            let _ = channel_host::workspace_write(TOKEN_PATH, &token_resp.tenant_access_token);
             let _ = channel_host::workspace_write(TOKEN_EXPIRY_PATH, &expiry.to_string());
 
             channel_host::log(
                 channel_host::LogLevel::Debug,
-                &format!("Tenant access token refreshed, expires in {}s", data.expire),
+                &format!(
+                    "Tenant access token refreshed, expires in {}s",
+                    token_resp.expire
+                ),
             );
 
-            Ok(data.tenant_access_token)
+            Ok(token_resp.tenant_access_token)
         }
         Err(e) => Err(format!("Token exchange request failed: {}", e)),
     }
@@ -819,3 +836,60 @@ fn json_response(status: u16, body: serde_json::Value) -> OutgoingHttpResponse {
         body: body_bytes,
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn parse_flat_token_response() {
+        let json = r#"{
+            "code": 0,
+            "msg": "ok",
+            "tenant_access_token": "t-abc123",
+            "expire": 7200
+        }"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 0);
+        assert_eq!(resp.msg, "ok");
+        assert_eq!(resp.tenant_access_token, "t-abc123");
+        assert_eq!(resp.expire, 7200);
+    }
+
+    #[test]
+    fn parse_token_response_rejects_missing_token() {
+        let json = r#"{"code": 0, "msg": "ok", "expire": 7200}"#;
+        let result: Result<TenantAccessTokenResponse, _> = serde_json::from_str(json);
+        assert!(result.is_err(), "should fail when tenant_access_token is missing");
+    }
+
+    #[test]
+    fn parse_token_response_rejects_missing_expire() {
+        let json = r#"{"code": 0, "msg": "ok", "tenant_access_token": "t-abc"}"#;
+        let result: Result<TenantAccessTokenResponse, _> = serde_json::from_str(json);
+        assert!(result.is_err(), "should fail when expire is missing");
+    }
+
+    #[test]
+    fn parse_token_response_defaults_code_and_msg() {
+        let json = r#"{"tenant_access_token": "t-abc", "expire": 3600}"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 0);
+        assert_eq!(resp.msg, "");
+        assert_eq!(resp.tenant_access_token, "t-abc");
+        assert_eq!(resp.expire, 3600);
+    }
+
+    #[test]
+    fn parse_token_error_response() {
+        let json = r#"{
+            "code": 10003,
+            "msg": "invalid app_id",
+            "tenant_access_token": "",
+            "expire": 0
+        }"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 10003);
+        assert!(resp.tenant_access_token.is_empty());
+    }
+}

src/agent/dispatcher.rs

@@ -29,7 +29,7 @@ pub(super) enum AgenticLoopResult {
     /// A tool requires approval before continuing.
     NeedApproval {
         /// The pending approval request to store.
-        pending: PendingApproval,
+        pending: Box<PendingApproval>,
     },
 }
 
@@ -217,9 +217,7 @@ impl Agent {
                 reason: format!("Exceeded maximum tool iterations ({max_tool_iterations})"),
             }
             .into()),
-            LoopOutcome::NeedApproval(pending) => {
-                Ok(AgenticLoopResult::NeedApproval { pending: *pending })
-            }
+            LoopOutcome::NeedApproval(pending) => Ok(AgenticLoopResult::NeedApproval { pending }),
         }
     }
 
@@ -482,6 +480,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
             usize,
             crate::llm::ToolCall,
             Arc<dyn crate::tools::Tool>,
+            bool, // allow_always
         )> = None;
 
         for (idx, original_tc) in tool_calls.iter().enumerate() {
@@ -551,7 +550,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                 && let Some(tool) = tool_opt
             {
                 use crate::tools::ApprovalRequirement;
-                let needs_approval = match tool.requires_approval(&tc.arguments) {
+                let requirement = tool.requires_approval(&tc.arguments);
+                let needs_approval = match requirement {
                     ApprovalRequirement::Never => false,
                     ApprovalRequirement::UnlessAutoApproved => {
                         let sess = self.session.lock().await;
@@ -586,7 +586,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                         continue;
                     }
 
-                    approval_needed = Some((idx, tc, tool));
+                    let allow_always = !matches!(requirement, ApprovalRequirement::Always);
+                    approval_needed = Some((idx, tc, tool, allow_always));
                     break;
                 }
             }
@@ -887,7 +888,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
         }
 
         // Handle approval if a tool needed it
-        if let Some((approval_idx, tc, tool)) = approval_needed {
+        if let Some((approval_idx, tc, tool, allow_always)) = approval_needed {
             let display_params = redact_params(&tc.arguments, tool.sensitive_params());
             let pending = PendingApproval {
                 request_id: Uuid::new_v4(),
@@ -899,6 +900,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                 context_messages: reason_ctx.messages.clone(),
                 deferred_tool_calls: tool_calls[approval_idx + 1..].to_vec(),
                 user_timezone: Some(self.user_tz.name().to_string()),
+                allow_always,
             };
 
             return Ok(Some(LoopOutcome::NeedApproval(Box::new(pending))));
@@ -1365,6 +1367,35 @@ mod tests {
         assert!(always_needs, "Always must always require approval");
     }
 
+    /// Regression test: `allow_always` must be `false` for `Always` and
+    /// `true` for `UnlessAutoApproved`, so the UI hides the "always" button
+    /// for tools that truly cannot be auto-approved.
+    #[test]
+    fn test_allow_always_matches_approval_requirement() {
+        use crate::tools::ApprovalRequirement;
+
+        // Mirrors the expression used in dispatcher.rs and thread_ops.rs:
+        //   let allow_always = !matches!(requirement, ApprovalRequirement::Always);
+
+        // UnlessAutoApproved → allow_always = true
+        let req = ApprovalRequirement::UnlessAutoApproved;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(
+            allow_always,
+            "UnlessAutoApproved should set allow_always = true"
+        );
+
+        // Always → allow_always = false
+        let req = ApprovalRequirement::Always;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(!allow_always, "Always should set allow_always = false");
+
+        // Never → allow_always = true (approval is never needed, but if it were, always would be ok)
+        let req = ApprovalRequirement::Never;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(allow_always, "Never should set allow_always = true");
+    }
+
     #[test]
     fn test_pending_approval_serialization_backcompat_without_deferred_calls() {
         // PendingApproval from before the deferred_tool_calls field was added
@@ -1410,6 +1441,7 @@ mod tests {
                 },
             ],
             user_timezone: None,
+            allow_always: true,
         };
 
         let json = serde_json::to_string(&pending).expect("serialize");

src/agent/job_monitor.rs

@@ -211,6 +211,7 @@ mod tests {
                     job_id: job_id.to_string(),
                     status: "completed".to_string(),
                     session_id: None,
+                    fallback_deliverable: None,
                 },
             ))
             .unwrap();

src/agent/session.rs

@@ -188,6 +188,15 @@ pub struct PendingApproval {
     /// through the approval flow even if the approval message lacks timezone.
     #[serde(default)]
     pub user_timezone: Option<String>,
+    /// Whether the "always" auto-approve option should be offered to the user.
+    /// `false` when the tool returned `ApprovalRequirement::Always` (e.g.
+    /// destructive shell commands), meaning every invocation must be confirmed.
+    #[serde(default = "default_true")]
+    pub allow_always: bool,
+}
+
+fn default_true() -> bool {
+    true
 }
 
 /// A conversation thread within a session.
@@ -1106,6 +1115,7 @@ mod tests {
             context_messages: vec![ChatMessage::user("do it")],
             deferred_tool_calls: vec![],
             user_timezone: None,
+            allow_always: false,
         };
 
         thread.await_approval(approval);
@@ -1132,6 +1142,7 @@ mod tests {
             context_messages: vec![],
             deferred_tool_calls: vec![],
             user_timezone: None,
+            allow_always: true,
         };
 
         thread.await_approval(approval);

src/agent/submission.rs

@@ -382,6 +382,8 @@ pub enum SubmissionResult {
         description: String,
         /// Parameters being passed.
         parameters: serde_json::Value,
+        /// Whether "always" auto-approve should be offered to the user.
+        allow_always: bool,
     },
 
     /// Successfully processed (for control commands).

src/agent/thread_ops.rs

@@ -506,7 +506,8 @@ impl Agent {
                 let tool_name = pending.tool_name.clone();
                 let description = pending.description.clone();
                 let parameters = pending.display_parameters.clone();
-                thread.await_approval(pending);
+                let allow_always = pending.allow_always;
+                thread.await_approval(*pending);
                 let _ = self
                     .channels
                     .send_status(
@@ -516,6 +517,7 @@ impl Agent {
                             tool_name: tool_name.clone(),
                             description: description.clone(),
                             parameters: parameters.clone(),
+                            allow_always,
                         },
                         &message.metadata,
                     )
@@ -525,6 +527,7 @@ impl Agent {
                     tool_name,
                     description,
                     parameters,
+                    allow_always,
                 })
             }
             Err(e) => {
@@ -1069,28 +1072,31 @@ impl Agent {
                 usize,
                 crate::llm::ToolCall,
                 Arc<dyn crate::tools::Tool>,
+                bool, // allow_always
             )> = None;
 
             for (idx, tc) in deferred_tool_calls.iter().enumerate() {
                 if let Some(tool) = self.tools().get(&tc.name).await {
                     // Match dispatcher.rs: when auto_approve_tools is true, skip
                     // all approval checks (including ApprovalRequirement::Always).
-                    let needs_approval = if self.config.auto_approve_tools {
-                        false
+                    let (needs_approval, allow_always) = if self.config.auto_approve_tools {
+                        (false, true)
                     } else {
                         use crate::tools::ApprovalRequirement;
-                        match tool.requires_approval(&tc.arguments) {
+                        let requirement = tool.requires_approval(&tc.arguments);
+                        let needs = match requirement {
                             ApprovalRequirement::Never => false,
                             ApprovalRequirement::UnlessAutoApproved => {
                                 let sess = session.lock().await;
                                 !sess.is_tool_auto_approved(&tc.name)
                             }
                             ApprovalRequirement::Always => true,
-                        }
+                        };
+                        (needs, !matches!(requirement, ApprovalRequirement::Always))
                     };
 
                     if needs_approval {
-                        approval_needed = Some((idx, tc.clone(), tool));
+                        approval_needed = Some((idx, tc.clone(), tool, allow_always));
                         break; // remaining tools stay deferred
                     }
                 }
@@ -1298,7 +1304,7 @@ impl Agent {
             }
 
             // Handle approval if a tool needed it
-            if let Some((approval_idx, tc, tool)) = approval_needed {
+            if let Some((approval_idx, tc, tool, allow_always)) = approval_needed {
                 let new_pending = PendingApproval {
                     request_id: Uuid::new_v4(),
                     tool_name: tc.name.clone(),
@@ -1310,6 +1316,7 @@ impl Agent {
                     deferred_tool_calls: deferred_tool_calls[approval_idx + 1..].to_vec(),
                     // Carry forward the resolved timezone from the original pending approval
                     user_timezone: pending.user_timezone.clone(),
+                    allow_always,
                 };
 
                 let request_id = new_pending.request_id;
@@ -1333,6 +1340,7 @@ impl Agent {
                             tool_name: tool_name.clone(),
                             description: description.clone(),
                             parameters: parameters.clone(),
+                            allow_always,
                         },
                         &message.metadata,
                     )
@@ -1343,6 +1351,7 @@ impl Agent {
                     tool_name,
                     description,
                     parameters,
+                    allow_always,
                 });
             }
 
@@ -1411,7 +1420,8 @@ impl Agent {
                     let tool_name = new_pending.tool_name.clone();
                     let description = new_pending.description.clone();
                     let parameters = new_pending.display_parameters.clone();
-                    thread.await_approval(new_pending);
+                    let allow_always = new_pending.allow_always;
+                    thread.await_approval(*new_pending);
                     let _ = self
                         .channels
                         .send_status(
@@ -1421,6 +1431,7 @@ impl Agent {
                                 tool_name: tool_name.clone(),
                                 description: description.clone(),
                                 parameters: parameters.clone(),
+                                allow_always,
                             },
                             &message.metadata,
                         )
@@ -1430,6 +1441,7 @@ impl Agent {
                         tool_name,
                         description,
                         parameters,
+                        allow_always,
                     })
                 }
                 Err(e) => {
@@ -1949,6 +1961,7 @@ mod tests {
             context_messages: vec![],
             deferred_tool_calls: vec![],
             user_timezone: None,
+            allow_always: false,
         };
         thread.await_approval(pending);
 

src/app.rs

@@ -25,7 +25,7 @@ use crate::tools::ToolRegistry;
 use crate::tools::mcp::{McpProcessManager, McpSessionManager};
 use crate::tools::wasm::SharedCredentialRegistry;
 use crate::tools::wasm::WasmToolRuntime;
-use crate::workspace::{EmbeddingProvider, Workspace};
+use crate::workspace::{EmbeddingCacheConfig, EmbeddingProvider, Workspace};
 
 /// Fully initialized application components, ready for channel wiring
 /// and agent construction.
@@ -313,10 +313,13 @@ impl AppBuilder {
 
         // Register memory tools if database is available
         let workspace = if let Some(ref db) = self.db {
+            let emb_cache_config = EmbeddingCacheConfig {
+                max_entries: self.config.embeddings.cache_size,
+            };
             let mut ws = Workspace::new_with_db(&self.config.owner_id, db.clone())
                 .with_search_config(&self.config.search);
             if let Some(ref emb) = embeddings {
-                ws = ws.with_embeddings(emb.clone());
+                ws = ws.with_embeddings_cached(emb.clone(), emb_cache_config);
             }
             let ws = Arc::new(ws);
             tools.register_memory_tools(Arc::clone(&ws));

src/channels/channel.rs

@@ -305,6 +305,11 @@ pub enum StatusUpdate {
         tool_name: String,
         description: String,
         parameters: serde_json::Value,
+        /// When `true`, the UI should offer an "always" option that auto-approves
+        /// future calls to this tool for the rest of the session.  When `false`
+        /// (i.e. `ApprovalRequirement::Always`), the tool must be approved every
+        /// time and the "always" button should be hidden.
+        allow_always: bool,
     },
     /// Extension needs user authentication (token or OAuth).
     AuthRequired {

src/channels/manager.rs

@@ -239,6 +239,11 @@ impl ChannelManager {
     pub async fn get_channel(&self, name: &str) -> Option<Arc<dyn Channel>> {
         self.channels.read().await.get(name).cloned()
     }
+
+    /// Remove a channel from the manager.
+    pub async fn remove(&self, name: &str) -> Option<Arc<dyn Channel>> {
+        self.channels.write().await.remove(name)
+    }
 }
 
 impl Default for ChannelManager {

src/channels/relay/channel.rs

@@ -1,16 +1,16 @@
-//! Channel trait implementation for channel-relay SSE streams.
+//! Channel trait implementation for channel-relay webhook callbacks.
 //!
-//! `RelayChannel` connects to a channel-relay service via SSE, converts
-//! incoming events to `IncomingMessage`s, and sends responses via the
-//! relay's provider-specific proxy API (Slack).
+//! `RelayChannel` receives events from channel-relay via HTTP POST callbacks
+//! (pushed through an mpsc channel by the webhook handler), converts them
+//! to `IncomingMessage`s, and sends responses via the relay's provider-specific
+//! proxy API (Slack).
 
 use std::collections::HashMap;
-use std::sync::Arc;
 
 use async_trait::async_trait;
-use tokio::sync::{RwLock, mpsc};
+use tokio::sync::mpsc;
 
-use crate::channels::relay::client::{RelayClient, RelayError};
+use crate::channels::relay::client::{ChannelEvent, RelayClient};
 use crate::channels::{Channel, IncomingMessage, MessageStream, OutgoingResponse, StatusUpdate};
 use crate::error::ChannelError;
 
@@ -39,44 +39,34 @@ impl RelayProvider {
     }
 }
 
-/// Channel implementation that connects to a channel-relay SSE stream.
+/// Channel implementation that receives events from channel-relay via webhook callbacks.
 pub struct RelayChannel {
     client: RelayClient,
     provider: RelayProvider,
-    stream_token: Arc<RwLock<String>>,
     team_id: String,
     instance_id: String,
-    user_id: String,
-    /// SSE stream long-poll timeout in seconds.
-    stream_timeout_secs: u64,
-    /// Initial exponential backoff in milliseconds.
-    backoff_initial_ms: u64,
-    /// Maximum exponential backoff in milliseconds.
-    backoff_max_ms: u64,
-    /// Handle to the reconnect task for clean shutdown.
-    reconnect_handle: RwLock<Option<tokio::task::JoinHandle<()>>>,
-    /// Handle to the SSE parser task for clean shutdown.
-    parser_handle: Arc<RwLock<Option<tokio::task::JoinHandle<()>>>>,
-    /// Maximum consecutive reconnect failures before giving up.
-    max_consecutive_failures: u64,
+    /// Sender side of the event channel — shared with the webhook handler.
+    event_tx: mpsc::Sender<ChannelEvent>,
+    /// Receiver side — taken once by `start()`.
+    event_rx: tokio::sync::Mutex<Option<mpsc::Receiver<ChannelEvent>>>,
 }
 
 impl RelayChannel {
     /// Create a new relay channel for Slack (default provider).
     pub fn new(
         client: RelayClient,
-        stream_token: String,
         team_id: String,
         instance_id: String,
-        user_id: String,
+        event_tx: mpsc::Sender<ChannelEvent>,
+        event_rx: mpsc::Receiver<ChannelEvent>,
     ) -> Self {
         Self::new_with_provider(
             client,
             RelayProvider::Slack,
-            stream_token,
             team_id,
             instance_id,
-            user_id,
+            event_tx,
+            event_rx,
         )
     }
 
@@ -84,44 +74,24 @@ impl RelayChannel {
     pub fn new_with_provider(
         client: RelayClient,
         provider: RelayProvider,
-        stream_token: String,
         team_id: String,
         instance_id: String,
-        user_id: String,
+        event_tx: mpsc::Sender<ChannelEvent>,
+        event_rx: mpsc::Receiver<ChannelEvent>,
     ) -> Self {
         Self {
             client,
             provider,
-            stream_token: Arc::new(RwLock::new(stream_token)),
             team_id,
             instance_id,
-            user_id,
-            stream_timeout_secs: 86400,
-            backoff_initial_ms: 1000,
-            backoff_max_ms: 60000,
-            reconnect_handle: RwLock::new(None),
-            parser_handle: Arc::new(RwLock::new(None)),
-            max_consecutive_failures: 50,
+            event_tx,
+            event_rx: tokio::sync::Mutex::new(Some(event_rx)),
         }
     }
 
-    /// Set backoff/timeout parameters from relay config values.
-    pub fn with_timeouts(
-        mut self,
-        stream_timeout_secs: u64,
-        backoff_initial_ms: u64,
-        backoff_max_ms: u64,
-    ) -> Self {
-        self.stream_timeout_secs = stream_timeout_secs;
-        self.backoff_initial_ms = backoff_initial_ms;
-        self.backoff_max_ms = backoff_max_ms;
-        self
-    }
-
-    /// Set the maximum number of consecutive reconnect failures before giving up.
-    pub fn with_max_failures(mut self, max: u64) -> Self {
-        self.max_consecutive_failures = max;
-        self
+    /// Get a clone of the event sender for wiring into the webhook endpoint.
+    pub fn event_sender(&self) -> mpsc::Sender<ChannelEvent> {
+        self.event_tx.clone()
     }
 
     /// Build a provider-appropriate proxy body for sending a message.
@@ -151,15 +121,9 @@ impl RelayChannel {
         team_id: &str,
         method: &str,
         body: serde_json::Value,
-    ) -> Result<serde_json::Value, RelayError> {
+    ) -> Result<serde_json::Value, crate::channels::relay::client::RelayError> {
         self.client
-            .proxy_provider(
-                self.provider.as_str(),
-                team_id,
-                method,
-                body,
-                Some(&self.instance_id),
-            )
+            .proxy_provider(self.provider.as_str(), team_id, method, body)
             .await
     }
 }
@@ -172,204 +136,82 @@ impl Channel for RelayChannel {
 
     async fn start(&self) -> Result<MessageStream, ChannelError> {
         let channel_name = self.name().to_string();
-        let token = self.stream_token.read().await.clone();
-        let (stream, initial_parser_handle) = self
-            .client
-            .connect_stream(&token, self.stream_timeout_secs)
-            .await
-            .map_err(|e| ChannelError::StartupFailed {
-                name: channel_name.clone(),
-                reason: e.to_string(),
-            })?;
 
-        *self.parser_handle.write().await = Some(initial_parser_handle);
+        // Take the receiver (can only start once)
+        let mut event_rx =
+            self.event_rx
+                .lock()
+                .await
+                .take()
+                .ok_or_else(|| ChannelError::StartupFailed {
+                    name: channel_name.clone(),
+                    reason: "RelayChannel already started".to_string(),
+                })?;
 
         let (tx, rx) = mpsc::channel(64);
-
-        // Spawn the stream reader + reconnect task
-        let client = self.client.clone();
-        let stream_token = Arc::clone(&self.stream_token);
-        let instance_id = self.instance_id.clone();
-        let user_id = self.user_id.clone();
-        let team_id = self.team_id.clone();
-        let stream_timeout_secs = self.stream_timeout_secs;
-        let backoff_initial_ms = self.backoff_initial_ms;
-        let backoff_max_ms = self.backoff_max_ms;
-        let max_consecutive_failures = self.max_consecutive_failures;
-        let parser_handle = Arc::clone(&self.parser_handle);
         let provider_str = self.provider.as_str().to_string();
         let relay_name = channel_name.clone();
 
-        let handle = tokio::spawn(async move {
-            use futures::StreamExt;
-
-            let mut current_stream = stream;
-            let mut backoff_ms = backoff_initial_ms;
-            let mut consecutive_failures: u64 = 0;
-
-            loop {
-                // Read events from the current stream
-                while let Some(event) = current_stream.next().await {
-                    // Reset backoff and failure count on successful event
-                    backoff_ms = backoff_initial_ms;
-                    consecutive_failures = 0;
-
-                    // Validate required fields
-                    if event.sender_id.is_empty()
-                        || event.channel_id.is_empty()
-                        || event.provider_scope.is_empty()
-                    {
-                        tracing::debug!(
-                            event_type = %event.event_type,
-                            sender_id = %event.sender_id,
-                            channel_id = %event.channel_id,
-                            "Relay: skipping event with missing required fields"
-                        );
-                        continue;
-                    }
-
-                    // Skip non-message events
-                    if !event.is_message() {
-                        tracing::debug!(
-                            event_type = %event.event_type,
-                            "Relay: skipping non-message event"
-                        );
-                        continue;
-                    }
-
-                    tracing::info!(
+        // Spawn a task that reads events from the webhook handler and converts to IncomingMessage
+        tokio::spawn(async move {
+            while let Some(event) = event_rx.recv().await {
+                // Validate required fields
+                if event.sender_id.is_empty()
+                    || event.channel_id.is_empty()
+                    || event.provider_scope.is_empty()
+                {
+                    tracing::debug!(
                         event_type = %event.event_type,
-                        sender = %event.sender_id,
-                        channel = %event.channel_id,
-                        provider = %provider_str,
-                        "Relay: received message from {}", provider_str
+                        sender_id = %event.sender_id,
+                        channel_id = %event.channel_id,
+                        "Relay: skipping event with missing required fields"
                     );
-
-                    let msg = IncomingMessage::new(&relay_name, &event.sender_id, event.text())
-                        .with_user_name(event.display_name())
-                        .with_metadata(serde_json::json!({
-                            "team_id": event.team_id(),
-                            "channel_id": event.channel_id,
-                            "sender_id": event.sender_id,
-                            "sender_name": event.display_name(),
-                            "event_type": event.event_type,
-                            "thread_id": event.thread_id,
-                            "provider": event.provider,
-                        }));
-
-                    let msg = if let Some(ref thread_id) = event.thread_id {
-                        msg.with_thread(thread_id)
-                    } else {
-                        msg.with_thread(&event.channel_id)
-                    };
-
-                    if tx.send(msg).await.is_err() {
-                        tracing::info!("Relay channel receiver dropped, stopping");
-                        return;
-                    }
+                    continue;
                 }
 
-                // Stream ended, attempt reconnect with backoff
-                consecutive_failures += 1;
-                if consecutive_failures >= max_consecutive_failures {
-                    tracing::error!(
-                        channel = %relay_name,
-                        failures = consecutive_failures,
-                        "Relay channel giving up after {} consecutive failures",
-                        consecutive_failures
+                // Skip non-message events
+                if !event.is_message() {
+                    tracing::debug!(
+                        event_type = %event.event_type,
+                        "Relay: skipping non-message event"
                     );
-                    break;
+                    continue;
                 }
 
-                tracing::warn!(
-                    backoff_ms = backoff_ms,
-                    failures = consecutive_failures,
-                    "Relay SSE stream ended, reconnecting..."
+                tracing::info!(
+                    event_type = %event.event_type,
+                    sender = %event.sender_id,
+                    channel = %event.channel_id,
+                    provider = %provider_str,
+                    "Relay: received message from {}", provider_str
                 );
-                tokio::time::sleep(std::time::Duration::from_millis(backoff_ms)).await;
-                backoff_ms = (backoff_ms * 2).min(backoff_max_ms);
 
-                // Try to reconnect
-                let token = stream_token.read().await.clone();
-                match client.connect_stream(&token, stream_timeout_secs).await {
-                    Ok((new_stream, new_parser)) => {
-                        tracing::info!("Relay SSE stream reconnected");
-                        consecutive_failures = 0;
-                        backoff_ms = backoff_initial_ms;
-                        current_stream = new_stream;
-                        // Abort old parser before replacing
-                        if let Some(old) = parser_handle.write().await.take() {
-                            old.abort();
-                        }
-                        *parser_handle.write().await = Some(new_parser);
-                    }
-                    Err(RelayError::TokenExpired) => {
-                        // Attempt token renewal
-                        tracing::info!("Relay stream token expired, renewing...");
-                        match client.renew_token(&instance_id, &user_id).await {
-                            Ok(new_token) => {
-                                *stream_token.write().await = new_token.clone();
-                                match client.connect_stream(&new_token, stream_timeout_secs).await {
-                                    Ok((new_stream, new_parser)) => {
-                                        tracing::info!(
-                                            "Relay SSE stream reconnected with new token"
-                                        );
-                                        consecutive_failures = 0;
-                                        backoff_ms = backoff_initial_ms;
-                                        current_stream = new_stream;
-                                        if let Some(old) = parser_handle.write().await.take() {
-                                            old.abort();
-                                        }
-                                        *parser_handle.write().await = Some(new_parser);
-                                    }
-                                    Err(e) => {
-                                        tracing::error!(
-                                            error = %e,
-                                            "Failed to reconnect after token renewal"
-                                        );
-                                    }
-                                }
-                            }
-                            Err(e) => {
-                                tracing::error!(
-                                    error = %e,
-                                    "Failed to renew relay stream token"
-                                );
-                            }
-                        }
-                    }
-                    Err(e) => {
-                        tracing::error!(error = %e, "Failed to reconnect relay SSE stream");
-                    }
-                }
+                let msg = IncomingMessage::new(&relay_name, &event.sender_id, event.text())
+                    .with_user_name(event.display_name())
+                    .with_metadata(serde_json::json!({
+                        "team_id": event.team_id(),
+                        "channel_id": event.channel_id,
+                        "sender_id": event.sender_id,
+                        "sender_name": event.display_name(),
+                        "event_type": event.event_type,
+                        "thread_id": event.thread_id,
+                        "provider": event.provider,
+                    }));
 
-                // Check if the team is still valid (skip when team_id is unknown,
-                // e.g. when no DB store was available at activation time)
-                if !team_id.is_empty() {
-                    match client.list_connections(&instance_id).await {
-                        Ok(conns) => {
-                            let has_team =
-                                conns.iter().any(|c| c.team_id == team_id && c.connected);
-                            if !has_team {
-                                tracing::warn!(
-                                    team_id = %team_id,
-                                    "Team no longer connected, stopping relay channel"
-                                );
-                                return;
-                            }
-                        }
-                        Err(e) => {
-                            tracing::warn!(
-                                error = %e,
-                                "Could not verify team connection, will retry next iteration"
-                            );
-                        }
-                    }
+                let msg = if let Some(ref thread_id) = event.thread_id {
+                    msg.with_thread(thread_id)
+                } else {
+                    msg.with_thread(&event.channel_id)
+                };
+
+                if tx.send(msg).await.is_err() {
+                    tracing::info!("Relay channel receiver dropped, stopping");
+                    return;
                 }
             }
-        });
 
-        *self.reconnect_handle.write().await = Some(handle);
+            tracing::info!("Relay event channel closed");
+        });
 
         let stream = tokio_stream::wrappers::ReceiverStream::new(rx);
         Ok(Box::pin(stream))
@@ -423,6 +265,7 @@ impl Channel for RelayChannel {
             tool_name,
             description,
             parameters,
+            allow_always: _,
         } = status
         else {
             return Ok(());
@@ -450,28 +293,24 @@ impl Channel for RelayChannel {
                 name: self.name().to_string(),
                 reason: "Missing channel_id for approval buttons".into(),
             })?;
-        let sender_id = metadata
-            .get("sender_id")
-            .and_then(|v| v.as_str())
-            .ok_or_else(|| ChannelError::SendFailed {
-                name: self.name().to_string(),
-                reason: "Missing sender_id for approval buttons".into(),
-            })?;
         let thread_id = metadata.get("thread_id").and_then(|v| v.as_str());
         let team_id = metadata
             .get("team_id")
             .and_then(|v| v.as_str())
             .unwrap_or(&self.team_id);
 
-        // Button value payload (Slack limits button values to 2000 chars;
-        // safe with typical UUIDs but documented here as a constraint)
+        // Register server-side approval record and get opaque token.
+        // The button value contains ONLY the token — no routing fields.
+        let approval_token = self
+            .client
+            .create_approval(team_id, channel_id, thread_id, &request_id)
+            .await
+            .map_err(|e| ChannelError::SendFailed {
+                name: self.name().to_string(),
+                reason: format!("Failed to register approval: {e}"),
+            })?;
         let value_payload = serde_json::json!({
-            "instance_id": self.instance_id,
-            "team_id": team_id,
-            "channel_id": channel_id,
-            "thread_ts": thread_id,
-            "request_id": request_id,
-            "sender_id": sender_id,
+            "approval_token": approval_token,
         });
         let value_str = value_payload.to_string();
 
@@ -582,12 +421,8 @@ impl Channel for RelayChannel {
     }
 
     async fn shutdown(&self) -> Result<(), ChannelError> {
-        if let Some(handle) = self.reconnect_handle.write().await.take() {
-            handle.abort();
-        }
-        if let Some(handle) = self.parser_handle.write().await.take() {
-            handle.abort();
-        }
+        // Relay cleanup is driven by the extension manager dropping the shared
+        // sender and removing the channel from the channel manager.
         Ok(())
     }
 }
@@ -605,27 +440,20 @@ mod tests {
         .expect("client")
     }
 
+    fn make_channel() -> RelayChannel {
+        let (tx, rx) = mpsc::channel(64);
+        RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx, rx)
+    }
+
     #[test]
     fn relay_channel_name() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
         assert_eq!(channel.name(), DEFAULT_RELAY_NAME);
     }
 
     #[test]
     fn conversation_context_extracts_metadata() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
 
         let metadata = serde_json::json!({
             "sender_name": "bob",
@@ -640,8 +468,6 @@ mod tests {
 
     #[test]
     fn metadata_shape_includes_event_type_and_sender_name() {
-        // Regression: metadata JSON must include event_type and sender_name
-        // for downstream routing (DM vs channel) and conversation_context().
         let metadata = serde_json::json!({
             "team_id": "T123",
             "channel_id": "C456",
@@ -651,43 +477,19 @@ mod tests {
             "thread_id": null,
             "provider": "slack",
         });
-        // event_type must be present for DM-vs-channel routing
         assert_eq!(
             metadata.get("event_type").and_then(|v| v.as_str()),
             Some("direct_message")
         );
-        // sender_name must be present for conversation_context
         assert_eq!(
             metadata.get("sender_name").and_then(|v| v.as_str()),
             Some("alice")
         );
     }
 
-    #[test]
-    fn with_timeouts_sets_values() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        )
-        .with_timeouts(43200, 2000, 120000);
-
-        assert_eq!(channel.stream_timeout_secs, 43200);
-        assert_eq!(channel.backoff_initial_ms, 2000);
-        assert_eq!(channel.backoff_max_ms, 120000);
-    }
-
     #[test]
     fn build_send_body_slack() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
         let (method, body) = channel.build_send_body("C456", "hello", Some("1234567.890"));
         assert_eq!(method, "chat.postMessage");
         assert_eq!(body["channel"], "C456");
@@ -695,72 +497,95 @@ mod tests {
         assert_eq!(body["thread_ts"], "1234567.890");
     }
 
-    #[test]
-    fn parser_handle_is_shared_arc() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
-        // parser_handle should be an Arc — cloning should give a second reference
-        let handle_clone = Arc::clone(&channel.parser_handle);
-        // Both point to the same allocation
-        assert!(Arc::ptr_eq(&channel.parser_handle, &handle_clone));
+    #[tokio::test]
+    async fn start_processes_events() {
+        let (tx, rx) = mpsc::channel(64);
+        let channel =
+            RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx.clone(), rx);
+
+        let mut stream = channel.start().await.unwrap();
+
+        // Send an event
+        tx.send(ChannelEvent {
+            id: "1".into(),
+            event_type: "message".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: Some("alice".into()),
+            content: Some("hello".into()),
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();
+
+        use futures::StreamExt;
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .unwrap()
+            .unwrap();
+
+        assert_eq!(msg.content, "hello");
+        assert_eq!(msg.user_id, "U789");
     }
 
-    #[test]
-    fn with_max_failures_sets_value() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        )
-        .with_max_failures(10);
+    #[tokio::test]
+    async fn start_skips_non_message_events() {
+        let (tx, rx) = mpsc::channel(64);
+        let channel =
+            RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx.clone(), rx);
 
-        assert_eq!(channel.max_consecutive_failures, 10);
-    }
+        let mut stream = channel.start().await.unwrap();
 
-    #[test]
-    fn default_max_failures_is_50() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
-        assert_eq!(channel.max_consecutive_failures, 50);
-    }
+        // Send a non-message event (should be skipped)
+        tx.send(ChannelEvent {
+            id: "1".into(),
+            event_type: "reaction".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: None,
+            content: None,
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();
 
-    #[test]
-    fn empty_team_id_accepted_at_construction() {
-        // Regression: empty team_id (when no DB store is available) must not
-        // prevent channel construction or cause immediate shutdown.
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            String::new(), // empty team_id
-            "inst1".into(),
-            "user1".into(),
-        );
-        assert_eq!(channel.team_id, "");
-        // The reconnect loop now skips team validation when team_id is empty,
-        // so the channel remains alive.
+        // Send a real message
+        tx.send(ChannelEvent {
+            id: "2".into(),
+            event_type: "message".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: None,
+            content: Some("real message".into()),
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();
+
+        use futures::StreamExt;
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .unwrap()
+            .unwrap();
+
+        assert_eq!(msg.content, "real message");
     }
 
     #[tokio::test]
     async fn test_send_status_non_approval_is_noop() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
         let metadata = serde_json::json!({});
         let result = channel
             .send_status(
@@ -775,13 +600,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_send_status_approval_non_dm_skips() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
         let metadata = serde_json::json!({
             "event_type": "message",
             "channel_id": "C456",
@@ -794,6 +613,7 @@ mod tests {
                     tool_name: "shell".into(),
                     description: "run command".into(),
                     parameters: serde_json::json!({}),
+                    allow_always: true,
                 },
                 &metadata,
             )
@@ -804,13 +624,7 @@ mod tests {
 
     #[tokio::test]
     async fn test_send_status_approval_dm_missing_channel_id_errors() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
         let metadata = serde_json::json!({
             "event_type": "direct_message",
             "sender_id": "U789",
@@ -822,6 +636,7 @@ mod tests {
                     tool_name: "shell".into(),
                     description: "run command".into(),
                     parameters: serde_json::json!({}),
+                    allow_always: true,
                 },
                 &metadata,
             )
@@ -835,14 +650,8 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn test_send_status_approval_dm_missing_sender_id_errors() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+    async fn test_send_status_approval_dm_without_sender_id_is_ok() {
+        let channel = make_channel();
         let metadata = serde_json::json!({
             "event_type": "direct_message",
             "channel_id": "C456",
@@ -854,6 +663,7 @@ mod tests {
                     tool_name: "shell".into(),
                     description: "run command".into(),
                     parameters: serde_json::json!({}),
+                    allow_always: true,
                 },
                 &metadata,
             )
@@ -861,8 +671,8 @@ mod tests {
         assert!(result.is_err());
         let err = result.unwrap_err().to_string();
         assert!(
-            err.contains("sender_id"),
-            "expected sender_id error, got: {err}"
+            !err.contains("sender_id"),
+            "sender_id should not be required anymore, got: {err}"
         );
     }
 }

src/channels/relay/client.rs

@@ -1,15 +1,10 @@
 //! HTTP client for the channel-relay service.
 //!
 //! Wraps reqwest for all channel-relay API calls: OAuth initiation,
-//! SSE streaming, token renewal, and Slack API proxy.
+//! approvals, signing-secret fetch, and Slack API proxy.
 
-use std::pin::Pin;
-use std::task::{Context, Poll};
-
-use futures::Stream;
 use secrecy::{ExposeSecret, SecretString};
 use serde::{Deserialize, Serialize};
-use tokio::sync::mpsc;
 
 /// Known relay event types.
 pub mod event_types {
@@ -18,7 +13,7 @@ pub mod event_types {
     pub const MENTION: &str = "mention";
 }
 
-/// A parsed SSE event from the channel-relay stream.
+/// A parsed event from the channel-relay webhook callback.
 ///
 /// Field names match the channel-relay `ChannelEvent` struct exactly.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -123,21 +118,19 @@ impl RelayClient {
     ///
     /// Calls `GET /oauth/slack/auth` with `redirect(Policy::none())` and
     /// returns the `Location` header (Slack OAuth URL) without following it.
-    pub async fn initiate_oauth(
-        &self,
-        instance_id: &str,
-        user_id: &str,
-        callback_url: &str,
-    ) -> Result<String, RelayError> {
+    /// Initiate Slack OAuth. Channel-relay derives all URLs from the trusted
+    /// instance_url in chat-api. IronClaw only passes an optional CSRF nonce
+    /// for validating the callback — no URLs.
+    pub async fn initiate_oauth(&self, state_nonce: Option<&str>) -> Result<String, RelayError> {
+        let mut query: Vec<(&str, &str)> = vec![];
+        if let Some(nonce) = state_nonce {
+            query.push(("state_nonce", nonce));
+        }
         let resp = self
             .http
             .get(format!("{}/oauth/slack/auth", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
-            .query(&[
-                ("instance_id", instance_id),
-                ("user_id", user_id),
-                ("callback", callback_url),
-            ])
+            .bearer_auth(self.api_key.expose_secret())
+            .query(&query)
             .send()
             .await
             .map_err(|e| RelayError::Network(e.to_string()))?;
@@ -173,104 +166,69 @@ impl RelayClient {
         }
     }
 
-    /// Connect to the SSE event stream.
+    /// Register a pending approval and return the opaque approval token.
     ///
-    /// Returns a stream of parsed `ChannelEvent`s and the `JoinHandle` of the
-    /// background SSE parser task. The caller is responsible for reconnection
-    /// logic on stream end/error and for aborting the handle on shutdown.
-    pub async fn connect_stream(
+    /// Calls `POST /approvals` with the target team/channel/request identifiers.
+    /// The returned token is embedded in Slack button values instead of routing fields.
+    /// The relay derives the authorized approver from the connection's authed_user_id.
+    pub async fn create_approval(
         &self,
-        stream_token: &str,
-        stream_timeout_secs: u64,
-    ) -> Result<(ChannelEventStream, tokio::task::JoinHandle<()>), RelayError> {
-        let resp = self
-            .http
-            .get(format!("{}/stream", self.base_url))
-            .query(&[("token", stream_token)])
-            .timeout(std::time::Duration::from_secs(stream_timeout_secs))
-            .send()
-            .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
-
-        let status = resp.status();
-        if status == reqwest::StatusCode::UNAUTHORIZED {
-            return Err(RelayError::TokenExpired);
-        }
-        if !status.is_success() {
-            let body = resp.text().await.unwrap_or_default();
-            return Err(RelayError::Api {
-                status: status.as_u16(),
-                message: body,
-            });
-        }
-
-        // Spawn a background task that reads the SSE stream and sends parsed events
-        let (tx, rx) = mpsc::channel(64);
-        let byte_stream = resp.bytes_stream();
-        let handle = tokio::spawn(parse_sse_stream(byte_stream, tx));
-
-        Ok((ChannelEventStream { rx }, handle))
-    }
-
-    /// Renew an expired stream token.
-    ///
-    /// Calls `POST /stream/renew` with API key auth, returns a new stream token.
-    pub async fn renew_token(
-        &self,
-        instance_id: &str,
-        user_id: &str,
+        team_id: &str,
+        channel_id: &str,
+        thread_ts: Option<&str>,
+        request_id: &str,
     ) -> Result<String, RelayError> {
+        let mut body = serde_json::json!({
+            "team_id": team_id,
+            "channel_id": channel_id,
+            "request_id": request_id,
+        });
+        if let Some(ts) = thread_ts {
+            body["thread_ts"] = serde_json::Value::String(ts.to_string());
+        }
+
         let resp = self
             .http
-            .post(format!("{}/stream/renew", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
-            .json(&serde_json::json!({
-                "instance_id": instance_id,
-                "user_id": user_id,
-            }))
+            .post(format!("{}/approvals", self.base_url))
+            .bearer_auth(self.api_key.expose_secret())
+            .json(&body)
             .send()
             .await
             .map_err(|e| RelayError::Network(e.to_string()))?;
 
-        let status = resp.status();
-        if !status.is_success() {
+        if !resp.status().is_success() {
+            let status = resp.status().as_u16();
             let body = resp.text().await.unwrap_or_default();
             return Err(RelayError::Api {
-                status: status.as_u16(),
+                status,
                 message: body,
             });
         }
 
-        let body: serde_json::Value = resp
+        let result: serde_json::Value = resp
             .json()
             .await
             .map_err(|e| RelayError::Protocol(e.to_string()))?;
-        body.get("stream_token")
-            .or_else(|| body.get("token"))
+
+        result
+            .get("approval_token")
             .and_then(|v| v.as_str())
             .map(|s| s.to_string())
-            .ok_or_else(|| RelayError::Protocol("Response missing stream_token field".to_string()))
+            .ok_or_else(|| RelayError::Protocol("missing approval_token in response".to_string()))
     }
 
-    /// Proxy an API call through channel-relay for any provider.
-    ///
-    /// Calls `POST /proxy/{provider}/{method}?team_id=X&instance_id=Y` with the given JSON body.
     pub async fn proxy_provider(
         &self,
         provider: &str,
         team_id: &str,
         method: &str,
         body: serde_json::Value,
-        instance_id: Option<&str>,
     ) -> Result<serde_json::Value, RelayError> {
-        let mut query: Vec<(&str, &str)> = vec![("team_id", team_id)];
-        if let Some(iid) = instance_id {
-            query.push(("instance_id", iid));
-        }
+        let query: Vec<(&str, &str)> = vec![("team_id", team_id)];
         let resp = self
             .http
             .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
-            .header("X-API-Key", self.api_key.expose_secret())
+            .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .json(&body)
             .send()
@@ -291,12 +249,58 @@ impl RelayClient {
             .map_err(|e| RelayError::Protocol(e.to_string()))
     }
 
+    /// Fetch the per-instance callback signing secret from channel-relay.
+    ///
+    /// Calls `GET /relay/signing-secret` (authenticated) and returns the decoded
+    /// 32-byte secret. Called once at activation time; the result is cached in the
+    /// extension manager so subsequent calls to `relay_signing_secret()` use it.
+    pub async fn get_signing_secret(&self, team_id: &str) -> Result<Vec<u8>, RelayError> {
+        let resp = self
+            .http
+            .get(format!("{}/relay/signing-secret", self.base_url))
+            .bearer_auth(self.api_key.expose_secret())
+            .query(&[("team_id", team_id)])
+            .send()
+            .await
+            .map_err(|e| RelayError::Network(e.to_string()))?;
+
+        if !resp.status().is_success() {
+            let status = resp.status().as_u16();
+            let body = resp.text().await.unwrap_or_default();
+            return Err(RelayError::Api {
+                status,
+                message: body,
+            });
+        }
+
+        let body: serde_json::Value = resp
+            .json()
+            .await
+            .map_err(|e| RelayError::Protocol(e.to_string()))?;
+
+        body.get("signing_secret")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| RelayError::Protocol("missing signing_secret in response".to_string()))
+            .and_then(|raw| {
+                let decoded = hex::decode(raw).map_err(|e| {
+                    RelayError::Protocol(format!("invalid signing_secret hex: {e}"))
+                })?;
+                if decoded.len() != 32 {
+                    return Err(RelayError::Protocol(format!(
+                        "invalid signing_secret length: expected 32 bytes, got {}",
+                        decoded.len()
+                    )));
+                }
+                Ok(decoded)
+            })
+    }
+
     /// List active connections for an instance.
     pub async fn list_connections(&self, instance_id: &str) -> Result<Vec<Connection>, RelayError> {
         let resp = self
             .http
             .get(format!("{}/connections", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
+            .bearer_auth(self.api_key.expose_secret())
             .query(&[("instance_id", instance_id)])
             .send()
             .await
@@ -317,91 +321,6 @@ impl RelayClient {
     }
 }
 
-/// Async stream of parsed channel events from SSE.
-pub struct ChannelEventStream {
-    rx: mpsc::Receiver<ChannelEvent>,
-}
-
-impl Stream for ChannelEventStream {
-    type Item = ChannelEvent;
-
-    fn poll_next(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Option<Self::Item>> {
-        self.rx.poll_recv(cx)
-    }
-}
-
-/// Parse SSE format from a reqwest bytes stream.
-///
-/// SSE format:
-/// ```text
-/// event: message
-/// data: {"key": "value"}
-///
-/// ```
-/// Blank line terminates an event.
-async fn parse_sse_stream(
-    byte_stream: impl futures::Stream<Item = Result<bytes::Bytes, reqwest::Error>> + Send + 'static,
-    tx: mpsc::Sender<ChannelEvent>,
-) {
-    use futures::StreamExt;
-
-    let mut buffer = Vec::<u8>::new();
-    let mut event_type = String::new();
-    let mut data_lines = Vec::new();
-
-    let mut byte_stream = std::pin::pin!(byte_stream);
-    while let Some(chunk_result) = byte_stream.next().await {
-        let chunk = match chunk_result {
-            Ok(c) => c,
-            Err(e) => {
-                tracing::debug!(error = %e, "SSE stream chunk error");
-                break;
-            }
-        };
-
-        buffer.extend_from_slice(&chunk);
-
-        // Process complete lines (decode UTF-8 only on full lines to avoid
-        // corruption when multi-byte characters span chunk boundaries)
-        while let Some(newline_pos) = buffer.iter().position(|&b| b == b'\n') {
-            let line = String::from_utf8_lossy(&buffer[..newline_pos])
-                .trim_end_matches('\r')
-                .to_string();
-            buffer.drain(..=newline_pos);
-
-            if line.is_empty() {
-                // Blank line = end of event
-                if !data_lines.is_empty() {
-                    let data = data_lines.join("\n");
-                    if let Ok(mut event) = serde_json::from_str::<ChannelEvent>(&data) {
-                        if event.event_type.is_empty() && !event_type.is_empty() {
-                            event.event_type = event_type.clone();
-                        }
-                        if tx.send(event).await.is_err() {
-                            return; // receiver dropped
-                        }
-                    } else {
-                        tracing::debug!(
-                            event_type = %event_type,
-                            data_len = data.len(),
-                            "Failed to parse SSE event data as ChannelEvent"
-                        );
-                    }
-                }
-                event_type.clear();
-                data_lines.clear();
-            } else if let Some(value) = line.strip_prefix("event:") {
-                event_type = value.trim().to_string();
-            } else if let Some(value) = line.strip_prefix("data:") {
-                data_lines.push(value.trim().to_string());
-            }
-            // Ignore other fields (id:, retry:, comments)
-        }
-    }
-
-    tracing::debug!("SSE stream ended");
-}
-
 /// Errors from relay client operations.
 #[derive(Debug, thiserror::Error)]
 pub enum RelayError {
@@ -413,9 +332,6 @@ pub enum RelayError {
 
     #[error("Protocol error: {0}")]
     Protocol(String),
-
-    #[error("Stream token expired")]
-    TokenExpired,
 }
 
 #[cfg(test)]
@@ -494,9 +410,6 @@ mod tests {
             message: "unauthorized".into(),
         };
         assert_eq!(err.to_string(), "API error (HTTP 401): unauthorized");
-
-        let err = RelayError::TokenExpired;
-        assert_eq!(err.to_string(), "Stream token expired");
     }
 
     #[test]
@@ -518,32 +431,4 @@ mod tests {
         assert!(make(event_types::DIRECT_MESSAGE).is_message());
         assert!(make(event_types::MENTION).is_message());
     }
-
-    #[tokio::test]
-    async fn parse_sse_handles_multibyte_utf8_across_chunks() {
-        // The crab emoji (🦀) is 4 bytes: [0xF0, 0x9F, 0xA6, 0x80].
-        // Split it across two chunks to verify no U+FFFD corruption.
-        let event_json = r#"{"event_type":"message","content":"hello 🦀 world","provider_scope":"T1","channel_id":"C1","sender_id":"U1"}"#;
-        let full = format!("event: message\ndata: {}\n\n", event_json);
-        let bytes = full.as_bytes();
-
-        // Find the crab emoji and split mid-character
-        let crab_pos = bytes
-            .windows(4)
-            .position(|w| w == [0xF0, 0x9F, 0xA6, 0x80])
-            .expect("crab emoji not found");
-        let split_at = crab_pos + 2; // split in the middle of the 4-byte emoji
-
-        let chunk1 = bytes::Bytes::copy_from_slice(&bytes[..split_at]);
-        let chunk2 = bytes::Bytes::copy_from_slice(&bytes[split_at..]);
-
-        let chunks: Vec<Result<bytes::Bytes, reqwest::Error>> = vec![Ok(chunk1), Ok(chunk2)];
-        let stream = futures::stream::iter(chunks);
-
-        let (tx, mut rx) = mpsc::channel(8);
-        parse_sse_stream(stream, tx).await;
-
-        let event = rx.recv().await.expect("should receive event");
-        assert_eq!(event.text(), "hello 🦀 world");
-    }
 }

src/channels/relay/mod.rs

@@ -1,12 +1,13 @@
 //! Channel-relay integration for connecting to external messaging platforms
 //! (Slack) via the channel-relay service.
 //!
-//! The relay service handles OAuth, credential storage, webhook ingestion,
-//! and SSE event streaming. IronClaw consumes the SSE stream and sends
-//! messages via the relay's proxy API.
+//! The relay service handles OAuth, credential storage, and webhook ingestion.
+//! IronClaw receives events via webhook callbacks and sends messages via the
+//! relay's proxy API.
 
 pub mod channel;
 pub mod client;
+pub mod webhook;
 
 pub use channel::{DEFAULT_RELAY_NAME, RelayChannel};
 pub use client::RelayClient;

src/channels/relay/webhook.rs

@@ -0,0 +1,66 @@
+//! Shared relay webhook signature verification helpers.
+
+use hmac::{Hmac, Mac};
+use sha2::Sha256;
+
+type HmacSha256 = Hmac<Sha256>;
+
+/// Verify a relay callback HMAC signature.
+pub fn verify_relay_signature(
+    secret: &[u8],
+    timestamp: &str,
+    body: &[u8],
+    signature: &str,
+) -> bool {
+    verify_signature(secret, timestamp, body, signature)
+}
+
+fn verify_signature(secret: &[u8], timestamp: &str, body: &[u8], signature: &str) -> bool {
+    let mut mac = match HmacSha256::new_from_slice(secret) {
+        Ok(m) => m,
+        Err(_) => return false,
+    };
+    mac.update(timestamp.as_bytes());
+    mac.update(b".");
+    mac.update(body);
+    let expected = format!("sha256={}", hex::encode(mac.finalize().into_bytes()));
+    subtle::ConstantTimeEq::ct_eq(expected.as_bytes(), signature.as_bytes()).into()
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    fn make_signature(secret: &[u8], timestamp: &str, body: &[u8]) -> String {
+        let mut mac = HmacSha256::new_from_slice(secret).unwrap();
+        mac.update(timestamp.as_bytes());
+        mac.update(b".");
+        mac.update(body);
+        format!("sha256={}", hex::encode(mac.finalize().into_bytes()))
+    }
+
+    #[test]
+    fn verify_valid_signature() {
+        let secret = b"test-secret";
+        let body = b"hello";
+        let ts = "1234567890";
+        let sig = make_signature(secret, ts, body);
+        assert!(verify_signature(secret, ts, body, &sig));
+    }
+
+    #[test]
+    fn verify_wrong_secret_fails() {
+        let body = b"hello";
+        let ts = "1234567890";
+        let sig = make_signature(b"correct", ts, body);
+        assert!(!verify_signature(b"wrong", ts, body, &sig));
+    }
+
+    #[test]
+    fn verify_tampered_body_fails() {
+        let secret = b"secret";
+        let ts = "1234567890";
+        let sig = make_signature(secret, ts, b"original");
+        assert!(!verify_signature(secret, ts, b"tampered", &sig));
+    }
+}

src/channels/repl.rs

@@ -539,6 +539,7 @@ impl Channel for ReplChannel {
                 tool_name,
                 description,
                 parameters,
+                allow_always,
             } => {
                 let term_width = crossterm::terminal::size()
                     .map(|(w, _)| w as usize)
@@ -582,9 +583,13 @@ impl Channel for ReplChannel {
                 }
 
                 eprintln!("  \u{2502}");
-                eprintln!(
-                    "  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[34malways\x1b[0m (a) / \x1b[31mno\x1b[0m (n)"
-                );
+                if allow_always {
+                    eprintln!(
+                        "  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[34malways\x1b[0m (a) / \x1b[31mno\x1b[0m (n)"
+                    );
+                } else {
+                    eprintln!("  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[31mno\x1b[0m (n)");
+                }
                 eprintln!("  {bot_border}");
                 eprintln!();
             }

src/channels/signal.rs

@@ -915,20 +915,28 @@ impl Channel for SignalChannel {
             tool_name,
             description: _,
             parameters,
+            allow_always,
         } = &status
             && let Some(target_str) = metadata.get("signal_target").and_then(|v| v.as_str())
         {
             let params_json = serde_json::to_string_pretty(parameters).unwrap_or_default();
+            let always_line = if *allow_always {
+                format!(
+                    "\n• `always` or `a` - Approve and auto-approve future {} requests",
+                    tool_name
+                )
+            } else {
+                String::new()
+            };
             let message = format!(
                 "⚠️ *Approval Required*\n\n\
                  *Request ID:* `{}`\n\
                  *Tool:* {}\n\
                  *Parameters:*\n```\n{}\n```\n\n\
                  Reply with:\n\
-                 • `yes` or `y` - Approve this request\n\
-                 • `always` or `a` - Approve and auto-approve future {} requests\n\
+                 • `yes` or `y` - Approve this request{}\n\
                  • `no` or `n` - Deny",
-                request_id, tool_name, params_json, tool_name
+                request_id, tool_name, params_json, always_line
             );
             self.send_status_message(target_str, &message).await;
         }

src/channels/wasm/wrapper.rs

@@ -2043,6 +2043,7 @@ impl WasmChannel {
                 tool_name,
                 description,
                 parameters,
+                allow_always,
                 ..
             } => {
                 // WASM channels (Telegram, Slack, etc.) cannot render
@@ -2081,6 +2082,11 @@ impl WasmChannel {
                     })
                     .unwrap_or_default();
 
+                let reply_hint = if *allow_always {
+                    "Reply \"yes\" to approve, \"no\" to deny, or \"always\" to auto-approve."
+                } else {
+                    "Reply \"yes\" to approve or \"no\" to deny."
+                };
                 let prompt = format!(
                     "Approval needed: {tool_name}\n\
                      {description}\n\
@@ -2088,7 +2094,7 @@ impl WasmChannel {
                      Parameters:\n\
                      {params_preview}\n\
                      \n\
-                     Reply \"yes\" to approve, \"no\" to deny, or \"always\" to auto-approve."
+                     {reply_hint}"
                 );
 
                 let metadata_json = serde_json::to_string(metadata).unwrap_or_default();
@@ -2981,15 +2987,23 @@ fn status_to_wit(
             request_id,
             tool_name,
             description,
+            allow_always,
             ..
-        } => wit_channel::StatusUpdate {
-            status: wit_channel::StatusType::ApprovalNeeded,
-            message: format!(
-                "Approval needed for tool '{}'. {}\nRequest ID: {}\nReply with: yes (or /approve), no (or /deny), or always (or /always).",
-                tool_name, description, request_id
-            ),
-            metadata_json,
-        },
+        } => {
+            let reply_hint = if *allow_always {
+                "yes (or /approve), no (or /deny), or always (or /always)"
+            } else {
+                "yes (or /approve) or no (or /deny)"
+            };
+            wit_channel::StatusUpdate {
+                status: wit_channel::StatusType::ApprovalNeeded,
+                message: format!(
+                    "Approval needed for tool '{}'. {}\nRequest ID: {}\nReply with: {}.",
+                    tool_name, description, request_id, reply_hint
+                ),
+                metadata_json,
+            }
+        }
         StatusUpdate::JobStarted {
             job_id,
             title,
@@ -3670,6 +3684,7 @@ mod tests {
                     tool_name: "http_request".into(),
                     description: "Fetch weather".into(),
                     parameters: serde_json::json!({"url": "https://wttr.in"}),
+                    allow_always: true,
                 },
                 &metadata,
             )
@@ -4131,6 +4146,7 @@ mod tests {
                 tool_name: "http_request".to_string(),
                 description: "Fetch weather data".to_string(),
                 parameters: serde_json::json!({"url": "https://api.weather.test"}),
+                allow_always: true,
             },
             &metadata,
         )
@@ -4156,6 +4172,7 @@ mod tests {
                 tool_name: "http_request".to_string(),
                 description: "Fetch weather data".to_string(),
                 parameters: serde_json::json!({"url": "https://api.weather.test"}),
+                allow_always: true,
             },
             &metadata,
         )

src/channels/web/mod.rs

@@ -374,6 +374,7 @@ impl Channel for GatewayChannel {
                 tool_name,
                 description,
                 parameters,
+                allow_always,
             } => SseEvent::ApprovalNeeded {
                 request_id,
                 tool_name,
@@ -381,6 +382,7 @@ impl Channel for GatewayChannel {
                 parameters: serde_json::to_string_pretty(&parameters)
                     .unwrap_or_else(|_| parameters.to_string()),
                 thread_id,
+                allow_always,
             },
             StatusUpdate::AuthRequired {
                 extension_name,

src/channels/web/server.rs

@@ -19,6 +19,7 @@ use axum::{
     routing::{get, post},
 };
 use serde::Deserialize;
+use sha2::{Digest, Sha256};
 use tokio::sync::{mpsc, oneshot};
 use tokio_stream::StreamExt;
 use tower_http::cors::{AllowHeaders, CorsLayer};
@@ -63,6 +64,16 @@ pub type PromptQueue = Arc<
 pub type RoutineEngineSlot =
     Arc<tokio::sync::RwLock<Option<Arc<crate::agent::routine_engine::RoutineEngine>>>>;
 
+fn redact_oauth_state_for_logs(state: &str) -> String {
+    let digest = Sha256::digest(state.as_bytes());
+    let mut short_hash = String::with_capacity(12);
+    for byte in &digest[..6] {
+        use std::fmt::Write as _;
+        let _ = write!(&mut short_hash, "{byte:02x}");
+    }
+    format!("sha256:{short_hash}:len={}", state.len())
+}
+
 /// Simple sliding-window rate limiter.
 ///
 /// Tracks the number of requests in the current window. Resets when the window expires.
@@ -218,7 +229,8 @@ pub async fn start_server(
         .route(
             "/oauth/slack/callback",
             get(slack_relay_oauth_callback_handler),
-        );
+        )
+        .route("/relay/events", post(relay_events_handler));
 
     // Protected routes (require auth)
     let auth_state = AuthState { token: auth_token };
@@ -565,22 +577,35 @@ async fn oauth_callback_handler(
         }
     };
 
-    // Strip instance prefix from state for registry lookup.
-    // Platform nginx sends `state=instance:nonce` but flows are keyed by nonce only.
-    let lookup_key = oauth_defaults::strip_instance_prefix(&state_param);
+    let decoded_state = match oauth_defaults::decode_hosted_oauth_state(&state_param) {
+        Ok(decoded) => decoded,
+        Err(error) => {
+            let redacted_state = redact_oauth_state_for_logs(&state_param);
+            tracing::warn!(
+                state = %redacted_state,
+                error = %error,
+                "OAuth callback received with malformed state"
+            );
+            clear_auth_mode(&state).await;
+            return oauth_error_page("IronClaw");
+        }
+    };
+    let lookup_key = decoded_state.flow_id.clone();
 
     let flow = ext_mgr
         .pending_oauth_flows()
         .write()
         .await
-        .remove(lookup_key);
+        .remove(&lookup_key);
 
     let flow = match flow {
         Some(f) => f,
         None => {
+            let redacted_state = redact_oauth_state_for_logs(&state_param);
+            let redacted_lookup_key = redact_oauth_state_for_logs(&lookup_key);
             tracing::warn!(
-                state = %state_param,
-                lookup_key = %lookup_key,
+                state = %redacted_state,
+                lookup_key = %redacted_lookup_key,
                 "OAuth callback received with unknown or expired state"
             );
             clear_auth_mode(&state).await;
@@ -607,33 +632,29 @@ async fn oauth_callback_handler(
     }
 
     // Exchange the authorization code for tokens.
-    // Use the platform exchange proxy when configured (keeps client_secret off container),
-    // otherwise call the provider's token URL directly.
-    let exchange_proxy_url = std::env::var("IRONCLAW_OAUTH_EXCHANGE_URL").ok();
+    // Use the platform exchange proxy when configured, otherwise call the
+    // provider's token URL directly.
+    let exchange_proxy_url = oauth_defaults::exchange_proxy_url();
 
     let result: Result<(), String> = async {
-        let token_response = if let (Some(proxy_url), None) = (&exchange_proxy_url, &flow.resource)
-        {
-            // Use the platform exchange proxy when configured and no resource
-            // parameter is needed. The proxy holds client_secret server-side so
-            // the container never sees it. MCP flows (resource.is_some()) bypass
-            // the proxy because it doesn't forward the RFC 8707 resource param.
+        let token_response = if let Some(proxy_url) = &exchange_proxy_url {
             let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
-            oauth_defaults::exchange_via_proxy(
+            oauth_defaults::exchange_via_proxy(oauth_defaults::ProxyTokenExchangeRequest {
                 proxy_url,
                 gateway_token,
-                &code,
-                &flow.redirect_uri,
-                flow.code_verifier.as_deref(),
-                &flow.access_token_field,
-            )
+                token_url: &flow.token_url,
+                client_id: &flow.client_id,
+                client_secret: flow.client_secret.as_deref(),
+                code: &code,
+                redirect_uri: &flow.redirect_uri,
+                code_verifier: flow.code_verifier.as_deref(),
+                access_token_field: &flow.access_token_field,
+                extra_token_params: &flow.token_exchange_extra_params,
+            })
             .await
             .map_err(|e| e.to_string())?
         } else {
-            // Direct token exchange: uses exchange_oauth_code_with_resource so MCP
-            // flows can include the RFC 8707 `resource` parameter to scope the
-            // issued token to the specific MCP server.
-            oauth_defaults::exchange_oauth_code_with_resource(
+            oauth_defaults::exchange_oauth_code_with_params(
                 &flow.token_url,
                 &flow.client_id,
                 flow.client_secret.as_deref(),
@@ -641,7 +662,7 @@ async fn oauth_callback_handler(
                 &flow.redirect_uri,
                 flow.code_verifier.as_deref(),
                 &flow.access_token_field,
-                flow.resource.as_deref(),
+                &flow.token_exchange_extra_params,
             )
             .await
             .map_err(|e| e.to_string())?
@@ -668,10 +689,8 @@ async fn oauth_callback_handler(
         .await
         .map_err(|e| e.to_string())?;
 
-        // For MCP OAuth flows (identified by resource field), persist the
-        // client_id so token refresh works without re-authentication.
-        // The CLI flow stores this in authorize_mcp_server(); the gateway
-        // callback must do the same.
+        // Persist the client_id for flows that need it after the session ends
+        // (for example DCR-based MCP refresh).
         if let Some(ref client_id_secret) = flow.client_id_secret_name {
             let params = crate::secrets::CreateSecretParams::new(client_id_secret, &flow.client_id)
                 .with_provider(flow.provider.as_ref().cloned().unwrap_or_default());
@@ -752,11 +771,103 @@ async fn oauth_callback_handler(
     axum::response::Html(html).into_response()
 }
 
+/// Webhook endpoint for receiving relay events from channel-relay.
+///
+/// PUBLIC route — authenticated via HMAC signature (X-Relay-Signature header).
+async fn relay_events_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    body: axum::body::Bytes,
+) -> impl IntoResponse {
+    let ext_mgr = match state.extension_manager.as_ref() {
+        Some(mgr) => mgr,
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "not ready").into_response();
+        }
+    };
+
+    let signing_secret = match ext_mgr.relay_signing_secret() {
+        Some(s) => s,
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "relay not configured").into_response();
+        }
+    };
+
+    // Verify signature
+    let signature = match headers
+        .get("x-relay-signature")
+        .and_then(|v| v.to_str().ok())
+    {
+        Some(s) => s.to_string(),
+        None => {
+            return (StatusCode::UNAUTHORIZED, "missing signature").into_response();
+        }
+    };
+
+    let timestamp = match headers
+        .get("x-relay-timestamp")
+        .and_then(|v| v.to_str().ok())
+    {
+        Some(t) => t.to_string(),
+        None => {
+            return (StatusCode::UNAUTHORIZED, "missing timestamp").into_response();
+        }
+    };
+
+    // Check timestamp freshness (5 min window)
+    let ts: i64 = match timestamp.parse() {
+        Ok(t) => t,
+        Err(_) => {
+            return (StatusCode::BAD_REQUEST, "malformed timestamp").into_response();
+        }
+    };
+    let now = chrono::Utc::now().timestamp();
+    if (now - ts).abs() > 300 {
+        return (StatusCode::UNAUTHORIZED, "stale timestamp").into_response();
+    }
+
+    // Verify HMAC: sha256(secret, timestamp + "." + body)
+    if !crate::channels::relay::webhook::verify_relay_signature(
+        &signing_secret,
+        &timestamp,
+        &body,
+        &signature,
+    ) {
+        return (StatusCode::UNAUTHORIZED, "invalid signature").into_response();
+    }
+
+    // Parse event
+    let event: crate::channels::relay::client::ChannelEvent = match serde_json::from_slice(&body) {
+        Ok(e) => e,
+        Err(e) => {
+            tracing::warn!(error = %e, "relay callback invalid JSON");
+            return (StatusCode::BAD_REQUEST, "invalid JSON").into_response();
+        }
+    };
+
+    // Push to relay channel
+    let event_tx_guard = ext_mgr.relay_event_tx();
+    let event_tx = event_tx_guard.lock().await;
+    match event_tx.as_ref() {
+        Some(tx) => {
+            if let Err(e) = tx.try_send(event) {
+                tracing::warn!(error = %e, "relay event channel full or closed");
+                return (StatusCode::SERVICE_UNAVAILABLE, "event queue full").into_response();
+            }
+        }
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "relay channel not active").into_response();
+        }
+    }
+
+    Json(serde_json::json!({"ok": true})).into_response()
+}
+
 /// OAuth callback for Slack via channel-relay.
 ///
 /// This is a PUBLIC route (no Bearer token required) because channel-relay
 /// redirects the user's browser here after Slack OAuth completes.
-/// Query params: `stream_token`, `provider`, `team_id`.
+/// Query params: `provider`, `team_id`.
 async fn slack_relay_oauth_callback_handler(
     State(state): State<Arc<GatewayState>>,
     Query(params): Query<std::collections::HashMap<String, String>>,
@@ -773,27 +884,6 @@ async fn slack_relay_oauth_callback_handler(
         .into_response();
     }
 
-    // Validate stream_token: required, non-empty, max 2048 bytes
-    let stream_token = match params.get("stream_token") {
-        Some(t) if !t.is_empty() && t.len() <= 2048 => t.clone(),
-        Some(t) if t.len() > 2048 => {
-            return axum::response::Html(
-                "<html><body style='font-family: system-ui; text-align: center; padding: 60px;'>\
-                 <h2>Error</h2><p>Invalid callback parameters.</p></body></html>"
-                    .to_string(),
-            )
-            .into_response();
-        }
-        _ => {
-            return axum::response::Html(
-                "<html><body style='font-family: system-ui; text-align: center; padding: 60px;'>\
-                 <h2>Error</h2><p>Invalid callback parameters.</p></body></html>"
-                    .to_string(),
-            )
-            .into_response();
-        }
-    };
-
     // Validate team_id format: empty or T followed by alphanumeric (max 20 chars)
     let team_id = params.get("team_id").cloned().unwrap_or_default();
     if !team_id.is_empty() {
@@ -879,30 +969,16 @@ async fn slack_relay_oauth_callback_handler(
     let _ = ext_mgr.secrets().delete(&state.user_id, &state_key).await;
 
     let result: Result<(), String> = async {
-        // Store the stream token as a secret
-        let token_key = format!("relay:{}:stream_token", DEFAULT_RELAY_NAME);
-        let _ = ext_mgr.secrets().delete(&state.user_id, &token_key).await;
-        ext_mgr
-            .secrets()
-            .create(
-                &state.user_id,
-                crate::secrets::CreateSecretParams {
-                    name: token_key,
-                    value: secrecy::SecretString::from(stream_token),
-                    provider: Some(provider.clone()),
-                    expires_at: None,
-                },
-            )
-            .await
-            .map_err(|e| format!("Failed to store stream token: {}", e))?;
+        let store = state.store.as_ref().ok_or_else(|| {
+            "Relay activation requires persistent settings storage; no-db mode is unsupported."
+                .to_string()
+        })?;
 
         // Store team_id in settings
-        if let Some(ref store) = state.store {
-            let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-            let _ = store
-                .set_setting(&state.user_id, &team_id_key, &serde_json::json!(team_id))
-                .await;
-        }
+        let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
+        let _ = store
+            .set_setting(&state.user_id, &team_id_key, &serde_json::json!(team_id))
+            .await;
 
         // Activate the relay channel
         ext_mgr
@@ -3253,7 +3329,7 @@ mod tests {
             secrets,
             sse_sender: None,
             gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
             client_id_secret_name: None,
             created_at,
         };
@@ -3321,7 +3397,7 @@ mod tests {
             secrets,
             sse_sender: Some(sender),
             gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
             client_id_secret_name: None,
             created_at,
         };
@@ -3424,7 +3500,7 @@ mod tests {
             secrets,
             sse_sender: None,
             gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
             client_id_secret_name: None,
             // Expired — handler will reject after lookup (no network I/O)
             created_at,
@@ -3476,6 +3552,85 @@ mod tests {
         );
     }
 
+    #[tokio::test]
+    async fn test_oauth_callback_accepts_versioned_hosted_state() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync> =
+            Arc::new(crate::secrets::InMemorySecretsStore::new(Arc::new(
+                crate::secrets::SecretsCrypto::new(secrecy::SecretString::from(
+                    TEST_GATEWAY_CRYPTO_KEY.to_string(),
+                ))
+                .expect("crypto"),
+            )));
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(secrets.clone());
+
+        let Some(created_at) = expired_flow_created_at() else {
+            eprintln!("Skipping versioned OAuth state test: monotonic uptime below expiry window");
+            return;
+        };
+        let flow = crate::cli::oauth_defaults::PendingOAuthFlow {
+            extension_name: "test_tool".to_string(),
+            display_name: "Test Tool".to_string(),
+            token_url: "https://example.com/token".to_string(),
+            client_id: "client123".to_string(),
+            client_secret: None,
+            redirect_uri: "https://example.com/oauth/callback".to_string(),
+            code_verifier: None,
+            access_token_field: "access_token".to_string(),
+            secret_name: "test_token".to_string(),
+            provider: None,
+            validation_endpoint: None,
+            scopes: vec![],
+            user_id: "test".to_string(),
+            secrets,
+            sse_sender: None,
+            gateway_token: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
+            client_id_secret_name: None,
+            created_at,
+        };
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("test_nonce".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr.clone()));
+        let app = test_oauth_router(state);
+        let versioned_state =
+            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", Some("myinstance"));
+
+        let req = axum::http::Request::builder()
+            .uri(format!(
+                "/oauth/callback?code=fake_code&state={}",
+                urlencoding::encode(&versioned_state)
+            ))
+            .body(Body::empty())
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let html = String::from_utf8_lossy(&body);
+        assert!(html.contains("Authorization Failed"));
+        assert!(
+            ext_mgr
+                .pending_oauth_flows()
+                .read()
+                .await
+                .get("test_nonce")
+                .is_none()
+        );
+    }
+
     // --- Slack relay OAuth CSRF tests ---
 
     fn test_relay_oauth_router(state: Arc<GatewayState>) -> Router {
@@ -3533,7 +3688,7 @@ mod tests {
 
         // Callback without state param should be rejected
         let req = axum::http::Request::builder()
-            .uri("/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack")
+            .uri("/oauth/slack/callback?team_id=T123&provider=slack")
             .body(Body::empty())
             .expect("request");
 
@@ -3577,7 +3732,7 @@ mod tests {
 
         // Callback with wrong state param
         let req = axum::http::Request::builder()
-            .uri("/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack&state=wrong-nonce")
+            .uri("/oauth/slack/callback?team_id=T123&provider=slack&state=wrong-nonce")
             .body(Body::empty())
             .expect("request");
 
@@ -3625,7 +3780,7 @@ mod tests {
         // we just verify it doesn't return a CSRF error.
         let req = axum::http::Request::builder()
             .uri(format!(
-                "/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack&state={}",
+                "/oauth/slack/callback?team_id=T123&provider=slack&state={}",
                 nonce
             ))
             .body(Body::empty())

src/channels/web/static/app.js

@@ -1138,18 +1138,19 @@ function showApproval(data) {
   approveBtn.textContent = I18n.t('approval.approve');
   approveBtn.addEventListener('click', () => sendApprovalAction(data.request_id, 'approve'));
 
-  const alwaysBtn = document.createElement('button');
-  alwaysBtn.className = 'always';
-  alwaysBtn.textContent = I18n.t('approval.always');
-  alwaysBtn.addEventListener('click', () => sendApprovalAction(data.request_id, 'always'));
-
   const denyBtn = document.createElement('button');
   denyBtn.className = 'deny';
   denyBtn.textContent = I18n.t('approval.deny');
   denyBtn.addEventListener('click', () => sendApprovalAction(data.request_id, 'deny'));
 
   actions.appendChild(approveBtn);
-  actions.appendChild(alwaysBtn);
+  if (data.allow_always !== false) {
+    const alwaysBtn = document.createElement('button');
+    alwaysBtn.className = 'always';
+    alwaysBtn.textContent = I18n.t('approval.always');
+    alwaysBtn.addEventListener('click', () => sendApprovalAction(data.request_id, 'always'));
+    actions.appendChild(alwaysBtn);
+  }
   actions.appendChild(denyBtn);
   card.appendChild(actions);
 

src/channels/web/types.rs

@@ -177,6 +177,8 @@ pub enum SseEvent {
         parameters: String,
         #[serde(skip_serializing_if = "Option::is_none")]
         thread_id: Option<String>,
+        /// Whether the "always" auto-approve option should be shown.
+        allow_always: bool,
     },
     #[serde(rename = "auth_required")]
     AuthRequired {
@@ -230,6 +232,8 @@ pub enum SseEvent {
         status: String,
         #[serde(skip_serializing_if = "Option::is_none")]
         session_id: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        fallback_deliverable: Option<serde_json::Value>,
     },
 
     /// An image was generated by a tool.
@@ -1080,6 +1084,7 @@ mod tests {
             description: "Run ls".to_string(),
             parameters: "{}".to_string(),
             thread_id: Some("t1".to_string()),
+            allow_always: true,
         };
         let ws = WsServerMessage::from_sse_event(&sse);
         match ws {

src/cli/memory.rs

@@ -7,17 +7,18 @@ use std::sync::Arc;
 
 use clap::Subcommand;
 
-use crate::workspace::{EmbeddingProvider, SearchConfig, Workspace};
+use crate::workspace::{EmbeddingCacheConfig, EmbeddingProvider, SearchConfig, Workspace};
 
 /// Run a memory command using the Database trait (works with any backend).
 pub async fn run_memory_command_with_db(
     cmd: MemoryCommand,
     db: std::sync::Arc<dyn crate::db::Database>,
     embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    cache_config: EmbeddingCacheConfig,
 ) -> anyhow::Result<()> {
     let mut workspace = Workspace::new_with_db("default", db);
     if let Some(emb) = embeddings {
-        workspace = workspace.with_embeddings(emb);
+        workspace = workspace.with_embeddings_cached(emb, cache_config);
     }
 
     match cmd {
@@ -85,10 +86,11 @@ pub async fn run_memory_command(
     cmd: MemoryCommand,
     pool: deadpool_postgres::Pool,
     embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    cache_config: EmbeddingCacheConfig,
 ) -> anyhow::Result<()> {
     let mut workspace = Workspace::new("default", pool);
     if let Some(emb) = embeddings {
-        workspace = workspace.with_embeddings(emb);
+        workspace = workspace.with_embeddings_cached(emb, cache_config);
     }
 
     match cmd {

src/cli/mod.rs

@@ -336,7 +336,10 @@ pub async fn run_memory_command(mem_cmd: &MemoryCommand) -> anyhow::Result<()> {
         .await
         .map_err(|e| anyhow::anyhow!("{}", e))?;
 
-    run_memory_command_with_db(mem_cmd.clone(), db, embeddings).await
+    let cache_config = crate::workspace::EmbeddingCacheConfig {
+        max_entries: config.embeddings.cache_size,
+    };
+    run_memory_command_with_db(mem_cmd.clone(), db, embeddings, cache_config).await
 }
 
 #[cfg(test)]

src/cli/oauth_defaults.rs

@@ -5,17 +5,10 @@
 //!
 //! # Built-in Credentials
 //!
-//! Many CLI tools (gcloud, rclone, gdrive) ship with default OAuth credentials
-//! so users don't need to register their own OAuth app. Google explicitly
-//! documents that client_secret for "Desktop App" / "Installed App" types
-//! is NOT actually secret.
-//!
-//! Default credentials are hardcoded below. They can be overridden at:
-//!
-//! - **Compile time**: Set IRONCLAW_GOOGLE_CLIENT_ID / IRONCLAW_GOOGLE_CLIENT_SECRET
-//!   env vars before building to replace the hardcoded defaults.
-//! - **Runtime**: Users can set GOOGLE_OAUTH_CLIENT_ID / GOOGLE_OAUTH_CLIENT_SECRET
-//!   env vars, which take priority over built-in defaults.
+//! Some providers ship with built-in OAuth credentials so users don't need to
+//! register their own OAuth app just to get started. Today this module only
+//! includes built-in defaults for Google-family tools, and those defaults can
+//! be overridden by provider-specific environment variables when needed.
 
 use std::collections::HashMap;
 use std::sync::Arc;
@@ -23,6 +16,7 @@ use std::time::Duration;
 
 use base64::{Engine, engine::general_purpose::URL_SAFE_NO_PAD};
 use rand::RngCore;
+use serde::{Deserialize, Serialize};
 use sha2::{Digest, Sha256};
 use tokio::sync::RwLock;
 
@@ -60,6 +54,14 @@ pub fn builtin_credentials(secret_name: &str) -> Option<OAuthCredentials> {
     }
 }
 
+/// Returns the compile-time override env var name, if this provider supports one.
+pub fn builtin_client_id_override_env(secret_name: &str) -> Option<&'static str> {
+    match secret_name {
+        "google_oauth_token" => Some("IRONCLAW_GOOGLE_CLIENT_ID"),
+        _ => None,
+    }
+}
+
 // ── Shared callback server ──────────────────────────────────────────────
 
 // Core OAuth callback infrastructure is defined in `crate::llm::oauth_helpers`
@@ -173,9 +175,8 @@ pub async fn exchange_oauth_code(
     code_verifier: Option<&str>,
     access_token_field: &str,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
-    // Delegates to exchange_oauth_code_with_resource with resource=None.
-    // Non-MCP OAuth flows don't need the RFC 8707 resource parameter.
-    exchange_oauth_code_with_resource(
+    let extra_token_params = HashMap::new();
+    exchange_oauth_code_with_params(
         token_url,
         client_id,
         client_secret,
@@ -183,16 +184,14 @@ pub async fn exchange_oauth_code(
         redirect_uri,
         code_verifier,
         access_token_field,
-        None,
+        &extra_token_params,
     )
     .await
 }
 
-/// Exchange an OAuth authorization code for tokens, with optional RFC 8707 `resource` parameter.
-///
-/// The `resource` parameter scopes the issued token to a specific server (used by MCP OAuth).
+/// Exchange an OAuth authorization code for tokens with generic extra form parameters.
 #[allow(clippy::too_many_arguments)]
-pub async fn exchange_oauth_code_with_resource(
+pub async fn exchange_oauth_code_with_params(
     token_url: &str,
     client_id: &str,
     client_secret: Option<&str>,
@@ -200,7 +199,7 @@ pub async fn exchange_oauth_code_with_resource(
     redirect_uri: &str,
     code_verifier: Option<&str>,
     access_token_field: &str,
-    resource: Option<&str>,
+    extra_token_params: &HashMap<String, String>,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
     let client = reqwest::Client::new();
     let mut token_params = vec![
@@ -213,10 +212,8 @@ pub async fn exchange_oauth_code_with_resource(
         token_params.push(("code_verifier", verifier.to_string()));
     }
 
-    // RFC 8707: include the `resource` parameter so the authorization server
-    // scopes the issued token to the specific MCP server (protected resource).
-    if let Some(resource) = resource {
-        token_params.push(("resource", resource.to_string()));
+    for (key, value) in extra_token_params {
+        token_params.push((key.as_str(), value.clone()));
     }
 
     let mut request = client.post(token_url);
@@ -276,6 +273,37 @@ pub async fn exchange_oauth_code_with_resource(
     })
 }
 
+/// Exchange an OAuth authorization code for tokens, with optional RFC 8707 `resource` parameter.
+///
+/// The `resource` parameter scopes the issued token to a specific server (used by MCP OAuth).
+#[allow(clippy::too_many_arguments)]
+pub async fn exchange_oauth_code_with_resource(
+    token_url: &str,
+    client_id: &str,
+    client_secret: Option<&str>,
+    code: &str,
+    redirect_uri: &str,
+    code_verifier: Option<&str>,
+    access_token_field: &str,
+    resource: Option<&str>,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    let mut extra_token_params = HashMap::new();
+    if let Some(resource) = resource {
+        extra_token_params.insert("resource".to_string(), resource.to_string());
+    }
+    exchange_oauth_code_with_params(
+        token_url,
+        client_id,
+        client_secret,
+        code,
+        redirect_uri,
+        code_verifier,
+        access_token_field,
+        &extra_token_params,
+    )
+    .await
+}
+
 /// Store OAuth tokens (access + refresh) in the secrets store.
 ///
 /// Also stores the granted scopes as `{secret_name}_scopes` so that scope
@@ -423,9 +451,9 @@ pub struct PendingOAuthFlow {
     pub sse_sender: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
     /// Gateway auth token for authenticating with the platform token exchange proxy.
     pub gateway_token: Option<String>,
-    /// RFC 8707 resource parameter (MCP OAuth only).
-    /// Sent during token exchange to scope the token to a specific MCP server.
-    pub resource: Option<String>,
+    /// Additional form params for the token exchange request.
+    /// Used for provider-specific requirements such as RFC 8707 `resource`.
+    pub token_exchange_extra_params: HashMap<String, String>,
     /// Secret name for persisting the client ID (MCP OAuth only).
     /// Needed so token refresh can find the client_id after the session ends.
     pub client_id_secret_name: Option<String>,
@@ -459,9 +487,7 @@ pub fn new_pending_oauth_registry() -> PendingOAuthRegistry {
 /// URL, meaning the user's browser will redirect to a hosted gateway rather than
 /// localhost.
 pub fn use_gateway_callback() -> bool {
-    std::env::var("IRONCLAW_OAUTH_CALLBACK_URL")
-        .ok()
-        .filter(|v| !v.is_empty())
+    crate::config::helpers::env_or_override("IRONCLAW_OAUTH_CALLBACK_URL")
         .map(|raw| {
             url::Url::parse(&raw)
                 .ok()
@@ -472,6 +498,13 @@ pub fn use_gateway_callback() -> bool {
         .unwrap_or(false)
 }
 
+/// Returns the configured OAuth token-exchange proxy URL, if any.
+pub fn exchange_proxy_url() -> Option<String> {
+    crate::config::helpers::env_or_override("IRONCLAW_OAUTH_EXCHANGE_URL")
+        .map(|url| url.trim().to_string())
+        .filter(|url| !url.is_empty())
+}
+
 /// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
 pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);
 
@@ -486,23 +519,117 @@ pub async fn sweep_expired_flows(registry: &PendingOAuthRegistry) {
 
 // ── Platform routing helpers ────────────────────────────────────────
 
-/// Prepend instance name to CSRF state for platform routing.
+const HOSTED_STATE_PREFIX: &str = "ic2";
+const HOSTED_STATE_CHECKSUM_BYTES: usize = 12;
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct DecodedHostedOAuthState {
+    pub flow_id: String,
+    pub instance_name: Option<String>,
+    pub is_legacy: bool,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+struct HostedOAuthStatePayload {
+    flow_id: String,
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    instance_name: Option<String>,
+    issued_at: u64,
+}
+
+fn current_instance_name() -> Option<String> {
+    crate::config::helpers::env_or_override("IRONCLAW_INSTANCE_NAME")
+        .or_else(|| crate::config::helpers::env_or_override("OPENCLAW_INSTANCE_NAME"))
+        .filter(|v| !v.is_empty())
+}
+
+fn hosted_state_checksum(payload_bytes: &[u8]) -> String {
+    let digest = Sha256::digest(payload_bytes);
+    URL_SAFE_NO_PAD.encode(&digest[..HOSTED_STATE_CHECKSUM_BYTES])
+}
+
+/// Build a versioned hosted OAuth state envelope.
 ///
-/// The NEAR AI platform nginx proxy at `auth.DOMAIN` parses the instance name
-/// from the `state` query parameter (format: `instance:nonce`) to route the
-/// OAuth callback to the correct container.
-///
-/// Returns the nonce unchanged when `IRONCLAW_INSTANCE_NAME` is not set
-/// (local/non-platform mode).
-pub fn build_platform_state(nonce: &str) -> String {
-    let instance = std::env::var("IRONCLAW_INSTANCE_NAME")
-        .or_else(|_| std::env::var("OPENCLAW_INSTANCE_NAME"))
-        .ok()
-        .filter(|v| !v.is_empty());
-    match instance {
-        Some(name) => format!("{}:{}", name, nonce),
-        None => nonce.to_string(),
+/// The encoded value is opaque to providers and can be decoded by both
+/// IronClaw and the external auth proxy for routing and callback lookup.
+pub fn encode_hosted_oauth_state(flow_id: &str, instance_name: Option<&str>) -> String {
+    let payload = HostedOAuthStatePayload {
+        flow_id: flow_id.to_string(),
+        instance_name: instance_name
+            .map(str::trim)
+            .filter(|v| !v.is_empty())
+            .map(str::to_string),
+        issued_at: std::time::SystemTime::now()
+            .duration_since(std::time::UNIX_EPOCH)
+            .unwrap_or_default()
+            .as_secs(),
+    };
+    let payload_json = match serde_json::to_vec(&payload) {
+        Ok(payload_json) => payload_json,
+        Err(error) => {
+            tracing::warn!(%error, flow_id, "Failed to serialize hosted OAuth state payload");
+            return payload.flow_id;
+        }
+    };
+    let payload = URL_SAFE_NO_PAD.encode(&payload_json);
+    let checksum = hosted_state_checksum(&payload_json);
+    format!("{HOSTED_STATE_PREFIX}.{payload}.{checksum}")
+}
+
+/// Decode hosted OAuth state in either the new versioned format or the
+/// legacy `instance:nonce`/`nonce` forms.
+pub fn decode_hosted_oauth_state(state: &str) -> Result<DecodedHostedOAuthState, String> {
+    if let Some(rest) = state.strip_prefix(&format!("{HOSTED_STATE_PREFIX}."))
+        && let Some((payload_b64, checksum)) = rest.rsplit_once('.')
+        && let Ok(payload_json) = URL_SAFE_NO_PAD.decode(payload_b64)
+    {
+        let expected_checksum = hosted_state_checksum(&payload_json);
+        if checksum != expected_checksum {
+            return Err("Hosted OAuth state checksum mismatch".to_string());
+        }
+        if let Ok(payload) = serde_json::from_slice::<HostedOAuthStatePayload>(&payload_json)
+            && !payload.flow_id.trim().is_empty()
+        {
+            return Ok(DecodedHostedOAuthState {
+                flow_id: payload.flow_id,
+                instance_name: payload.instance_name.filter(|v| !v.is_empty()),
+                is_legacy: false,
+            });
+        }
     }
+
+    if let Some((instance_name, flow_id)) = state.split_once(':') {
+        if flow_id.is_empty() {
+            return Err("Hosted OAuth legacy state is missing flow_id".to_string());
+        }
+        return Ok(DecodedHostedOAuthState {
+            flow_id: flow_id.to_string(),
+            instance_name: if instance_name.is_empty() {
+                None
+            } else {
+                Some(instance_name.to_string())
+            },
+            is_legacy: true,
+        });
+    }
+
+    if state.is_empty() {
+        return Err("Hosted OAuth state is empty".to_string());
+    }
+
+    Ok(DecodedHostedOAuthState {
+        flow_id: state.to_string(),
+        instance_name: None,
+        is_legacy: true,
+    })
+}
+
+/// Build the hosted callback state used by the public OAuth callback endpoint.
+///
+/// New flows emit a versioned opaque envelope, while callback decoding accepts
+/// both the envelope and the legacy `instance:nonce` contract.
+pub fn build_platform_state(nonce: &str) -> String {
+    encode_hosted_oauth_state(nonce, current_instance_name().as_deref())
 }
 
 /// Strip the instance prefix from a state parameter to recover the lookup nonce.
@@ -517,43 +644,62 @@ pub fn strip_instance_prefix(state: &str) -> &str {
         .unwrap_or(state)
 }
 
+pub struct ProxyTokenExchangeRequest<'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 code: &'a str,
+    pub redirect_uri: &'a str,
+    pub code_verifier: Option<&'a str>,
+    pub access_token_field: &'a str,
+    pub extra_token_params: &'a HashMap<String, String>,
+}
+
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
-/// The proxy holds `client_secret` server-side so the container never sees it.
-/// Authenticated via the gateway auth token (Bearer header).
+/// 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.
 ///
-/// The proxy expects form params `{code, redirect_uri, code_verifier}` and
-/// returns a standard Google token response `{access_token, refresh_token, expires_in}`.
+/// The proxy expects standard OAuth form params plus optional provider-specific
+/// token params and returns a standard token response such as
+/// `{access_token, refresh_token, expires_in}`.
 pub async fn exchange_via_proxy(
-    proxy_url: &str,
-    gateway_token: &str,
-    code: &str,
-    redirect_uri: &str,
-    code_verifier: Option<&str>,
-    access_token_field: &str,
+    request: ProxyTokenExchangeRequest<'_>,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
-    if gateway_token.is_empty() {
+    if request.gateway_token.is_empty() {
         return Err(OAuthCallbackError::Io(
             "Gateway auth token is required for proxy token exchange".to_string(),
         ));
     }
-    let exchange_url = format!("{}/oauth/exchange", proxy_url.trim_end_matches('/'));
+    let exchange_url = format!("{}/oauth/exchange", request.proxy_url.trim_end_matches('/'));
 
     let client = reqwest::Client::builder()
         .timeout(Duration::from_secs(60))
         .build()
         .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
     let mut params = vec![
-        ("code", code.to_string()),
-        ("redirect_uri", redirect_uri.to_string()),
+        ("code", request.code.to_string()),
+        ("redirect_uri", request.redirect_uri.to_string()),
+        ("token_url", request.token_url.to_string()),
+        ("client_id", request.client_id.to_string()),
+        ("access_token_field", request.access_token_field.to_string()),
     ];
-    if let Some(verifier) = code_verifier {
+    if let Some(verifier) = request.code_verifier {
         params.push(("code_verifier", verifier.to_string()));
     }
+    if let Some(secret) = request.client_secret {
+        params.push(("client_secret", secret.to_string()));
+    }
+    for (key, value) in request.extra_token_params {
+        params.push((key.as_str(), value.clone()));
+    }
 
     let response = client
         .post(&exchange_url)
-        .bearer_auth(gateway_token)
+        .bearer_auth(request.gateway_token)
         .form(&params)
         .send()
         .await
@@ -576,7 +722,7 @@ pub async fn exchange_via_proxy(
         .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
 
     let access_token = token_data
-        .get(access_token_field)
+        .get(request.access_token_field)
         .and_then(|v| v.as_str())
         .ok_or_else(|| {
             let fields: Vec<&str> = token_data
@@ -585,7 +731,7 @@ pub async fn exchange_via_proxy(
                 .unwrap_or_default();
             OAuthCallbackError::Io(format!(
                 "No '{}' field in proxy response (fields present: {:?})",
-                access_token_field, fields
+                request.access_token_field, fields
             ))
         })?
         .to_string();
@@ -605,14 +751,10 @@ pub async fn exchange_via_proxy(
 
 #[cfg(test)]
 mod tests {
-    use std::sync::Mutex;
-
     use crate::cli::oauth_defaults::{
         builtin_credentials, callback_host, callback_url, is_loopback_host, landing_html,
     };
-
-    /// Serializes env-mutating tests to prevent parallel races.
-    static ENV_MUTEX: Mutex<()> = Mutex::new(());
+    use crate::config::helpers::ENV_MUTEX;
 
     #[test]
     fn test_is_loopback_host() {
@@ -935,7 +1077,7 @@ mod tests {
 
     #[test]
     fn test_build_platform_state_with_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};
 
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -943,7 +1085,11 @@ mod tests {
         unsafe {
             std::env::set_var("IRONCLAW_INSTANCE_NAME", "kind-deer");
         }
-        assert_eq!(build_platform_state("abc123"), "kind-deer:abc123");
+        let encoded = build_platform_state("abc123");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name.as_deref(), Some("kind-deer"));
+        assert!(!decoded.is_legacy);
         unsafe {
             if let Some(val) = original {
                 std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -955,7 +1101,7 @@ mod tests {
 
     #[test]
     fn test_build_platform_state_without_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};
 
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -965,7 +1111,11 @@ mod tests {
             std::env::remove_var("IRONCLAW_INSTANCE_NAME");
             std::env::remove_var("OPENCLAW_INSTANCE_NAME");
         }
-        assert_eq!(build_platform_state("abc123"), "abc123");
+        let encoded = build_platform_state("abc123");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name, None);
+        assert!(!decoded.is_legacy);
         unsafe {
             if let Some(val) = original {
                 std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -978,7 +1128,7 @@ mod tests {
 
     #[test]
     fn test_build_platform_state_with_openclaw_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};
 
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         let original_ic = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -988,7 +1138,11 @@ mod tests {
             std::env::remove_var("IRONCLAW_INSTANCE_NAME");
             std::env::set_var("OPENCLAW_INSTANCE_NAME", "quiet-lion");
         }
-        assert_eq!(build_platform_state("xyz789"), "quiet-lion:xyz789");
+        let encoded = build_platform_state("xyz789");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "xyz789");
+        assert_eq!(decoded.instance_name.as_deref(), Some("quiet-lion"));
+        assert!(!decoded.is_legacy);
         unsafe {
             if let Some(val) = original_ic {
                 std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -1017,6 +1171,42 @@ mod tests {
         assert_eq!(strip_instance_prefix(""), "");
     }
 
+    #[test]
+    fn test_decode_hosted_oauth_state_accepts_legacy_formats() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let decoded = decode_hosted_oauth_state("kind-deer:abc123").expect("legacy prefixed");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name.as_deref(), Some("kind-deer"));
+        assert!(decoded.is_legacy);
+
+        let decoded = decode_hosted_oauth_state("abc123").expect("legacy raw");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name, None);
+        assert!(decoded.is_legacy);
+    }
+
+    #[test]
+    fn test_decode_hosted_oauth_state_falls_back_for_non_envelope_ic2_prefix() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let decoded =
+            decode_hosted_oauth_state("ic2.provider-owned-state").expect("prefixed fallback");
+        assert_eq!(decoded.flow_id, "ic2.provider-owned-state");
+        assert_eq!(decoded.instance_name, None);
+        assert!(decoded.is_legacy);
+    }
+
+    #[test]
+    fn test_decode_hosted_oauth_state_rejects_tampered_checksum() {
+        use crate::cli::oauth_defaults::{decode_hosted_oauth_state, encode_hosted_oauth_state};
+
+        let encoded = encode_hosted_oauth_state("abc123", Some("kind-deer"));
+        let tampered = format!("{encoded}broken");
+        let err = decode_hosted_oauth_state(&tampered).expect_err("tampered state should fail");
+        assert!(err.contains("checksum"), "unexpected error: {err}");
+    }
+
     /// Verify that `build_oauth_url` includes the RFC 8707 `resource` parameter
     /// when passed through `extra_params`, which is how MCP OAuth gateway mode
     /// scopes tokens to a specific MCP server.

src/cli/tool.rs

@@ -651,8 +651,8 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho
 
     // Check for OAuth configuration
     if let Some(ref oauth) = auth.oauth {
-        // For providers with shared tokens (e.g., all Google tools share google_oauth_token),
-        // combine scopes from all installed tools so one auth covers everything.
+        // For providers with shared tokens, combine scopes from all installed
+        // tools so one auth covers everything.
         let combined = combine_provider_scopes(&tools_dir, &auth.secret_name, oauth).await;
         if combined.scopes.len() > oauth.scopes.len() {
             let extra = combined.scopes.len() - oauth.scopes.len();
@@ -670,8 +670,8 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho
 }
 
 /// Scan the tools directory for all capabilities files sharing the same secret_name
-/// and combine their OAuth scopes. This way, authing any Google tool requests scopes
-/// for ALL installed Google tools, so one login covers everything.
+/// and combine their OAuth scopes so one authorization covers the full shared
+/// credential set.
 async fn combine_provider_scopes(
     tools_dir: &Path,
     secret_name: &str,
@@ -736,11 +736,18 @@ async fn auth_tool_oauth(
         })
         .or_else(|| builtin.as_ref().map(|c| c.client_id.to_string()))
         .ok_or_else(|| {
-            anyhow::anyhow!(
+            let mut message = format!(
                 "OAuth client_id not configured.\n\
-                 Set {} env var, or build with IRONCLAW_GOOGLE_CLIENT_ID.",
+                 Set {} env var",
                 oauth.client_id_env.as_deref().unwrap_or("the client_id")
-            )
+            );
+            if let Some(override_env) =
+                oauth_defaults::builtin_client_id_override_env(&auth.secret_name)
+            {
+                message.push_str(&format!(", or build with {override_env}"));
+            }
+            message.push('.');
+            anyhow::anyhow!(message)
         })?;
 
     // Get client_secret: capabilities file > runtime env var > built-in defaults

src/config/embeddings.rs

@@ -8,6 +8,9 @@ use crate::llm::SessionManager;
 use crate::settings::Settings;
 use crate::workspace::EmbeddingProvider;
 
+/// Default maximum number of cached embeddings.
+pub const DEFAULT_EMBEDDING_CACHE_SIZE: usize = 10_000;
+
 /// Embeddings provider configuration.
 #[derive(Debug, Clone)]
 pub struct EmbeddingsConfig {
@@ -26,6 +29,12 @@ pub struct EmbeddingsConfig {
     /// Custom base URL for OpenAI-compatible embedding providers.
     /// When set, overrides the default `https://api.openai.com`.
     pub openai_base_url: Option<String>,
+    /// Maximum entries in the embedding LRU cache (default 10,000).
+    ///
+    /// Approximate raw embedding payload: `cache_size × dimension × 4 bytes`.
+    /// 10,000 × 1536 floats ≈ 58 MB (payload only; actual memory is higher
+    /// due to HashMap buckets, per-entry Vec/timestamp overhead).
+    pub cache_size: usize,
 }
 
 impl Default for EmbeddingsConfig {
@@ -40,6 +49,7 @@ impl Default for EmbeddingsConfig {
             ollama_base_url: "http://localhost:11434".to_string(),
             dimension,
             openai_base_url: None,
+            cache_size: DEFAULT_EMBEDDING_CACHE_SIZE,
         }
     }
 }
@@ -80,6 +90,15 @@ impl EmbeddingsConfig {
 
         let openai_base_url = optional_env("EMBEDDING_BASE_URL")?;
 
+        let cache_size = parse_optional_env("EMBEDDING_CACHE_SIZE", DEFAULT_EMBEDDING_CACHE_SIZE)?;
+
+        if cache_size == 0 {
+            return Err(ConfigError::InvalidValue {
+                key: "EMBEDDING_CACHE_SIZE".to_string(),
+                message: "must be at least 1".to_string(),
+            });
+        }
+
         Ok(Self {
             enabled,
             provider,
@@ -88,6 +107,7 @@ impl EmbeddingsConfig {
             ollama_base_url,
             dimension,
             openai_base_url,
+            cache_size,
         })
     }
 
@@ -183,13 +203,13 @@ mod tests {
             std::env::remove_var("EMBEDDING_MODEL");
             std::env::remove_var("OPENAI_API_KEY");
             std::env::remove_var("EMBEDDING_BASE_URL");
+            std::env::remove_var("EMBEDDING_CACHE_SIZE");
         }
     }
 
     #[test]
     fn embeddings_disabled_not_overridden_by_openai_key() {
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
-
         clear_embedding_env();
         // SAFETY: Under ENV_MUTEX, no concurrent env access.
         unsafe {
@@ -240,7 +260,6 @@ mod tests {
     #[test]
     fn embeddings_env_override_takes_precedence() {
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
-
         clear_embedding_env();
         // SAFETY: Under ENV_MUTEX.
         unsafe {
@@ -281,10 +300,8 @@ mod tests {
         let config = EmbeddingsConfig::resolve(&settings).expect("resolve should succeed");
         assert_eq!(
             config.openai_base_url.as_deref(),
-            Some("https://custom.example.com"),
-            "EMBEDDING_BASE_URL env var should be parsed into openai_base_url"
+            Some("https://custom.example.com")
         );
-
         // SAFETY: Under ENV_MUTEX.
         unsafe {
             std::env::remove_var("EMBEDDING_BASE_URL");
@@ -303,4 +320,24 @@ mod tests {
             "openai_base_url should be None when EMBEDDING_BASE_URL is not set"
         );
     }
+
+    #[test]
+    fn cache_size_zero_rejected() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_embedding_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("EMBEDDING_CACHE_SIZE", "0");
+        }
+
+        let settings = Settings::default();
+        let result = EmbeddingsConfig::resolve(&settings);
+        assert!(result.is_err(), "cache_size=0 should be rejected");
+        let err = result.unwrap_err().to_string();
+        assert!(err.contains("at least 1"), "should mention minimum: {err}");
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::remove_var("EMBEDDING_CACHE_SIZE");
+        }
+    }
 }

src/config/mod.rs

@@ -38,7 +38,7 @@ pub use self::channels::{
     ChannelsConfig, CliConfig, DEFAULT_GATEWAY_PORT, GatewayConfig, HttpConfig, SignalConfig,
 };
 pub use self::database::{DatabaseBackend, DatabaseConfig, SslMode, default_libsql_path};
-pub use self::embeddings::EmbeddingsConfig;
+pub use self::embeddings::{DEFAULT_EMBEDDING_CACHE_SIZE, EmbeddingsConfig};
 pub use self::heartbeat::HeartbeatConfig;
 pub use self::hygiene::HygieneConfig;
 pub use self::llm::default_session_path;

src/config/relay.rs

@@ -7,7 +7,7 @@ use secrecy::SecretString;
 pub struct RelayConfig {
     /// Base URL of the channel-relay service (e.g., `http://localhost:3001`).
     pub url: String,
-    /// API key for authenticated channel-relay endpoints.
+    /// Bearer token for authenticated channel-relay endpoints (`sk-agent-*`).
     pub api_key: SecretString,
     /// Override for the OAuth callback URL (e.g., a tunnel URL).
     pub callback_url: Option<String>,
@@ -15,12 +15,8 @@ pub struct RelayConfig {
     pub instance_id: Option<String>,
     /// HTTP request timeout in seconds (default: 30).
     pub request_timeout_secs: u64,
-    /// SSE stream long-poll timeout in seconds (default: 86400 = 24 h).
-    pub stream_timeout_secs: u64,
-    /// Initial exponential backoff in milliseconds (default: 1000).
-    pub backoff_initial_ms: u64,
-    /// Maximum exponential backoff in milliseconds (default: 60000).
-    pub backoff_max_ms: u64,
+    /// Path for the webhook callback endpoint (default: `/relay/events`).
+    pub webhook_path: String,
 }
 
 impl std::fmt::Debug for RelayConfig {
@@ -31,9 +27,7 @@ impl std::fmt::Debug for RelayConfig {
             .field("callback_url", &self.callback_url)
             .field("instance_id", &self.instance_id)
             .field("request_timeout_secs", &self.request_timeout_secs)
-            .field("stream_timeout_secs", &self.stream_timeout_secs)
-            .field("backoff_initial_ms", &self.backoff_initial_ms)
-            .field("backoff_max_ms", &self.backoff_max_ms)
+            .field("webhook_path", &self.webhook_path)
             .finish()
     }
 }
@@ -41,8 +35,10 @@ impl std::fmt::Debug for RelayConfig {
 impl RelayConfig {
     /// Load relay config from environment variables.
     ///
-    /// Returns `None` if either `CHANNEL_RELAY_URL` or `CHANNEL_RELAY_API_KEY`
-    /// is not set, making the relay integration opt-in.
+    /// Returns `None` if either of the required env vars (`CHANNEL_RELAY_URL`,
+    /// `CHANNEL_RELAY_API_KEY`) is not set, making the relay integration opt-in.
+    /// The signing secret is fetched from channel-relay at activation time via
+    /// the authenticated `/relay/signing-secret` endpoint — no env var required.
     pub fn from_env() -> Option<Self> {
         Self::from_env_reader(|key| std::env::var(key).ok())
     }
@@ -55,9 +51,7 @@ impl RelayConfig {
             callback_url: None,
             instance_id: None,
             request_timeout_secs: 30,
-            stream_timeout_secs: 86400,
-            backoff_initial_ms: 1000,
-            backoff_max_ms: 60000,
+            webhook_path: "/relay/events".into(),
         }
     }
 
@@ -73,15 +67,7 @@ impl RelayConfig {
             request_timeout_secs: env("RELAY_REQUEST_TIMEOUT_SECS")
                 .and_then(|v| v.parse().ok())
                 .unwrap_or(30),
-            stream_timeout_secs: env("RELAY_STREAM_TIMEOUT_SECS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(86400),
-            backoff_initial_ms: env("RELAY_BACKOFF_INITIAL_MS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(1000),
-            backoff_max_ms: env("RELAY_BACKOFF_MAX_MS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(60000),
+            webhook_path: env("RELAY_WEBHOOK_PATH").unwrap_or_else(|| "/relay/events".into()),
         })
     }
 }
@@ -97,7 +83,21 @@ mod tests {
     }
 
     #[test]
-    fn from_env_reader_loads_defaults() {
+    fn from_env_reader_requires_only_url_and_api_key() {
+        // Signing secret is fetched at activation time — only URL + API key needed.
+        let config = RelayConfig::from_env_reader(|key| match key {
+            "CHANNEL_RELAY_URL" => Some("http://localhost:3001".into()),
+            "CHANNEL_RELAY_API_KEY" => Some("test-key".into()),
+            _ => None,
+        });
+        assert!(
+            config.is_some(),
+            "relay config should load with just URL + API key"
+        );
+    }
+
+    #[test]
+    fn from_env_reader_loads_all_required() {
         let config = RelayConfig::from_env_reader(|key| match key {
             "CHANNEL_RELAY_URL" => Some("http://localhost:3001".into()),
             "CHANNEL_RELAY_API_KEY" => Some("test-key".into()),
@@ -107,9 +107,7 @@ mod tests {
 
         assert_eq!(config.url, "http://localhost:3001");
         assert_eq!(config.request_timeout_secs, 30);
-        assert_eq!(config.stream_timeout_secs, 86400);
-        assert_eq!(config.backoff_initial_ms, 1000);
-        assert_eq!(config.backoff_max_ms, 60000);
+        assert_eq!(config.webhook_path, "/relay/events");
         assert!(config.callback_url.is_none());
         assert!(config.instance_id.is_none());
     }
@@ -122,9 +120,7 @@ mod tests {
             "IRONCLAW_OAUTH_CALLBACK_URL" => Some("https://tunnel.example.com".into()),
             "IRONCLAW_INSTANCE_ID" => Some("my-instance".into()),
             "RELAY_REQUEST_TIMEOUT_SECS" => Some("60".into()),
-            "RELAY_STREAM_TIMEOUT_SECS" => Some("43200".into()),
-            "RELAY_BACKOFF_INITIAL_MS" => Some("2000".into()),
-            "RELAY_BACKOFF_MAX_MS" => Some("120000".into()),
+            "RELAY_WEBHOOK_PATH" => Some("/custom/events".into()),
             _ => None,
         })
         .expect("config should be Some");
@@ -135,9 +131,7 @@ mod tests {
         );
         assert_eq!(config.instance_id.as_deref(), Some("my-instance"));
         assert_eq!(config.request_timeout_secs, 60);
-        assert_eq!(config.stream_timeout_secs, 43200);
-        assert_eq!(config.backoff_initial_ms, 2000);
-        assert_eq!(config.backoff_max_ms, 120000);
+        assert_eq!(config.webhook_path, "/custom/events");
     }
 
     #[test]
@@ -148,7 +142,7 @@ mod tests {
     }
 
     #[test]
-    fn debug_redacts_api_key() {
+    fn debug_redacts_secrets() {
         let config = RelayConfig::from_values("http://localhost:3001", "super-secret");
         let debug = format!("{:?}", config);
         assert!(debug.contains("[REDACTED]"));

src/context/fallback.rs

@@ -0,0 +1,319 @@
+//! Structured fallback deliverables for failed or stuck jobs.
+//!
+//! When a job fails or is detected as stuck, a [`FallbackDeliverable`] captures
+//! what was accomplished before the failure: partial results, action statistics,
+//! cost, and timing. This gives users visibility into terminal jobs instead of
+//! just an error string.
+//!
+//! Fallback deliverables are stored in `JobContext.metadata["fallback_deliverable"]`
+//! and surfaced through the `job_status` tool.
+
+use serde::{Deserialize, Serialize};
+
+use crate::context::memory::Memory;
+use crate::context::state::JobContext;
+
+/// Structured summary of a failed or stuck job.
+///
+/// Stored in `JobContext.metadata["fallback_deliverable"]` when a job fails
+/// or is marked stuck. Surfaced through the `job_status` tool.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct FallbackDeliverable {
+    /// True if at least one action succeeded before failure.
+    pub partial: bool,
+    /// Why the job failed.
+    pub failure_reason: String,
+    /// Last action taken before failure.
+    pub last_action: Option<LastAction>,
+    /// Aggregate action statistics.
+    pub action_stats: ActionStats,
+    /// Total tokens consumed.
+    pub tokens_used: u64,
+    /// Total cost incurred (decimal as string for JSON safety).
+    pub cost: String,
+    /// Wall-clock elapsed time in seconds.
+    pub elapsed_secs: f64,
+    /// Number of self-repair attempts.
+    pub repair_attempts: u32,
+}
+
+/// Summary of the last action taken before failure.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct LastAction {
+    pub tool_name: String,
+    /// Truncated to 200 bytes (UTF-8 safe).
+    pub output_preview: String,
+    pub success: bool,
+}
+
+/// Aggregate action counts.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ActionStats {
+    pub total: u32,
+    pub successful: u32,
+    pub failed: u32,
+}
+
+impl FallbackDeliverable {
+    /// Build a fallback deliverable from a job context and its memory.
+    pub fn build(ctx: &JobContext, memory: &Memory, reason: &str) -> Self {
+        let successful = memory.successful_actions() as u32;
+        let failed = memory.failed_actions() as u32;
+        let total = memory.actions.len() as u32;
+
+        let last_action = memory.last_action().map(|a| {
+            // Use sanitized output to avoid leaking secrets through the fallback API surface.
+            // For failed actions (no sanitized output), fall back to the error message.
+            // Borrow the string slice directly when possible to avoid cloning
+            // potentially large outputs just for truncation.
+            let owned_fallback;
+            let preview_str: &str = if let Some(v) = a.output_sanitized.as_ref() {
+                match v {
+                    serde_json::Value::String(s) => s.as_str(),
+                    other => {
+                        owned_fallback = serde_json::to_string(other).unwrap_or_default();
+                        &owned_fallback
+                    }
+                }
+            } else if let Some(ref err) = a.error {
+                err.as_str()
+            } else {
+                ""
+            };
+            let preview = truncate_str(preview_str, 200);
+            LastAction {
+                tool_name: a.tool_name.clone(),
+                output_preview: preview.to_string(),
+                success: a.success,
+            }
+        });
+
+        let elapsed_secs = ctx.elapsed().map_or(0.0, |d| d.as_secs_f64());
+
+        Self {
+            partial: successful > 0,
+            failure_reason: truncate_str(reason, 1000).to_string(),
+            last_action,
+            action_stats: ActionStats {
+                total,
+                successful,
+                failed,
+            },
+            tokens_used: ctx.total_tokens_used,
+            cost: ctx.actual_cost.to_string(),
+            elapsed_secs,
+            repair_attempts: ctx.repair_attempts,
+        }
+    }
+}
+
+/// Truncate a string to at most `max_len` bytes on a char boundary.
+fn truncate_str(s: &str, max_len: usize) -> &str {
+    &s[..crate::util::floor_char_boundary(s, max_len)]
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::context::memory::Memory;
+    use crate::context::state::JobContext;
+    use chrono::{Duration, Utc};
+    use rust_decimal::Decimal;
+    use std::time::Duration as StdDuration;
+
+    #[test]
+    fn test_fallback_zero_actions() {
+        let ctx = JobContext::new("Test", "Empty job");
+        let memory = Memory::new(ctx.job_id);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "timed out");
+
+        assert!(!fb.partial); // safety: test
+        assert_eq!(fb.failure_reason, "timed out"); // safety: test
+        assert!(fb.last_action.is_none()); // safety: test
+        assert_eq!(fb.action_stats.total, 0); // safety: test
+        assert_eq!(fb.action_stats.successful, 0); // safety: test
+        assert_eq!(fb.action_stats.failed, 0); // safety: test
+        assert_eq!(fb.tokens_used, 0); // safety: test
+        assert_eq!(fb.cost, "0"); // safety: test
+        assert_eq!(fb.repair_attempts, 0); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_mixed_actions() {
+        let mut ctx = JobContext::new("Test", "Mixed job");
+        ctx.total_tokens_used = 5000;
+        ctx.actual_cost = Decimal::new(42, 2); // 0.42
+        ctx.repair_attempts = 1;
+
+        let mut memory = Memory::new(ctx.job_id);
+
+        // 3 successes
+        for _ in 0..3 {
+            let action = memory
+                .create_action("tool_a", serde_json::json!({}))
+                .succeed(
+                    Some("output".to_string()),
+                    serde_json::json!({}),
+                    StdDuration::from_secs(1),
+                );
+            memory.record_action(action);
+        }
+        // 2 failures
+        for _ in 0..2 {
+            let action = memory
+                .create_action("tool_b", serde_json::json!({}))
+                .fail("broke", StdDuration::from_secs(1));
+            memory.record_action(action);
+        }
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "max iterations");
+
+        assert!(fb.partial); // safety: test
+        assert_eq!(fb.action_stats.total, 5); // safety: test
+        assert_eq!(fb.action_stats.successful, 3); // safety: test
+        assert_eq!(fb.action_stats.failed, 2); // safety: test
+        assert_eq!(fb.tokens_used, 5000); // safety: test
+        assert_eq!(fb.cost, "0.42"); // safety: test
+        assert_eq!(fb.repair_attempts, 1); // safety: test
+        assert!(fb.last_action.is_some()); // safety: test
+        let la = fb.last_action.unwrap(); // safety: test
+        assert_eq!(la.tool_name, "tool_b"); // safety: test
+        assert!(!la.success); // safety: test
+        // Failed actions should surface the error message as the output preview
+        assert_eq!(la.output_preview, "broke"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_failed_action_shows_error() {
+        let ctx = JobContext::new("Test", "Error preview");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let action = memory
+            .create_action("broken_tool", serde_json::json!({}))
+            .fail("connection timed out after 30s", StdDuration::from_secs(30));
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "tool failure");
+        let la = fb.last_action.unwrap(); // safety: test
+        assert!(!la.success); // safety: test
+        assert_eq!(la.output_preview, "connection timed out after 30s"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_last_action_truncation() {
+        let ctx = JobContext::new("Test", "Truncation");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let long_output = "x".repeat(500);
+        let action = memory
+            .create_action("tool_c", serde_json::json!({}))
+            .succeed(
+                Some(long_output.clone()),
+                serde_json::Value::String(long_output),
+                StdDuration::from_secs(1),
+            );
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        let la = fb.last_action.unwrap(); // safety: test
+        assert!(la.output_preview.len() <= 200); // safety: test
+        assert!(!la.output_preview.is_empty()); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_uses_sanitized_output() {
+        let ctx = JobContext::new("Test", "Sanitized");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let action = memory
+            .create_action("tool_d", serde_json::json!({}))
+            .succeed(
+                Some("[REDACTED]".to_string()),
+                serde_json::json!({"api_key": "sk-secret-key-12345"}),
+                StdDuration::from_secs(1),
+            );
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        let la = fb.last_action.unwrap(); // safety: test
+        // Must use sanitized output, not raw
+        assert!(!la.output_preview.contains("sk-secret")); // safety: test
+        assert!(la.output_preview.contains("REDACTED")); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_elapsed_time() {
+        let mut ctx = JobContext::new("Test", "Timing");
+        let now = Utc::now();
+        ctx.started_at = Some(now - Duration::seconds(10));
+        ctx.completed_at = Some(now);
+
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+
+        // Should be approximately 10 seconds
+        assert!((fb.elapsed_secs - 10.0).abs() < 0.1); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_no_started_at() {
+        let ctx = JobContext::new("Test", "Never started");
+        let memory = Memory::new(ctx.job_id);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        assert!((fb.elapsed_secs - 0.0).abs() < 0.001); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_elapsed_time_no_completed_at() {
+        let mut ctx = JobContext::new("Test", "Still running");
+        ctx.started_at = Some(Utc::now() - Duration::seconds(5));
+        // completed_at is None — should use Utc::now() as fallback
+
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "stuck");
+
+        // Should be approximately 5 seconds (using now as end time)
+        assert!(fb.elapsed_secs >= 4.0 && fb.elapsed_secs <= 7.0); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_failure_reason_truncation() {
+        let ctx = JobContext::new("Test", "Long reason");
+        let memory = Memory::new(ctx.job_id);
+
+        let long_reason = "x".repeat(5000);
+        let fb = FallbackDeliverable::build(&ctx, &memory, &long_reason);
+
+        assert!(fb.failure_reason.len() <= 1000); // safety: test
+        assert!(!fb.failure_reason.is_empty()); // safety: test
+    }
+
+    #[test]
+    fn test_truncate_str_ascii() {
+        assert_eq!(truncate_str("hello", 10), "hello"); // safety: test
+        assert_eq!(truncate_str("hello world", 5), "hello"); // safety: test
+    }
+
+    #[test]
+    fn test_truncate_str_unicode() {
+        // "é" is 2 bytes in UTF-8
+        let s = "café";
+        assert_eq!(truncate_str(s, 10), "café"); // safety: test
+        // Truncating at 4 would split "é", should back up to 3
+        assert_eq!(truncate_str(s, 4), "caf"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_serialization() {
+        let ctx = JobContext::new("Test", "Serialize");
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "test error");
+
+        // Should serialize to JSON and back without error
+        let json = serde_json::to_value(&fb).unwrap(); // safety: test
+        let deserialized: FallbackDeliverable = serde_json::from_value(json).unwrap(); // safety: test
+        assert_eq!(deserialized.failure_reason, "test error"); // safety: test
+    }
+}

src/context/memory.rs

@@ -58,15 +58,19 @@ impl ActionRecord {
     }
 
     /// Mark the action as successful.
+    ///
+    /// `output_sanitized` is the tool output after safety processing (string).
+    /// `output_raw` is the original tool result (JSON value, stored as a
+    /// pretty-printed JSON string in `ActionRecord.output_raw`).
     pub fn succeed(
         mut self,
-        output_raw: Option<String>,
-        output_sanitized: serde_json::Value,
+        output_sanitized: Option<String>,
+        output_raw: serde_json::Value,
         duration: Duration,
     ) -> Self {
         self.success = true;
-        self.output_raw = output_raw;
-        self.output_sanitized = Some(output_sanitized);
+        self.output_raw = Some(serde_json::to_string_pretty(&output_raw).unwrap_or_default());
+        self.output_sanitized = output_sanitized.map(serde_json::Value::String);
         self.duration = duration;
         self
     }
@@ -248,15 +252,15 @@ mod tests {
     #[test]
     fn test_action_record() {
         let action = ActionRecord::new(0, "test", serde_json::json!({"key": "value"}));
-        assert_eq!(action.sequence, 0);
-        assert!(!action.success);
+        assert_eq!(action.sequence, 0); // safety: test
+        assert!(!action.success); // safety: test
 
         let action = action.succeed(
             Some("raw".to_string()),
             serde_json::json!({"result": "ok"}),
             Duration::from_millis(100),
         );
-        assert!(action.success);
+        assert!(action.success); // safety: test
     }
 
     #[test]
@@ -267,7 +271,7 @@ mod tests {
         memory.add(ChatMessage::user("How are you?"));
         memory.add(ChatMessage::assistant("Good!"));
 
-        assert_eq!(memory.len(), 3); // Oldest removed
+        assert_eq!(memory.len(), 3); // Oldest removed // safety: test
     }
 
     #[test]
@@ -286,9 +290,9 @@ mod tests {
             .with_cost(Decimal::new(20, 1));
         memory.record_action(action2);
 
-        assert_eq!(memory.total_cost(), Decimal::new(30, 1));
-        assert_eq!(memory.total_duration(), Duration::from_secs(3));
-        assert_eq!(memory.successful_actions(), 2);
+        assert_eq!(memory.total_cost(), Decimal::new(30, 1)); // safety: test
+        assert_eq!(memory.total_duration(), Duration::from_secs(3)); // safety: test
+        assert_eq!(memory.successful_actions(), 2); // safety: test
     }
 
     #[test]
@@ -296,11 +300,11 @@ mod tests {
         let action = ActionRecord::new(1, "broken_tool", serde_json::json!({"x": 1}));
         let action = action.fail("something went wrong", Duration::from_millis(50));
 
-        assert!(!action.success);
-        assert_eq!(action.error.as_deref(), Some("something went wrong"));
-        assert_eq!(action.duration, Duration::from_millis(50));
-        assert!(action.output_raw.is_none());
-        assert!(action.output_sanitized.is_none());
+        assert!(!action.success); // safety: test
+        assert_eq!(action.error.as_deref(), Some("something went wrong")); // safety: test
+        assert_eq!(action.duration, Duration::from_millis(50)); // safety: test
+        assert!(action.output_raw.is_none()); // safety: test
+        assert!(action.output_sanitized.is_none()); // safety: test
     }
 
     #[test]
@@ -308,9 +312,9 @@ mod tests {
         let action = ActionRecord::new(0, "risky_tool", serde_json::json!({}));
         let action = action.with_warnings(vec!["suspicious pattern".into(), "possible xss".into()]);
 
-        assert_eq!(action.sanitization_warnings.len(), 2);
-        assert_eq!(action.sanitization_warnings[0], "suspicious pattern");
-        assert_eq!(action.sanitization_warnings[1], "possible xss");
+        assert_eq!(action.sanitization_warnings.len(), 2); // safety: test
+        assert_eq!(action.sanitization_warnings[0], "suspicious pattern"); // safety: test
+        assert_eq!(action.sanitization_warnings[1], "possible xss"); // safety: test
     }
 
     #[test]
@@ -319,41 +323,46 @@ mod tests {
         let cost = Decimal::new(42, 2); // 0.42
         let action = action.with_cost(cost);
 
-        assert_eq!(action.cost, Some(Decimal::new(42, 2)));
+        assert_eq!(action.cost, Some(Decimal::new(42, 2))); // safety: test
     }
 
     #[test]
     fn test_action_record_new_defaults() {
         let action = ActionRecord::new(5, "my_tool", serde_json::json!({"key": "val"}));
 
-        assert_eq!(action.sequence, 5);
-        assert_eq!(action.tool_name, "my_tool");
-        assert_eq!(action.input, serde_json::json!({"key": "val"}));
-        assert!(!action.success);
-        assert!(action.output_raw.is_none());
-        assert!(action.output_sanitized.is_none());
-        assert!(action.sanitization_warnings.is_empty());
-        assert!(action.cost.is_none());
-        assert_eq!(action.duration, Duration::ZERO);
-        assert!(action.error.is_none());
+        assert_eq!(action.sequence, 5); // safety: test
+        assert_eq!(action.tool_name, "my_tool"); // safety: test
+        assert_eq!(action.input, serde_json::json!({"key": "val"})); // safety: test
+        assert!(!action.success); // safety: test
+        assert!(action.output_raw.is_none()); // safety: test
+        assert!(action.output_sanitized.is_none()); // safety: test
+        assert!(action.sanitization_warnings.is_empty()); // safety: test
+        assert!(action.cost.is_none()); // safety: test
+        assert_eq!(action.duration, Duration::ZERO); // safety: test
+        assert!(action.error.is_none()); // safety: test
     }
 
     #[test]
     fn test_action_record_succeed_sets_fields() {
         let action = ActionRecord::new(0, "tool", serde_json::json!({}));
         let action = action.succeed(
-            Some("raw output here".into()),
+            Some("sanitized output".into()),
             serde_json::json!({"clean": true}),
             Duration::from_secs(7),
         );
 
-        assert!(action.success);
-        assert_eq!(action.output_raw.as_deref(), Some("raw output here"));
+        assert!(action.success); // safety: test
+        // output_raw is the JSON value pretty-printed
+        let expected_raw =
+            serde_json::to_string_pretty(&serde_json::json!({"clean": true})).unwrap(); // safety: test
+        assert_eq!(action.output_raw.as_deref(), Some(expected_raw.as_str())); // safety: test
+        // output_sanitized wraps the string in a JSON string value
         assert_eq!(
+            /* safety: test */
             action.output_sanitized,
-            Some(serde_json::json!({"clean": true}))
+            Some(serde_json::json!("sanitized output"))
         );
-        assert_eq!(action.duration, Duration::from_secs(7));
+        assert_eq!(action.duration, Duration::from_secs(7)); // safety: test
     }
 
     #[test]
@@ -361,13 +370,13 @@ mod tests {
         let mut mem = ConversationMemory::new(10);
         mem.add(ChatMessage::user("hello"));
         mem.add(ChatMessage::assistant("hi"));
-        assert_eq!(mem.len(), 2);
-        assert!(!mem.is_empty());
+        assert_eq!(mem.len(), 2); // safety: test
+        assert!(!mem.is_empty()); // safety: test
 
         mem.clear();
-        assert_eq!(mem.len(), 0);
-        assert!(mem.is_empty());
-        assert!(mem.messages().is_empty());
+        assert_eq!(mem.len(), 0); // safety: test
+        assert!(mem.is_empty()); // safety: test
+        assert!(mem.messages().is_empty()); // safety: test
     }
 
     #[test]
@@ -379,20 +388,20 @@ mod tests {
         mem.add(ChatMessage::assistant("four"));
 
         let last_2 = mem.last_n(2);
-        assert_eq!(last_2.len(), 2);
-        assert_eq!(last_2[0].content, "three");
-        assert_eq!(last_2[1].content, "four");
+        assert_eq!(last_2.len(), 2); // safety: test
+        assert_eq!(last_2[0].content, "three"); // safety: test
+        assert_eq!(last_2[1].content, "four"); // safety: test
 
         // Requesting more than available returns all
         let last_100 = mem.last_n(100);
-        assert_eq!(last_100.len(), 4);
+        assert_eq!(last_100.len(), 4); // safety: test
     }
 
     #[test]
     fn test_conversation_memory_last_n_empty() {
         let mem = ConversationMemory::new(10);
         let result = mem.last_n(5);
-        assert!(result.is_empty());
+        assert!(result.is_empty()); // safety: test
     }
 
     #[test]
@@ -405,13 +414,13 @@ mod tests {
         // At capacity (3). Adding one more should trim, but keep system.
         mem.add(ChatMessage::user("msg3"));
 
-        assert_eq!(mem.len(), 3);
+        assert_eq!(mem.len(), 3); // safety: test
         // System message must survive
-        assert_eq!(mem.messages()[0].role, crate::llm::Role::System);
-        assert_eq!(mem.messages()[0].content, "You are helpful");
+        assert_eq!(mem.messages()[0].role, crate::llm::Role::System); // safety: test
+        assert_eq!(mem.messages()[0].content, "You are helpful"); // safety: test
         // Oldest non-system message (msg1) should be gone
-        assert_eq!(mem.messages()[1].content, "msg2");
-        assert_eq!(mem.messages()[2].content, "msg3");
+        assert_eq!(mem.messages()[1].content, "msg2"); // safety: test
+        assert_eq!(mem.messages()[2].content, "msg3"); // safety: test
     }
 
     #[test]
@@ -422,9 +431,9 @@ mod tests {
         // Now at capacity. Add another.
         mem.add(ChatMessage::user("b"));
 
-        assert_eq!(mem.len(), 2);
-        assert_eq!(mem.messages()[0].role, crate::llm::Role::System);
-        assert_eq!(mem.messages()[1].content, "b");
+        assert_eq!(mem.len(), 2); // safety: test
+        assert_eq!(mem.messages()[0].role, crate::llm::Role::System); // safety: test
+        assert_eq!(mem.messages()[1].content, "b"); // safety: test
     }
 
     #[test]
@@ -440,7 +449,7 @@ mod tests {
         mem.add(ChatMessage::user("hello"));
         // Should have broken out rather than looping forever.
         // The system message is protected, so len may exceed max.
-        assert!(mem.len() <= 2);
+        assert!(mem.len() <= 2); // safety: test
     }
 
     #[test]
@@ -459,14 +468,14 @@ mod tests {
             .fail("oops", Duration::from_millis(2));
         memory.record_action(err);
 
-        assert_eq!(memory.successful_actions(), 1);
-        assert_eq!(memory.failed_actions(), 1);
+        assert_eq!(memory.successful_actions(), 1); // safety: test
+        assert_eq!(memory.failed_actions(), 1); // safety: test
     }
 
     #[test]
     fn test_memory_last_action() {
         let mut memory = Memory::new(Uuid::new_v4());
-        assert!(memory.last_action().is_none());
+        assert!(memory.last_action().is_none()); // safety: test
 
         let a1 = memory
             .create_action("first", serde_json::json!({}))
@@ -478,8 +487,8 @@ mod tests {
             .fail("nope", Duration::ZERO);
         memory.record_action(a2);
 
-        let last = memory.last_action().unwrap();
-        assert_eq!(last.tool_name, "second");
+        let last = memory.last_action().unwrap(); // safety: test
+        assert_eq!(last.tool_name, "second"); // safety: test
     }
 
     #[test]
@@ -499,9 +508,9 @@ mod tests {
         );
         memory.record_action(a);
 
-        assert_eq!(memory.actions_by_tool("shell").len(), 3);
-        assert_eq!(memory.actions_by_tool("http").len(), 1);
-        assert_eq!(memory.actions_by_tool("nonexistent").len(), 0);
+        assert_eq!(memory.actions_by_tool("shell").len(), 3); // safety: test
+        assert_eq!(memory.actions_by_tool("http").len(), 1); // safety: test
+        assert_eq!(memory.actions_by_tool("nonexistent").len(), 0); // safety: test
     }
 
     #[test]
@@ -509,25 +518,25 @@ mod tests {
         let mut memory = Memory::new(Uuid::new_v4());
 
         let a0 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a0.sequence, 0);
+        assert_eq!(a0.sequence, 0); // safety: test
 
         let a1 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a1.sequence, 1);
+        assert_eq!(a1.sequence, 1); // safety: test
 
         let a2 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a2.sequence, 2);
+        assert_eq!(a2.sequence, 2); // safety: test
     }
 
     #[test]
     fn test_memory_add_message_delegates_to_conversation() {
         let mut memory = Memory::new(Uuid::new_v4());
-        assert!(memory.conversation.is_empty());
+        assert!(memory.conversation.is_empty()); // safety: test
 
         memory.add_message(ChatMessage::user("hello"));
         memory.add_message(ChatMessage::assistant("hi"));
 
-        assert_eq!(memory.conversation.len(), 2);
-        assert_eq!(memory.conversation.messages()[0].content, "hello");
+        assert_eq!(memory.conversation.len(), 2); // safety: test
+        assert_eq!(memory.conversation.messages()[0].content, "hello"); // safety: test
     }
 
     #[test]
@@ -540,7 +549,7 @@ mod tests {
             .succeed(None, serde_json::json!({}), Duration::ZERO);
         memory.record_action(a);
 
-        assert_eq!(memory.total_cost(), Decimal::ZERO);
+        assert_eq!(memory.total_cost(), Decimal::ZERO); // safety: test
     }
 
     #[test]
@@ -560,6 +569,6 @@ mod tests {
         memory.record_action(a2);
 
         // Both successful and failed actions contribute to total duration
-        assert_eq!(memory.total_duration(), Duration::from_millis(300));
+        assert_eq!(memory.total_duration(), Duration::from_millis(300)); // safety: test
     }
 }

src/context/mod.rs

@@ -6,10 +6,12 @@
 //! - State machine
 //! - Resource tracking
 
+pub mod fallback;
 mod manager;
 mod memory;
 mod state;
 
+pub use fallback::FallbackDeliverable;
 pub use manager::ContextManager;
 pub use memory::{ActionRecord, ConversationMemory, Memory};
 pub use state::{JobContext, JobState, StateTransition, TokenBudgetExceeded};

src/llm/oauth_helpers.rs

@@ -39,9 +39,7 @@ pub enum OAuthCallbackError {
 /// deployments where `127.0.0.1` is unreachable from the user's browser),
 /// then falls back to `http://{callback_host()}:{OAUTH_CALLBACK_PORT}`.
 pub fn callback_url() -> String {
-    std::env::var("IRONCLAW_OAUTH_CALLBACK_URL")
-        .ok()
-        .filter(|v| !v.is_empty())
+    crate::config::helpers::env_or_override("IRONCLAW_OAUTH_CALLBACK_URL")
         .unwrap_or_else(|| format!("http://{}:{}", callback_host(), OAUTH_CALLBACK_PORT))
 }
 
@@ -57,7 +55,8 @@ pub fn callback_url() -> String {
 /// Note: this transmits the session token over plain HTTP — prefer SSH port
 /// forwarding (`ssh -L 9876:127.0.0.1:9876 user@host`) when possible.
 pub fn callback_host() -> String {
-    std::env::var("OAUTH_CALLBACK_HOST").unwrap_or_else(|_| "127.0.0.1".to_string())
+    crate::config::helpers::env_or_override("OAUTH_CALLBACK_HOST")
+        .unwrap_or_else(|| "127.0.0.1".to_string())
 }
 
 /// Returns `true` if `host` is a loopback address that only accepts local connections.

src/orchestrator/api.rs

@@ -333,6 +333,12 @@ async fn job_event_handler(
                 .get("session_id")
                 .and_then(|v| v.as_str())
                 .map(|s| s.to_string()),
+            // NOTE: `fallback_deliverable` is currently always None in SSE events.
+            // In-memory jobs store fallback data in JobContext.metadata (accessed via job_status tool).
+            // Sandbox containers don't yet emit fallback data in their event payloads.
+            // This field is forward-compatible infrastructure for when container workers
+            // gain context/memory tracking capabilities.
+            fallback_deliverable: payload.data.get("fallback_deliverable").cloned(),
         },
         _ => SseEvent::JobStatus {
             job_id: job_id_str,

src/tools/builtin/http.rs

@@ -837,7 +837,7 @@ impl Tool for HttpTool {
             }));
 
         if has_credentials {
-            return ApprovalRequirement::Always;
+            return ApprovalRequirement::UnlessAutoApproved;
         }
 
         // GET requests (or missing method, since GET is the default) are low-risk
@@ -1093,25 +1093,31 @@ mod tests {
     }
 
     #[test]
-    fn test_auth_header_object_format_returns_always() {
+    fn test_auth_header_object_format_returns_unless_auto_approved() {
         let tool = HttpTool::new();
         let params = serde_json::json!({
             "method": "GET",
             "url": "https://api.example.com/data",
             "headers": {"Authorization": "Bearer token123"}
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
     }
 
     #[test]
-    fn test_auth_header_array_format_returns_always() {
+    fn test_auth_header_array_format_returns_unless_auto_approved() {
         let tool = HttpTool::new();
         let params = serde_json::json!({
             "method": "GET",
             "url": "https://api.example.com/data",
             "headers": [{"name": "Authorization", "value": "Bearer token123"}]
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
     }
 
     #[test]
@@ -1124,7 +1130,10 @@ mod tests {
             "url": "https://example.com",
             "headers": {"AUTHORIZATION": "Bearer x"}
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
 
         // Array format with mixed case
         let params = serde_json::json!({
@@ -1132,7 +1141,10 @@ mod tests {
             "url": "https://example.com",
             "headers": [{"name": "X-Api-Key", "value": "key123"}]
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
     }
 
     #[test]
@@ -1161,8 +1173,8 @@ mod tests {
             });
             assert_eq!(
                 tool.requires_approval(&params),
-                ApprovalRequirement::Always,
-                "Header '{}' should trigger Always approval",
+                ApprovalRequirement::UnlessAutoApproved,
+                "Header '{}' should trigger UnlessAutoApproved approval",
                 header_name
             );
         }
@@ -1203,7 +1215,7 @@ mod tests {
     // ── Credential registry approval tests ─────────────────────────────
 
     #[test]
-    fn test_host_with_credential_mapping_returns_always() {
+    fn test_host_with_credential_mapping_returns_unless_auto_approved() {
         use crate::secrets::CredentialMapping;
         use crate::tools::wasm::SharedCredentialRegistry;
 
@@ -1223,7 +1235,10 @@ mod tests {
             "method": "GET",
             "url": "https://api.openai.com/v1/models"
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
     }
 
     #[test]
@@ -1243,24 +1258,55 @@ mod tests {
     }
 
     #[test]
-    fn test_url_query_param_credential_returns_always() {
+    fn test_url_query_param_credential_returns_unless_auto_approved() {
         let tool = HttpTool::new();
         let params = serde_json::json!({
             "method": "GET",
             "url": "https://api.example.com/data?api_key=secret123"
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
     }
 
     #[test]
-    fn test_bearer_value_in_custom_header_returns_always() {
+    fn test_bearer_value_in_custom_header_returns_unless_auto_approved() {
         let tool = HttpTool::new();
         let params = serde_json::json!({
             "method": "GET",
             "url": "https://example.com",
             "headers": {"X-Custom": format!("Bearer {TEST_OPENAI_API_KEY}")}
         });
-        assert_eq!(tool.requires_approval(&params), ApprovalRequirement::Always);
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved
+        );
+    }
+
+    /// Regression test: credentialed HTTP requests must return
+    /// `UnlessAutoApproved` (not `Always`) so that the session auto-approve
+    /// set is respected when the user says "always".
+    #[test]
+    fn test_credentialed_requests_respect_auto_approve() {
+        let tool = HttpTool::new();
+
+        // Manual credentials (Authorization header)
+        let params = serde_json::json!({
+            "method": "GET",
+            "url": "https://api.github.com/orgs/Casa",
+            "headers": {"Authorization": "Bearer ghp_abc123"}
+        });
+        // Must NOT be Always — Always ignores the session auto-approve set
+        assert_ne!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::Always,
+            "Credentialed HTTP requests must not return Always; use UnlessAutoApproved"
+        );
+        assert_eq!(
+            tool.requires_approval(&params),
+            ApprovalRequirement::UnlessAutoApproved,
+        );
     }
 
     #[test]

src/tools/builtin/job.rs

@@ -1005,7 +1005,8 @@ impl Tool for JobStatusTool {
                     "created_at": job_ctx.created_at.to_rfc3339(),
                     "started_at": job_ctx.started_at.map(|t| t.to_rfc3339()),
                     "completed_at": job_ctx.completed_at.map(|t| t.to_rfc3339()),
-                    "actual_cost": job_ctx.actual_cost.to_string()
+                    "actual_cost": job_ctx.actual_cost.to_string(),
+                    "fallback_deliverable": job_ctx.metadata.get("fallback_deliverable"),
                 });
                 Ok(ToolOutput::success(result, start.elapsed()))
             }
@@ -1384,7 +1385,7 @@ mod tests {
         let tool = CreateJobTool::new(manager.clone());
 
         // Without sandbox deps, it should use the local path
-        assert!(!tool.sandbox_enabled());
+        assert!(!tool.sandbox_enabled()); // safety: test
 
         let params = serde_json::json!({
             "title": "Test Job",
@@ -1392,12 +1393,13 @@ mod tests {
         });
 
         let ctx = JobContext::default();
-        let result = tool.execute(params, &ctx).await.unwrap();
+        let result = tool.execute(params, &ctx).await.unwrap(); // safety: test
 
-        let job_id = result.result.get("job_id").unwrap().as_str().unwrap();
-        assert!(!job_id.is_empty());
+        let job_id = result.result.get("job_id").unwrap().as_str().unwrap(); // safety: test
+        assert!(!job_id.is_empty()); // safety: test
         assert_eq!(
-            result.result.get("status").unwrap().as_str().unwrap(),
+            /* safety: test */
+            result.result.get("status").unwrap().as_str().unwrap(), // safety: test
             "pending"
         );
     }
@@ -1409,11 +1411,11 @@ mod tests {
         // Without sandbox
         let tool = CreateJobTool::new(Arc::clone(&manager));
         let schema = tool.parameters_schema();
-        let props = schema.get("properties").unwrap().as_object().unwrap();
-        assert!(props.contains_key("title"));
-        assert!(props.contains_key("description"));
-        assert!(!props.contains_key("wait"));
-        assert!(!props.contains_key("mode"));
+        let props = schema.get("properties").unwrap().as_object().unwrap(); // safety: test
+        assert!(props.contains_key("title")); // safety: test
+        assert!(props.contains_key("description")); // safety: test
+        assert!(!props.contains_key("wait")); // safety: test
+        assert!(!props.contains_key("mode")); // safety: test
     }
 
     #[test]
@@ -1422,7 +1424,7 @@ mod tests {
 
         // Without sandbox: default timeout
         let tool = CreateJobTool::new(Arc::clone(&manager));
-        assert_eq!(tool.execution_timeout(), Duration::from_secs(30));
+        assert_eq!(tool.execution_timeout(), Duration::from_secs(30)); // safety: test
     }
 
     #[tokio::test]
@@ -1455,23 +1457,23 @@ mod tests {
         let manager = Arc::new(ContextManager::new(5));
 
         // Create some jobs
-        manager.create_job("Job 1", "Desc 1").await.unwrap();
-        manager.create_job("Job 2", "Desc 2").await.unwrap();
+        manager.create_job("Job 1", "Desc 1").await.unwrap(); // safety: test
+        manager.create_job("Job 2", "Desc 2").await.unwrap(); // safety: test
 
         let tool = ListJobsTool::new(manager);
 
         let params = serde_json::json!({});
         let ctx = JobContext::default();
-        let result = tool.execute(params, &ctx).await.unwrap();
+        let result = tool.execute(params, &ctx).await.unwrap(); // safety: test
 
-        let jobs = result.result.get("jobs").unwrap().as_array().unwrap();
-        assert_eq!(jobs.len(), 2);
+        let jobs = result.result.get("jobs").unwrap().as_array().unwrap(); // safety: test
+        assert_eq!(jobs.len(), 2); // safety: test
     }
 
     #[tokio::test]
     async fn test_job_status_tool() {
         let manager = Arc::new(ContextManager::new(5));
-        let job_id = manager.create_job("Test Job", "Description").await.unwrap();
+        let job_id = manager.create_job("Test Job", "Description").await.unwrap(); // safety: test
 
         let tool = JobStatusTool::new(manager);
 
@@ -1479,10 +1481,11 @@ mod tests {
             "job_id": job_id.to_string()
         });
         let ctx = JobContext::default();
-        let result = tool.execute(params, &ctx).await.unwrap();
+        let result = tool.execute(params, &ctx).await.unwrap(); // safety: test
 
         assert_eq!(
-            result.result.get("title").unwrap().as_str().unwrap(),
+            /* safety: test */
+            result.result.get("title").unwrap().as_str().unwrap(), // safety: test
             "Test Job"
         );
     }
@@ -1496,8 +1499,9 @@ mod tests {
         let missing_title = tool
             .execute(serde_json::json!({ "description": "A test job" }), &ctx)
             .await;
-        assert!(missing_title.is_err());
+        assert!(missing_title.is_err()); // safety: test
         assert!(
+            /* safety: test */
             missing_title
                 .unwrap_err()
                 .to_string()
@@ -1507,8 +1511,9 @@ mod tests {
         let missing_description = tool
             .execute(serde_json::json!({ "title": "Test Job" }), &ctx)
             .await;
-        assert!(missing_description.is_err());
+        assert!(missing_description.is_err()); // safety: test
         assert!(
+            /* safety: test */
             missing_description
                 .unwrap_err()
                 .to_string()
@@ -1522,19 +1527,19 @@ mod tests {
         let pending_id = manager
             .create_job_for_user("default", "Pending Job", "Todo")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         let completed_id = manager
             .create_job_for_user("default", "Completed Job", "Done")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         let failed_id = manager
             .create_job_for_user("default", "Failed Job", "Oops")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         manager
             .create_job_for_user("other-user", "Other User Job", "Ignore")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         manager
             .update_context(completed_id, |ctx| {
@@ -1542,41 +1547,44 @@ mod tests {
                 ctx.transition_to(JobState::Completed, Some("done".to_string()))
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
         manager
             .update_context(failed_id, |ctx| {
                 ctx.transition_to(JobState::InProgress, None)?;
                 ctx.transition_to(JobState::Failed, Some("boom".to_string()))
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         let tool = ListJobsTool::new(Arc::clone(&manager));
         let ctx = JobContext::default();
-        let result = tool.execute(serde_json::json!({}), &ctx).await.unwrap();
+        let result = tool.execute(serde_json::json!({}), &ctx).await.unwrap(); // safety: test
 
-        let jobs = result.result.get("jobs").unwrap().as_array().unwrap();
-        assert_eq!(jobs.len(), 3);
+        let jobs = result.result.get("jobs").unwrap().as_array().unwrap(); // safety: test
+        assert_eq!(jobs.len(), 3); // safety: test
         assert!(jobs.iter().any(|job| {
+            // safety: test
             job.get("job_id").and_then(|v| v.as_str()) == Some(&pending_id.to_string())
                 && job.get("status").and_then(|v| v.as_str()) == Some("Pending")
         }));
         assert!(jobs.iter().any(|job| {
+            // safety: test
             job.get("job_id").and_then(|v| v.as_str()) == Some(&completed_id.to_string())
                 && job.get("status").and_then(|v| v.as_str()) == Some("Completed")
         }));
         assert!(jobs.iter().any(|job| {
+            // safety: test
             job.get("job_id").and_then(|v| v.as_str()) == Some(&failed_id.to_string())
                 && job.get("status").and_then(|v| v.as_str()) == Some("Failed")
         }));
 
-        let summary = result.result.get("summary").unwrap();
-        assert_eq!(summary.get("total").and_then(|v| v.as_u64()), Some(3));
-        assert_eq!(summary.get("pending").and_then(|v| v.as_u64()), Some(1));
-        assert_eq!(summary.get("completed").and_then(|v| v.as_u64()), Some(1));
-        assert_eq!(summary.get("failed").and_then(|v| v.as_u64()), Some(1));
+        let summary = result.result.get("summary").unwrap(); // safety: test
+        assert_eq!(summary.get("total").and_then(|v| v.as_u64()), Some(3)); // safety: test
+        assert_eq!(summary.get("pending").and_then(|v| v.as_u64()), Some(1)); // safety: test
+        assert_eq!(summary.get("completed").and_then(|v| v.as_u64()), Some(1)); // safety: test
+        assert_eq!(summary.get("failed").and_then(|v| v.as_u64()), Some(1)); // safety: test
     }
 
     #[tokio::test]
@@ -1585,29 +1593,30 @@ mod tests {
         let job_id = manager
             .create_job_for_user("default", "Transition Job", "Track me")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         manager
             .update_context(job_id, |ctx| {
                 ctx.transition_to(JobState::InProgress, Some("started".to_string()))?;
                 ctx.transition_to(JobState::Completed, Some("finished".to_string()))
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         let tool = JobStatusTool::new(Arc::clone(&manager));
         let ctx = JobContext::default();
         let result = tool
             .execute(serde_json::json!({ "job_id": job_id.to_string() }), &ctx)
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         assert_eq!(
+            /* safety: test */
             result.result.get("status").and_then(|v| v.as_str()),
             Some("Completed")
         );
-        assert!(result.result.get("started_at").unwrap().is_string());
-        assert!(result.result.get("completed_at").unwrap().is_string());
+        assert!(result.result.get("started_at").unwrap().is_string()); // safety: test
+        assert!(result.result.get("completed_at").unwrap().is_string()); // safety: test
     }
 
     #[tokio::test]
@@ -1616,26 +1625,27 @@ mod tests {
         let job_id = manager
             .create_job_for_user("default", "Running Job", "In progress")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         manager
             .update_context(job_id, |ctx| ctx.transition_to(JobState::InProgress, None))
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         let tool = CancelJobTool::new(Arc::clone(&manager));
         let ctx = JobContext::default();
         let result = tool
             .execute(serde_json::json!({ "job_id": job_id.to_string() }), &ctx)
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         assert_eq!(
+            /* safety: test */
             result.result.get("status").and_then(|v| v.as_str()),
             Some("cancelled")
         );
-        let updated = manager.get_context(job_id).await.unwrap();
-        assert_eq!(updated.state, JobState::Cancelled);
+        let updated = manager.get_context(job_id).await.unwrap(); // safety: test
+        assert_eq!(updated.state, JobState::Cancelled); // safety: test
     }
 
     #[tokio::test]
@@ -1644,39 +1654,81 @@ mod tests {
         let job_id = manager
             .create_job_for_user("default", "Completed Job", "Already done")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         manager
             .update_context(job_id, |ctx| {
                 ctx.transition_to(JobState::InProgress, None)?;
                 ctx.transition_to(JobState::Completed, Some("done".to_string()))
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         let tool = CancelJobTool::new(Arc::clone(&manager));
         let ctx = JobContext::default();
         let result = tool
             .execute(serde_json::json!({ "job_id": job_id.to_string() }), &ctx)
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
-        let error = result.result.get("error").and_then(|v| v.as_str()).unwrap();
-        assert!(error.contains("Cannot cancel job"));
-        assert!(error.contains("completed"));
+        let error = result.result.get("error").and_then(|v| v.as_str()).unwrap(); // safety: test
+        assert!(error.contains("Cannot cancel job")); // safety: test
+        assert!(error.contains("completed")); // safety: test
+    }
+
+    #[tokio::test]
+    async fn test_job_status_includes_fallback_deliverable() {
+        let manager = Arc::new(ContextManager::new(5));
+        let job_id = manager
+            .create_job_for_user("default", "Failing Job", "Will fail")
+            .await
+            .unwrap(); // safety: test
+
+        // Inject a real FallbackDeliverable into the job metadata.
+        let fallback = serde_json::json!({
+            "partial": true,
+            "failure_reason": "max iterations",
+            "last_action": null,
+            "action_stats": { "total": 5, "successful": 3, "failed": 2 },
+            "tokens_used": 1000,
+            "cost": "0.05",
+            "elapsed_secs": 12.5,
+            "repair_attempts": 1,
+        });
+        manager
+            .update_context(job_id, |ctx| {
+                ctx.metadata = serde_json::json!({ "fallback_deliverable": fallback.clone() });
+                Ok::<(), String>(())
+            })
+            .await
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
+
+        let tool = JobStatusTool::new(manager);
+        let params = serde_json::json!({ "job_id": job_id.to_string() });
+        let ctx = JobContext::default();
+        let result = tool.execute(params, &ctx).await.unwrap(); // safety: test
+
+        let fb = result.result.get("fallback_deliverable").unwrap(); // safety: test
+        assert_eq!(fb.get("partial").unwrap(), true); // safety: test
+        assert_eq!(fb.get("failure_reason").unwrap(), "max iterations"); // safety: test
+        let stats = fb.get("action_stats").unwrap(); // safety: test
+        assert_eq!(stats.get("total").unwrap(), 5); // safety: test
+        assert_eq!(stats.get("successful").unwrap(), 3); // safety: test
+        assert_eq!(stats.get("failed").unwrap(), 2); // safety: test
     }
 
     #[test]
     fn test_resolve_project_dir_auto() {
         let project_id = Uuid::new_v4();
-        let (dir, browse_id) = resolve_project_dir(None, project_id).unwrap();
-        assert!(dir.exists());
-        assert!(dir.ends_with(project_id.to_string()));
-        assert_eq!(browse_id, project_id.to_string());
+        let (dir, browse_id) = resolve_project_dir(None, project_id).unwrap(); // safety: test
+        assert!(dir.exists()); // safety: test
+        assert!(dir.ends_with(project_id.to_string())); // safety: test
+        assert_eq!(browse_id, project_id.to_string()); // safety: test
 
         // Must be under the projects base
-        let base = projects_base().canonicalize().unwrap();
-        assert!(dir.starts_with(&base));
+        let base = projects_base().canonicalize().unwrap(); // safety: test
+        assert!(dir.starts_with(&base)); // safety: test
 
         let _ = std::fs::remove_dir_all(&dir);
     }
@@ -1684,33 +1736,34 @@ mod tests {
     #[test]
     fn test_resolve_project_dir_explicit_under_base() {
         let base = projects_base();
-        std::fs::create_dir_all(&base).unwrap();
+        std::fs::create_dir_all(&base).unwrap(); // safety: test
         let explicit = base.join("test_explicit_project");
         // Explicit paths must already exist (no auto-create).
-        std::fs::create_dir_all(&explicit).unwrap();
+        std::fs::create_dir_all(&explicit).unwrap(); // safety: test
         let project_id = Uuid::new_v4();
 
-        let (dir, browse_id) = resolve_project_dir(Some(explicit.clone()), project_id).unwrap();
-        assert!(dir.exists());
-        assert_eq!(browse_id, "test_explicit_project");
+        let (dir, browse_id) = resolve_project_dir(Some(explicit.clone()), project_id).unwrap(); // safety: test
+        assert!(dir.exists()); // safety: test
+        assert_eq!(browse_id, "test_explicit_project"); // safety: test
 
-        let canonical_base = base.canonicalize().unwrap();
-        assert!(dir.starts_with(&canonical_base));
+        let canonical_base = base.canonicalize().unwrap(); // safety: test
+        assert!(dir.starts_with(&canonical_base)); // safety: test
 
         let _ = std::fs::remove_dir_all(&explicit);
     }
 
     #[test]
     fn test_resolve_project_dir_rejects_outside_base() {
-        let tmp = tempfile::tempdir().unwrap();
+        let tmp = tempfile::tempdir().unwrap(); // safety: test
         let escape_attempt = tmp.path().join("evil_project");
         // Don't create it: explicit paths that don't exist are rejected
         // before the prefix check even runs.
 
         let result = resolve_project_dir(Some(escape_attempt), Uuid::new_v4());
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("does not exist"),
             "expected 'does not exist' error, got: {}",
             err
@@ -1720,13 +1773,14 @@ mod tests {
     #[test]
     fn test_resolve_project_dir_rejects_outside_base_existing() {
         // A directory that exists but is outside the projects base.
-        let tmp = tempfile::tempdir().unwrap();
+        let tmp = tempfile::tempdir().unwrap(); // safety: test
         let outside = tmp.path().to_path_buf();
 
         let result = resolve_project_dir(Some(outside), Uuid::new_v4());
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("must be under"),
             "expected 'must be under' error, got: {}",
             err
@@ -1740,7 +1794,7 @@ mod tests {
         let traversal = base.join("legit").join("..").join("..").join(".ssh");
 
         let result = resolve_project_dir(Some(traversal), Uuid::new_v4());
-        assert!(result.is_err(), "traversal path should be rejected");
+        assert!(result.is_err(), "traversal path should be rejected"); // safety: test
 
         // Traversal path that actually resolves gets the prefix check.
         // `base/../` resolves to the parent of projects base, which is outside.
@@ -1748,7 +1802,7 @@ mod tests {
         std::fs::create_dir_all(&base_parent).ok();
         if base_parent.exists() {
             let result = resolve_project_dir(Some(base_parent.clone()), Uuid::new_v4());
-            assert!(result.is_err(), "path outside base should be rejected");
+            assert!(result.is_err(), "path outside base should be rejected"); // safety: test
             let _ = std::fs::remove_dir_all(&base_parent);
         }
     }
@@ -1762,8 +1816,9 @@ mod tests {
         ));
         let tool = CreateJobTool::new(manager).with_sandbox(jm, None);
         let schema = tool.parameters_schema();
-        let props = schema.get("properties").unwrap().as_object().unwrap();
+        let props = schema.get("properties").unwrap().as_object().unwrap(); // safety: test
         assert!(
+            /* safety: test */
             props.contains_key("project_dir"),
             "sandbox schema must expose project_dir"
         );
@@ -1778,8 +1833,9 @@ mod tests {
         ));
         let tool = CreateJobTool::new(manager).with_sandbox(jm, None);
         let schema = tool.parameters_schema();
-        let props = schema.get("properties").unwrap().as_object().unwrap();
+        let props = schema.get("properties").unwrap().as_object().unwrap(); // safety: test
         assert!(
+            /* safety: test */
             props.contains_key("credentials"),
             "sandbox schema must expose credentials"
         );
@@ -1792,13 +1848,13 @@ mod tests {
 
         // No credentials parameter
         let params = serde_json::json!({"title": "t", "description": "d"});
-        let grants = tool.parse_credentials(&params, "user1").await.unwrap();
-        assert!(grants.is_empty());
+        let grants = tool.parse_credentials(&params, "user1").await.unwrap(); // safety: test
+        assert!(grants.is_empty()); // safety: test
 
         // Empty credentials object
         let params = serde_json::json!({"credentials": {}});
-        let grants = tool.parse_credentials(&params, "user1").await.unwrap();
-        assert!(grants.is_empty());
+        let grants = tool.parse_credentials(&params, "user1").await.unwrap(); // safety: test
+        assert!(grants.is_empty()); // safety: test
     }
 
     #[tokio::test]
@@ -1808,9 +1864,10 @@ mod tests {
 
         let params = serde_json::json!({"credentials": {"my_secret": "MY_SECRET"}});
         let result = tool.parse_credentials(&params, "user1").await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("no secrets store"),
             "expected 'no secrets store' error, got: {}",
             err
@@ -1828,9 +1885,10 @@ mod tests {
 
         let params = serde_json::json!({"credentials": {"nonexistent_secret": "SOME_VAR"}});
         let result = tool.parse_credentials(&params, "user1").await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("not found"),
             "expected 'not found' error, got: {}",
             err
@@ -1852,17 +1910,17 @@ mod tests {
                 CreateSecretParams::new("github_token", TEST_GITHUB_TOKEN),
             )
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         let tool = CreateJobTool::new(manager).with_secrets(Arc::clone(&secrets));
 
         let params = serde_json::json!({
             "credentials": {"github_token": "GITHUB_TOKEN"}
         });
-        let grants = tool.parse_credentials(&params, "user1").await.unwrap();
-        assert_eq!(grants.len(), 1);
-        assert_eq!(grants[0].secret_name, "github_token");
-        assert_eq!(grants[0].env_var, "GITHUB_TOKEN");
+        let grants = tool.parse_credentials(&params, "user1").await.unwrap(); // safety: test
+        assert_eq!(grants.len(), 1); // safety: test
+        assert_eq!(grants[0].secret_name, "github_token"); // safety: test
+        assert_eq!(grants[0].env_var, "GITHUB_TOKEN"); // safety: test
     }
 
     fn test_prompt_tool(queue: PromptQueue) -> JobPromptTool {
@@ -1876,7 +1934,7 @@ mod tests {
         let job_id = cm
             .create_job_for_user("default", "Test Job", "desc")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         let queue: PromptQueue =
             Arc::new(tokio::sync::Mutex::new(std::collections::HashMap::new()));
@@ -1889,18 +1947,19 @@ mod tests {
         });
 
         let ctx = JobContext::default();
-        let result = tool.execute(params, &ctx).await.unwrap();
+        let result = tool.execute(params, &ctx).await.unwrap(); // safety: test
 
         assert_eq!(
-            result.result.get("status").unwrap().as_str().unwrap(),
+            /* safety: test */
+            result.result.get("status").unwrap().as_str().unwrap(), // safety: test
             "queued"
         );
 
         let q = queue.lock().await;
-        let prompts = q.get(&job_id).unwrap();
-        assert_eq!(prompts.len(), 1);
-        assert_eq!(prompts[0].content, "What's the status?");
-        assert!(!prompts[0].done);
+        let prompts = q.get(&job_id).unwrap(); // safety: test
+        assert_eq!(prompts.len(), 1); // safety: test
+        assert_eq!(prompts[0].content, "What's the status?"); // safety: test
+        assert!(!prompts[0].done); // safety: test
     }
 
     #[tokio::test]
@@ -1910,6 +1969,7 @@ mod tests {
             Arc::new(tokio::sync::Mutex::new(std::collections::HashMap::new()));
         let tool = test_prompt_tool(queue);
         assert_eq!(
+            /* safety: test */
             tool.requires_approval(&serde_json::json!({})),
             ApprovalRequirement::UnlessAutoApproved
         );
@@ -1928,7 +1988,7 @@ mod tests {
 
         let ctx = JobContext::default();
         let result = tool.execute(params, &ctx).await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
     }
 
     #[tokio::test]
@@ -1943,7 +2003,7 @@ mod tests {
 
         let ctx = JobContext::default();
         let result = tool.execute(params, &ctx).await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
     }
 
     #[tokio::test]
@@ -1958,7 +2018,7 @@ mod tests {
         let job_id = cm
             .create_job_for_user("owner-user", "Secret Job", "classified")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         // We need a Store to construct the tool, but creating one requires
         // a database URL. Instead, test the ownership logic directly:
@@ -1968,9 +2028,9 @@ mod tests {
             ..Default::default()
         };
 
-        let job_ctx = cm.get_context(job_id).await.unwrap();
-        assert_ne!(job_ctx.user_id, attacker_ctx.user_id);
-        assert_eq!(job_ctx.user_id, "owner-user");
+        let job_ctx = cm.get_context(job_id).await.unwrap(); // safety: test
+        assert_ne!(job_ctx.user_id, attacker_ctx.user_id); // safety: test
+        assert_eq!(job_ctx.user_id, "owner-user"); // safety: test
     }
 
     #[test]
@@ -1991,12 +2051,12 @@ mod tests {
             "required": ["job_id"]
         });
 
-        let props = schema.get("properties").unwrap().as_object().unwrap();
-        assert!(props.contains_key("job_id"));
-        assert!(props.contains_key("limit"));
-        let required = schema.get("required").unwrap().as_array().unwrap();
-        assert_eq!(required.len(), 1);
-        assert_eq!(required[0].as_str().unwrap(), "job_id");
+        let props = schema.get("properties").unwrap().as_object().unwrap(); // safety: test
+        assert!(props.contains_key("job_id")); // safety: test
+        assert!(props.contains_key("limit")); // safety: test
+        let required = schema.get("required").unwrap().as_array().unwrap(); // safety: test
+        assert_eq!(required.len(), 1); // safety: test
+        assert_eq!(required[0].as_str().unwrap(), "job_id"); // safety: test
     }
 
     #[tokio::test]
@@ -2005,7 +2065,7 @@ mod tests {
         let job_id = cm
             .create_job_for_user("owner-user", "Test Job", "desc")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         let queue: PromptQueue =
             Arc::new(tokio::sync::Mutex::new(std::collections::HashMap::new()));
@@ -2023,9 +2083,10 @@ mod tests {
         };
 
         let result = tool.execute(params, &ctx).await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("does not belong to current user"),
             "expected ownership error, got: {}",
             err
@@ -2035,33 +2096,34 @@ mod tests {
     #[tokio::test]
     async fn test_resolve_job_id_full_uuid() {
         let cm = ContextManager::new(5);
-        let job_id = cm.create_job("Test", "Desc").await.unwrap();
+        let job_id = cm.create_job("Test", "Desc").await.unwrap(); // safety: test
 
-        let resolved = resolve_job_id(&job_id.to_string(), &cm).await.unwrap();
-        assert_eq!(resolved, job_id);
+        let resolved = resolve_job_id(&job_id.to_string(), &cm).await.unwrap(); // safety: test
+        assert_eq!(resolved, job_id); // safety: test
     }
 
     #[tokio::test]
     async fn test_resolve_job_id_short_prefix() {
         let cm = ContextManager::new(5);
-        let job_id = cm.create_job("Test", "Desc").await.unwrap();
+        let job_id = cm.create_job("Test", "Desc").await.unwrap(); // safety: test
 
         // Use first 8 hex chars (without dashes)
         let hex = job_id.to_string().replace('-', "");
         let prefix = &hex[..8];
-        let resolved = resolve_job_id(prefix, &cm).await.unwrap();
-        assert_eq!(resolved, job_id);
+        let resolved = resolve_job_id(prefix, &cm).await.unwrap(); // safety: test
+        assert_eq!(resolved, job_id); // safety: test
     }
 
     #[tokio::test]
     async fn test_resolve_job_id_no_match() {
         let cm = ContextManager::new(5);
-        cm.create_job("Test", "Desc").await.unwrap();
+        cm.create_job("Test", "Desc").await.unwrap(); // safety: test
 
         let result = resolve_job_id("00000000", &cm).await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
         let err = result.unwrap_err().to_string();
         assert!(
+            /* safety: test */
             err.contains("no job found"),
             "expected 'no job found', got: {}",
             err
@@ -2072,6 +2134,6 @@ mod tests {
     async fn test_resolve_job_id_invalid_input() {
         let cm = ContextManager::new(5);
         let result = resolve_job_id("not-hex-at-all!", &cm).await;
-        assert!(result.is_err());
+        assert!(result.is_err()); // safety: test
     }
 }

src/worker/job.rs

@@ -196,6 +196,7 @@ impl Worker {
                         .get("session_id")
                         .and_then(|v| v.as_str())
                         .map(|s| s.to_string()),
+                    fallback_deliverable: data.get("fallback_deliverable").cloned(),
                 }),
                 _ => None,
             };
@@ -960,9 +961,14 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
     }
 
     async fn mark_failed(&self, reason: &str) -> Result<(), Error> {
+        // Build fallback deliverable from memory before transitioning.
+        let fallback = self.build_fallback(reason).await;
+
         self.context_manager()
             .update_context(self.job_id, |ctx| {
-                ctx.transition_to(JobState::Failed, Some(reason.to_string()))
+                ctx.transition_to(JobState::Failed, Some(reason.to_string()))?;
+                store_fallback_in_metadata(ctx, fallback.as_ref());
+                Ok(())
             })
             .await?
             .map_err(|s| crate::error::JobError::ContextError {
@@ -983,8 +989,15 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
     }
 
     async fn mark_stuck(&self, reason: &str) -> Result<(), Error> {
+        // Build fallback deliverable from memory before transitioning.
+        let fallback = self.build_fallback(reason).await;
+
         self.context_manager()
-            .update_context(self.job_id, |ctx| ctx.mark_stuck(reason))
+            .update_context(self.job_id, |ctx| {
+                ctx.mark_stuck(reason)?;
+                store_fallback_in_metadata(ctx, fallback.as_ref());
+                Ok(())
+            })
             .await?
             .map_err(|s| crate::error::JobError::ContextError {
                 id: self.job_id,
@@ -1002,6 +1015,57 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
         self.persist_status(JobState::Stuck, Some(reason.to_string()));
         Ok(())
     }
+
+    /// Build a [`FallbackDeliverable`] from the current job context and memory.
+    async fn build_fallback(&self, reason: &str) -> Option<crate::context::FallbackDeliverable> {
+        let memory = match self.context_manager().get_memory(self.job_id).await {
+            Ok(memory) => memory,
+            Err(e) => {
+                tracing::warn!(
+                    job_id = %self.job_id,
+                    "Failed to load memory while building fallback deliverable: {e}"
+                );
+                return None;
+            }
+        };
+        let ctx = match self.context_manager().get_context(self.job_id).await {
+            Ok(ctx) => ctx,
+            Err(e) => {
+                tracing::warn!(
+                    job_id = %self.job_id,
+                    "Failed to load context while building fallback deliverable: {e}"
+                );
+                return None;
+            }
+        };
+        Some(crate::context::FallbackDeliverable::build(
+            &ctx, &memory, reason,
+        ))
+    }
+}
+
+/// Store a fallback deliverable in the job context's metadata.
+fn store_fallback_in_metadata(
+    ctx: &mut crate::context::JobContext,
+    fallback: Option<&crate::context::FallbackDeliverable>,
+) {
+    let Some(fb) = fallback else {
+        return;
+    };
+    match serde_json::to_value(fb) {
+        Ok(val) => {
+            if !ctx.metadata.is_object() {
+                ctx.metadata = serde_json::json!({});
+            }
+            ctx.metadata["fallback_deliverable"] = val;
+        }
+        Err(e) => {
+            tracing::warn!(
+                "Failed to serialize fallback deliverable for job {}: {e}",
+                ctx.job_id
+            );
+        }
+    }
 }
 
 /// Job delegate: implements `LoopDelegate` for the background job context.
@@ -1440,7 +1504,7 @@ mod tests {
         }
 
         let cm = Arc::new(crate::context::ContextManager::new(5));
-        let job_id = cm.create_job("test", "test job").await.unwrap();
+        let job_id = cm.create_job("test", "test job").await.unwrap(); // safety: test
 
         let deps = WorkerDeps {
             context_manager: cm,
@@ -1472,8 +1536,9 @@ mod tests {
             tool_call_id: "call_abc123".to_string(),
         };
 
-        assert_eq!(selection.tool_call_id, "call_abc123");
+        assert_eq!(selection.tool_call_id, "call_abc123"); // safety: test
         assert_ne!(
+            /* safety: test */
             selection.tool_call_id, "tool_call_id",
             "tool_call_id must not be the hardcoded placeholder string"
         );
@@ -1509,11 +1574,12 @@ mod tests {
         let results = worker.execute_tools_parallel(&selections).await;
         let elapsed = start.elapsed();
 
-        assert_eq!(results.len(), 3);
+        assert_eq!(results.len(), 3); // safety: test
         for r in &results {
-            assert!(r.result.is_ok(), "Tool should succeed");
+            assert!(r.result.is_ok(), "Tool should succeed"); // safety: test
         }
         assert!(
+            /* safety: test */
             elapsed < Duration::from_millis(800),
             "Parallel execution took {:?}, expected < 800ms (sequential would be ~600ms)",
             elapsed
@@ -1565,9 +1631,9 @@ mod tests {
 
         let results = worker.execute_tools_parallel(&selections).await;
 
-        assert!(results[0].result.as_ref().unwrap().contains("done_tool_a"));
-        assert!(results[1].result.as_ref().unwrap().contains("done_tool_b"));
-        assert!(results[2].result.as_ref().unwrap().contains("done_tool_c"));
+        assert!(results[0].result.as_ref().unwrap().contains("done_tool_a")); // safety: test
+        assert!(results[1].result.as_ref().unwrap().contains("done_tool_b")); // safety: test
+        assert!(results[2].result.as_ref().unwrap().contains("done_tool_c")); // safety: test
     }
 
     #[tokio::test]
@@ -1583,8 +1649,9 @@ mod tests {
         }];
 
         let results = worker.execute_tools_parallel(&selections).await;
-        assert_eq!(results.len(), 1);
+        assert_eq!(results.len(), 1); // safety: test
         assert!(
+            /* safety: test */
             results[0].result.is_err(),
             "Missing tool should produce an error, not a panic"
         );
@@ -1600,23 +1667,24 @@ mod tests {
                 ctx.transition_to(JobState::InProgress, None)
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
-        worker.mark_completed().await.unwrap();
+        worker.mark_completed().await.unwrap(); // safety: test
 
         let ctx = worker
             .context_manager()
             .get_context(worker.job_id)
             .await
-            .unwrap();
-        assert_eq!(ctx.state, JobState::Completed);
+            .unwrap(); // safety: test
+        assert_eq!(ctx.state, JobState::Completed); // safety: test
 
         // Second mark_completed should succeed (idempotent) rather than
         // erroring, matching the fix for the execution_loop / worker wrapper
         // race condition.
         let result = worker.mark_completed().await;
         assert!(
+            /* safety: test */
             result.is_ok(),
             "Completed -> Completed transition should be idempotent"
         );
@@ -1641,7 +1709,7 @@ mod tests {
         }
 
         let cm = Arc::new(crate::context::ContextManager::new(5));
-        let job_id = cm.create_job("test", "test job").await.unwrap();
+        let job_id = cm.create_job("test", "test job").await.unwrap(); // safety: test
 
         let deps = WorkerDeps {
             context_manager: cm,
@@ -1740,6 +1808,7 @@ mod tests {
             .execute_tool("needs_approval", &serde_json::json!({}))
             .await;
         assert!(
+            /* safety: test */
             result.is_err(),
             "Should be blocked without approval context"
         );
@@ -1752,7 +1821,7 @@ mod tests {
         let result = worker_allowed
             .execute_tool("needs_approval", &serde_json::json!({}))
             .await;
-        assert!(result.is_ok(), "Should be allowed with autonomous context");
+        assert!(result.is_ok(), "Should be allowed with autonomous context"); // safety: test
     }
 
     #[tokio::test]
@@ -1766,6 +1835,7 @@ mod tests {
             .execute_tool("always_approval", &serde_json::json!({}))
             .await;
         assert!(
+            /* safety: test */
             result.is_err(),
             "Always tool should be blocked without permission"
         );
@@ -1781,6 +1851,7 @@ mod tests {
             .execute_tool("always_approval", &serde_json::json!({}))
             .await;
         assert!(
+            /* safety: test */
             result.is_ok(),
             "Always tool should be allowed with permission"
         );
@@ -1797,8 +1868,8 @@ mod tests {
                 ctx.transition_to(JobState::InProgress, None)
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         // Set a token budget
         worker
@@ -1807,16 +1878,17 @@ mod tests {
                 ctx.max_tokens = 100;
             })
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         // Simulate adding tokens that exceed the budget
         let budget_result = worker
             .context_manager()
             .update_context(worker.job_id, |ctx| ctx.add_tokens(200))
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         assert!(
+            /* safety: test */
             budget_result.is_err(),
             "Should return error when token budget exceeded"
         );
@@ -1825,13 +1897,13 @@ mod tests {
         worker
             .mark_failed(&budget_result.unwrap_err().to_string())
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         let ctx = worker
             .context_manager()
             .get_context(worker.job_id)
             .await
-            .unwrap();
-        assert_eq!(ctx.state, JobState::Failed);
+            .unwrap(); // safety: test
+        assert_eq!(ctx.state, JobState::Failed); // safety: test
     }
 
     #[tokio::test]
@@ -1845,21 +1917,22 @@ mod tests {
                 ctx.transition_to(JobState::InProgress, None)
             })
             .await
-            .unwrap()
-            .unwrap();
+            .unwrap() // safety: test
+            .unwrap(); // safety: test
 
         // Simulate what the execution loop does when max_iterations is exceeded
         worker
             .mark_failed("Maximum iterations exceeded: job hit the iteration cap")
             .await
-            .unwrap();
+            .unwrap(); // safety: test
 
         let ctx = worker
             .context_manager()
             .get_context(worker.job_id)
             .await
-            .unwrap();
+            .unwrap(); // safety: test
         assert_eq!(
+            /* safety: test */
             ctx.state,
             JobState::Failed,
             "Iteration cap should transition to Failed, not Stuck"
@@ -1989,4 +2062,52 @@ mod tests {
             "Should skip empty first reasoning and return the first non-empty one"
         );
     }
+
+    #[test]
+    fn test_store_fallback_in_metadata_roundtrip() {
+        use crate::context::FallbackDeliverable;
+
+        let mut ctx = JobContext::new("Test", "fallback roundtrip");
+        let memory = crate::context::Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "test failure");
+
+        // Store into metadata
+        store_fallback_in_metadata(&mut ctx, Some(&fb));
+
+        // Verify it's stored and can be deserialized back
+        let stored = ctx.metadata.get("fallback_deliverable");
+        assert!(stored.is_some(), "fallback missing from metadata"); // safety: test
+
+        let recovered: FallbackDeliverable =
+            serde_json::from_value(stored.unwrap().clone()).expect("deserialize fallback"); // safety: test
+        assert_eq!(recovered.failure_reason, "test failure"); // safety: test
+        assert!(!recovered.partial); // safety: test
+    }
+
+    #[test]
+    fn test_store_fallback_handles_non_object_metadata() {
+        use crate::context::FallbackDeliverable;
+
+        let mut ctx = JobContext::new("Test", "non-object metadata");
+        ctx.metadata = serde_json::json!("not an object");
+
+        let memory = crate::context::Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+
+        store_fallback_in_metadata(&mut ctx, Some(&fb));
+
+        // Must normalize to object and store
+        assert!(ctx.metadata.is_object()); // safety: test
+        assert!(ctx.metadata.get("fallback_deliverable").is_some()); // safety: test
+    }
+
+    #[test]
+    fn test_store_fallback_none_is_noop() {
+        let mut ctx = JobContext::new("Test", "noop");
+        let original = ctx.metadata.clone();
+
+        store_fallback_in_metadata(&mut ctx, None);
+
+        assert_eq!(ctx.metadata, original); // safety: test
+    }
 }

src/workspace/README.md

@@ -38,12 +38,17 @@ workspace/
 ## Using the Workspace
 
 ```rust
+use std::sync::Arc;
 use crate::workspace::{Workspace, OpenAiEmbeddings, paths};
 
-// Create workspace for a user
+// Create workspace for a user (wraps embeddings in a default LRU cache)
 let workspace = Workspace::new("user_123", pool)
     .with_embeddings(Arc::new(OpenAiEmbeddings::new(api_key)));
 
+// For tests: skip the cache layer (avoids unnecessary overhead with mocks)
+// let workspace = Workspace::new("user_123", pool)
+//     .with_embeddings_uncached(Arc::new(MockEmbeddings::new(1536)));
+
 // Read/write any path
 let doc = workspace.read("projects/alpha/notes.md").await?;
 workspace.write("context/priorities.md", "# Priorities\n\n1. Feature X").await?;

src/workspace/embedding_cache.rs

@@ -0,0 +1,613 @@
+//! LRU embedding cache wrapping any [`EmbeddingProvider`].
+//!
+//! 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.
+
+use std::collections::HashMap;
+use std::sync::{Arc, Mutex};
+use std::time::Instant;
+
+use async_trait::async_trait;
+use sha2::{Digest, Sha256};
+
+use crate::workspace::embeddings::{EmbeddingError, EmbeddingProvider};
+
+/// Configuration for the embedding cache.
+#[derive(Debug, Clone)]
+pub struct EmbeddingCacheConfig {
+    /// Maximum number of cached embeddings (default 10,000).
+    ///
+    /// 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).
+    pub max_entries: usize,
+}
+
+impl Default for EmbeddingCacheConfig {
+    fn default() -> Self {
+        Self {
+            max_entries: crate::config::DEFAULT_EMBEDDING_CACHE_SIZE,
+        }
+    }
+}
+
+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**
+/// across `.await` points (all critical sections are scoped blocks),
+/// 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,
+}
+
+impl CachedEmbeddingProvider {
+    /// Wrap a provider with LRU caching.
+    ///
+    /// `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 {
+            tracing::warn!(
+                max_entries = config.max_entries,
+                "Embedding cache size exceeds 100,000 entries; memory usage may be significant"
+            );
+        }
+        Self {
+            inner,
+            cache: Mutex::new(HashMap::with_capacity(config.max_entries.min(1024))),
+            config,
+        }
+    }
+
+    /// Number of entries currently in the cache.
+    pub fn len(&self) -> usize {
+        self.cache.lock().unwrap_or_else(|e| e.into_inner()).len()
+    }
+
+    /// Whether the cache is empty.
+    pub fn is_empty(&self) -> bool {
+        self.cache
+            .lock()
+            .unwrap_or_else(|e| e.into_inner())
+            .is_empty()
+    }
+
+    /// Clear all cached entries.
+    pub fn clear(&self) {
+        self.cache.lock().unwrap_or_else(|e| e.into_inner()).clear();
+    }
+
+    /// Build a deterministic cache key: `SHA-256(model_name + "\0" + text)`.
+    ///
+    /// Returns raw 32-byte hash to avoid a 64-char hex String allocation per lookup.
+    fn cache_key(&self, text: &str) -> [u8; 32] {
+        let mut hasher = Sha256::new();
+        hasher.update(self.inner.model_name().as_bytes());
+        hasher.update(b"\0");
+        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]
+impl EmbeddingProvider for CachedEmbeddingProvider {
+    fn dimension(&self) -> usize {
+        self.inner.dimension()
+    }
+
+    fn model_name(&self) -> &str {
+        self.inner.model_name()
+    }
+
+    fn max_input_length(&self) -> usize {
+        self.inner.max_input_length()
+    }
+
+    async fn embed(&self, text: &str) -> Result<Vec<f32>, EmbeddingError> {
+        let key = self.cache_key(text);
+
+        // Check cache (short critical section)
+        {
+            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();
+                tracing::trace!("embedding cache hit");
+                return Ok(entry.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.
+
+        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.
+        {
+            let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
+            if let Some(entry) = guard.get_mut(&key) {
+                // Key already present (thundering herd) — just update, no eviction needed.
+                entry.embedding = embedding.clone();
+                entry.last_accessed = Instant::now();
+            } else {
+                Self::evict_lru(&mut guard, self.config.max_entries);
+                guard.insert(
+                    key,
+                    CacheEntry {
+                        embedding: embedding.clone(),
+                        last_accessed: Instant::now(),
+                    },
+                );
+            }
+        }
+
+        tracing::trace!("embedding cache miss");
+        Ok(embedding)
+    }
+
+    async fn embed_batch(&self, texts: &[String]) -> Result<Vec<Vec<f32>>, EmbeddingError> {
+        if texts.is_empty() {
+            return Ok(Vec::new());
+        }
+
+        // Partition into hits and misses
+        let keys: Vec<[u8; 32]> = texts.iter().map(|t| self.cache_key(t)).collect();
+        let mut results: Vec<Option<Vec<f32>>> = vec![None; texts.len()];
+        let mut miss_indices: Vec<usize> = Vec::new();
+
+        {
+            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());
+                } else {
+                    miss_indices.push(i);
+                }
+            }
+        }
+        // Lock released before HTTP call
+
+        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()
+                .map(|(i, slot)| {
+                    slot.ok_or_else(|| {
+                        EmbeddingError::InvalidResponse(format!(
+                            "embedding slot {i} was not populated"
+                        ))
+                    })
+                })
+                .collect::<Result<Vec<_>, _>>();
+        }
+
+        // Fetch missing embeddings
+        let miss_texts: Vec<String> = miss_indices.iter().map(|&i| texts[i].clone()).collect();
+        let new_embeddings = self.inner.embed_batch(&miss_texts).await?;
+
+        if new_embeddings.len() != miss_indices.len() {
+            return Err(EmbeddingError::InvalidResponse(format!(
+                "embed_batch returned {} embeddings, expected {}",
+                new_embeddings.len(),
+                miss_indices.len()
+            )));
+        }
+
+        tracing::trace!(
+            hits = texts.len() - miss_indices.len(),
+            misses = miss_indices.len(),
+            "embedding batch: partial cache"
+        );
+
+        // Assemble results first (all misses, regardless of cache capacity).
+        for (orig_idx, emb) in miss_indices.iter().copied().zip(&new_embeddings) {
+            results[orig_idx] = Some(emb.clone());
+        }
+
+        // Cache the new embeddings, respecting max_entries.
+        {
+            let mut guard = self.cache.lock().unwrap_or_else(|e| e.into_inner());
+            // When misses exceed capacity, clear and only cache the tail.
+            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();
+            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,
+                    },
+                );
+            }
+        }
+
+        results
+            .into_iter()
+            .enumerate()
+            .map(|(i, slot)| {
+                slot.ok_or_else(|| {
+                    EmbeddingError::InvalidResponse(format!("embedding slot {i} was not populated"))
+                })
+            })
+            .collect()
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use std::sync::atomic::{AtomicU32, Ordering};
+
+    /// Mock embedding provider that counts calls.
+    struct CountingMock {
+        dimension: usize,
+        model: String,
+        embed_calls: AtomicU32,
+        batch_calls: AtomicU32,
+    }
+
+    impl CountingMock {
+        fn new(dimension: usize, model: &str) -> Self {
+            Self {
+                dimension,
+                model: model.to_string(),
+                embed_calls: AtomicU32::new(0),
+                batch_calls: AtomicU32::new(0),
+            }
+        }
+
+        fn embed_calls(&self) -> u32 {
+            self.embed_calls.load(Ordering::SeqCst)
+        }
+
+        fn batch_calls(&self) -> u32 {
+            self.batch_calls.load(Ordering::SeqCst)
+        }
+    }
+
+    #[async_trait]
+    impl EmbeddingProvider for CountingMock {
+        fn dimension(&self) -> usize {
+            self.dimension
+        }
+        fn model_name(&self) -> &str {
+            &self.model
+        }
+        fn max_input_length(&self) -> usize {
+            10_000
+        }
+        async fn embed(&self, text: &str) -> Result<Vec<f32>, EmbeddingError> {
+            self.embed_calls.fetch_add(1, Ordering::SeqCst);
+            // Simple deterministic embedding: val = text.len() / 100.0
+            let val = text.len() as f32 / 100.0;
+            Ok(vec![val; self.dimension])
+        }
+        async fn embed_batch(&self, texts: &[String]) -> Result<Vec<Vec<f32>>, EmbeddingError> {
+            self.batch_calls.fetch_add(1, Ordering::SeqCst);
+            texts
+                .iter()
+                .map(|t| {
+                    let val = t.len() as f32 / 100.0;
+                    Ok(vec![val; self.dimension])
+                })
+                .collect()
+        }
+    }
+
+    #[tokio::test]
+    async fn cache_hit_avoids_inner_call() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        let r1 = cached.embed("hello").await.unwrap();
+        assert_eq!(inner.embed_calls(), 1);
+
+        let r2 = cached.embed("hello").await.unwrap();
+        assert_eq!(inner.embed_calls(), 1); // still 1 -- cache hit
+        assert_eq!(r1, r2);
+
+        assert_eq!(cached.len(), 1);
+    }
+
+    #[tokio::test]
+    async fn cache_miss_calls_inner() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        cached.embed("hello").await.unwrap();
+        cached.embed("world").await.unwrap();
+        assert_eq!(inner.embed_calls(), 2);
+        assert_eq!(cached.len(), 2);
+    }
+
+    #[tokio::test]
+    async fn cache_key_includes_model() {
+        let inner_a = Arc::new(CountingMock::new(4, "model-a"));
+        let inner_b = Arc::new(CountingMock::new(4, "model-b"));
+
+        let cached_a = CachedEmbeddingProvider::new(
+            inner_a.clone(),
+            EmbeddingCacheConfig { max_entries: 100 },
+        );
+        let cached_b = CachedEmbeddingProvider::new(
+            inner_b.clone(),
+            EmbeddingCacheConfig { max_entries: 100 },
+        );
+
+        // Same text, different models -> different cache keys
+        let key_a = cached_a.cache_key("hello");
+        let key_b = cached_b.cache_key("hello");
+        assert_ne!(key_a, key_b);
+    }
+
+    #[tokio::test]
+    async fn lru_eviction() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 2 });
+
+        cached.embed("first").await.unwrap();
+        cached.embed("second").await.unwrap();
+        assert_eq!(cached.len(), 2);
+
+        // Third entry should evict the oldest ("first")
+        cached.embed("third").await.unwrap();
+        assert_eq!(cached.len(), 2);
+        assert_eq!(inner.embed_calls(), 3);
+
+        // "first" should be a cache miss now
+        cached.embed("first").await.unwrap();
+        assert_eq!(inner.embed_calls(), 4);
+    }
+
+    #[tokio::test]
+    async fn embed_batch_partial_hits() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        // Pre-cache one text
+        cached.embed("cached").await.unwrap();
+        assert_eq!(inner.embed_calls(), 1);
+
+        // Batch with 1 cached + 2 new
+        let texts = vec![
+            "cached".to_string(),
+            "new_one".to_string(),
+            "new_two".to_string(),
+        ];
+        let results = cached.embed_batch(&texts).await.unwrap();
+
+        // Should have called embed_batch on inner for 2 misses
+        assert_eq!(inner.batch_calls(), 1);
+        assert_eq!(results.len(), 3);
+        assert_eq!(cached.len(), 3);
+    }
+
+    #[tokio::test]
+    async fn batch_preserves_order() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        // Pre-cache "bb" (len 2)
+        cached.embed("bb").await.unwrap();
+
+        // Batch: "a" (miss, len 1), "bb" (hit, len 2), "ccc" (miss, len 3)
+        let texts = vec!["a".to_string(), "bb".to_string(), "ccc".to_string()];
+        let results = cached.embed_batch(&texts).await.unwrap();
+
+        assert_eq!(results.len(), 3);
+        let expected_a = vec![1.0_f32 / 100.0; 4];
+        let expected_bb = vec![2.0_f32 / 100.0; 4];
+        let expected_ccc = vec![3.0_f32 / 100.0; 4];
+        assert_eq!(results[0], expected_a);
+        assert_eq!(results[1], expected_bb);
+        assert_eq!(results[2], expected_ccc);
+    }
+
+    #[tokio::test]
+    async fn batch_exceeding_capacity_respects_max_entries() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 3 });
+
+        // Batch with 5 misses but cache capacity is 3
+        let texts: Vec<String> = (0..5).map(|i| format!("text_{i}")).collect();
+        let results = cached.embed_batch(&texts).await.unwrap();
+
+        assert_eq!(results.len(), 5);
+        let len = cached.len();
+        assert!(len <= 3, "cache len {len} exceeds max 3");
+    }
+
+    /// Mock embedding provider that fails the first N calls, then succeeds.
+    struct FailThenSucceedMock {
+        dimension: usize,
+        model: String,
+        remaining_failures: AtomicU32,
+    }
+
+    impl FailThenSucceedMock {
+        fn new(dimension: usize, fail_count: u32) -> Self {
+            Self {
+                dimension,
+                model: "fail-mock".to_string(),
+                remaining_failures: AtomicU32::new(fail_count),
+            }
+        }
+    }
+
+    #[async_trait]
+    impl EmbeddingProvider for FailThenSucceedMock {
+        fn dimension(&self) -> usize {
+            self.dimension
+        }
+        fn model_name(&self) -> &str {
+            &self.model
+        }
+        fn max_input_length(&self) -> usize {
+            10_000
+        }
+        async fn embed(&self, text: &str) -> Result<Vec<f32>, EmbeddingError> {
+            let prev =
+                self.remaining_failures
+                    .fetch_update(Ordering::SeqCst, Ordering::SeqCst, |v| {
+                        if v > 0 { Some(v - 1) } else { None }
+                    });
+            if prev.is_ok() {
+                return Err(EmbeddingError::HttpError("simulated failure".to_string()));
+            }
+            let val = text.len() as f32 / 100.0;
+            Ok(vec![val; self.dimension])
+        }
+        async fn embed_batch(&self, texts: &[String]) -> Result<Vec<Vec<f32>>, EmbeddingError> {
+            let prev =
+                self.remaining_failures
+                    .fetch_update(Ordering::SeqCst, Ordering::SeqCst, |v| {
+                        if v > 0 { Some(v - 1) } else { None }
+                    });
+            if prev.is_ok() {
+                return Err(EmbeddingError::HttpError("simulated failure".to_string()));
+            }
+            texts
+                .iter()
+                .map(|t| {
+                    let val = t.len() as f32 / 100.0;
+                    Ok(vec![val; self.dimension])
+                })
+                .collect()
+        }
+    }
+
+    #[tokio::test]
+    async fn error_does_not_pollute_cache() {
+        let inner = Arc::new(FailThenSucceedMock::new(4, 1));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        // First call fails
+        let err = cached.embed("hello").await;
+        assert!(err.is_err());
+        assert!(cached.is_empty(), "cache should be empty after error");
+
+        // Second call succeeds and should call the inner provider (not serve stale error)
+        let result = cached.embed("hello").await;
+        assert!(result.is_ok());
+        assert_eq!(cached.len(), 1);
+    }
+
+    #[tokio::test]
+    async fn embed_batch_empty_input() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        let results = cached.embed_batch(&[]).await.unwrap();
+        assert!(results.is_empty());
+        assert_eq!(inner.batch_calls(), 0);
+    }
+
+    #[tokio::test]
+    async fn embed_batch_all_misses() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 100 });
+
+        // Nothing cached — every text is a miss
+        let texts: Vec<String> = vec!["alpha".into(), "beta".into(), "gamma".into()];
+        let results = cached.embed_batch(&texts).await.unwrap();
+        assert_eq!(results.len(), 3);
+        assert_eq!(inner.batch_calls(), 1, "inner called once for misses");
+        assert_eq!(cached.len(), 3, "all results should be cached");
+
+        // Second call should be all hits — no new inner calls
+        let results2 = cached.embed_batch(&texts).await.unwrap();
+        assert_eq!(results2.len(), 3);
+        assert_eq!(inner.batch_calls(), 1, "no new inner calls");
+    }
+
+    #[tokio::test]
+    async fn zero_max_entries_clamped_to_one() {
+        let inner = Arc::new(CountingMock::new(4, "test-model"));
+        let cached =
+            CachedEmbeddingProvider::new(inner.clone(), EmbeddingCacheConfig { max_entries: 0 });
+
+        // Should behave as max_entries=1 (clamped in constructor)
+        cached.embed("hello").await.unwrap();
+        assert_eq!(cached.len(), 1);
+
+        // Second entry evicts the first
+        cached.embed("world").await.unwrap();
+        assert_eq!(cached.len(), 1);
+        assert_eq!(inner.embed_calls(), 2);
+    }
+}

src/workspace/mod.rs

@@ -42,6 +42,7 @@
 
 mod chunker;
 mod document;
+mod embedding_cache;
 mod embeddings;
 pub mod hygiene;
 #[cfg(feature = "postgres")]
@@ -50,6 +51,7 @@ mod search;
 
 pub use chunker::{ChunkConfig, chunk_document};
 pub use document::{MemoryChunk, MemoryDocument, WorkspaceEntry, paths};
+pub use embedding_cache::{CachedEmbeddingProvider, EmbeddingCacheConfig};
 pub use embeddings::{
     EmbeddingProvider, MockEmbeddings, NearAiEmbeddings, OllamaEmbeddings, OpenAiEmbeddings,
 };
@@ -371,7 +373,33 @@ impl Workspace {
     }
 
     /// Set the embedding provider for semantic search.
+    ///
+    /// The provider is automatically wrapped in a [`CachedEmbeddingProvider`]
+    /// with the default cache size (10,000 entries; payload ~58 MB for 1536-dim,
+    /// actual memory higher due to per-entry overhead).
     pub fn with_embeddings(mut self, provider: Arc<dyn EmbeddingProvider>) -> Self {
+        self.embeddings = Some(Arc::new(CachedEmbeddingProvider::new(
+            provider,
+            EmbeddingCacheConfig::default(),
+        )));
+        self
+    }
+
+    /// Set the embedding provider with a custom cache configuration.
+    pub fn with_embeddings_cached(
+        mut self,
+        provider: Arc<dyn EmbeddingProvider>,
+        cache_config: EmbeddingCacheConfig,
+    ) -> Self {
+        self.embeddings = Some(Arc::new(CachedEmbeddingProvider::new(
+            provider,
+            cache_config,
+        )));
+        self
+    }
+
+    /// Set the embedding provider **without** caching (for tests).
+    pub fn with_embeddings_uncached(mut self, provider: Arc<dyn EmbeddingProvider>) -> Self {
         self.embeddings = Some(provider);
         self
     }

tests/e2e/mock_llm.py

@@ -267,14 +267,24 @@ async def _stream_tool_call(request: web.Request, cid: str, tc: dict) -> web.Str
 async def oauth_exchange(request: web.Request) -> web.Response:
     """Mock OAuth token exchange proxy for E2E tests.
 
-    Accepts form params (code, redirect_uri, code_verifier) and returns
-    a fake token response. Called by ironclaw's exchange_via_proxy() when
-    IRONCLAW_OAUTH_EXCHANGE_URL is set.
+    Accepts the generic hosted OAuth proxy contract used by IronClaw and
+    returns a fake token response. MCP callback tests assert that provider-
+    specific token params such as RFC 8707 `resource` are forwarded here.
     """
     data = await request.post()
     code = data.get("code", "")
+    access_token_field = data.get("access_token_field", "access_token")
+
+    if code == "mock_mcp_code":
+        if not data.get("token_url", "").endswith("/oauth/token"):
+            return web.json_response({"error": "missing_token_url"}, status=400)
+        if not data.get("client_id"):
+            return web.json_response({"error": "missing_client_id"}, status=400)
+        if not data.get("resource"):
+            return web.json_response({"error": "missing_resource"}, status=400)
+
     return web.json_response({
-        "access_token": f"mock-token-{code}",
+        access_token_field: f"mock-token-{code}",
         "refresh_token": "mock-refresh-token",
         "expires_in": 3600,
     })

tests/e2e/scenarios/test_mcp_auth_flow.py

@@ -99,6 +99,10 @@ async def test_mcp_activate_triggers_auth(ironclaw_server):
     assert auth_url is not None or awaiting_token, (
         f"Activate should require auth, got: {data}"
     )
+    if auth_url is not None:
+        assert _extract_state(auth_url).startswith("ic2."), (
+            f"Hosted MCP OAuth should emit versioned state, got: {auth_url}"
+        )
 
 
 # ── Section C: OAuth Round-Trip ──────────────────────────────────────────

tests/relay_integration.rs

@@ -2,18 +2,12 @@
 //!
 //! Uses real HTTP servers on random ports (no mock framework).
 
-use std::convert::Infallible;
-use std::sync::atomic::{AtomicUsize, Ordering};
-
 use axum::{
     Json, Router,
     extract::Query,
-    http::StatusCode,
-    response::sse::{Event, KeepAlive, Sse},
     routing::{get, post},
 };
-use futures::stream;
-use ironclaw::channels::relay::client::{RelayClient, RelayError};
+use ironclaw::channels::relay::client::{ChannelEvent, RelayClient};
 use secrecy::SecretString;
 use serde::Deserialize;
 use tokio::net::TcpListener;
@@ -37,109 +31,79 @@ fn test_client(base_url: &str) -> RelayClient {
     .expect("client build")
 }
 
-// ── SSE stream mock ─────────────────────────────────────────────────────
+// ── Signing secret fetch ─────────────────────────────────────────────────
 
 #[tokio::test]
-async fn test_sse_stream_receives_events() {
+async fn test_get_signing_secret_returns_decoded_bytes() {
+    let secret_hex = hex::encode([1u8; 32]);
+    let secret_hex_clone = secret_hex.clone();
     let app = Router::new().route(
-        "/stream",
-        get(
-            |Query(params): Query<std::collections::HashMap<String, String>>| async move {
-                // Verify token is passed
-                assert!(params.contains_key("token"));
-
-                let events = vec![
-                    Ok::<_, Infallible>(
-                        Event::default().event("message").data(
-                            serde_json::json!({
-                                "event_type": "message",
-                                "provider": "slack",
-                                "provider_scope": "T123",
-                                "channel_id": "C456",
-                                "sender_id": "U789",
-                                "content": "hello world"
-                            })
-                            .to_string(),
-                        ),
-                    ),
-                    Ok(Event::default().event("message").data(
-                        serde_json::json!({
-                            "event_type": "direct_message",
-                            "provider": "slack",
-                            "provider_scope": "T123",
-                            "channel_id": "D001",
-                            "sender_id": "U789",
-                            "content": "dm text"
-                        })
-                        .to_string(),
-                    )),
-                ];
-
-                Sse::new(stream::iter(events)).keep_alive(KeepAlive::default())
-            },
-        ),
-    );
-
-    let base_url = start_server(app).await;
-    let client = test_client(&base_url);
-
-    let (mut event_stream, handle) = client.connect_stream("test-token", 30).await.unwrap();
-
-    use futures::StreamExt;
-    let first = event_stream.next().await.expect("first event");
-    assert_eq!(first.event_type, "message");
-    assert_eq!(first.text(), "hello world");
-    assert_eq!(first.team_id(), "T123");
-
-    let second = event_stream.next().await.expect("second event");
-    assert_eq!(second.event_type, "direct_message");
-    assert_eq!(second.text(), "dm text");
-
-    handle.abort();
-}
-
-// ── Token renewal flow ──────────────────────────────────────────────────
-
-#[tokio::test]
-async fn test_token_expired_returns_error() {
-    let app = Router::new().route("/stream", get(|| async { StatusCode::UNAUTHORIZED }));
-
-    let base_url = start_server(app).await;
-    let client = test_client(&base_url);
-
-    match client.connect_stream("expired-token", 30).await {
-        Err(RelayError::TokenExpired) => {} // expected
-        Err(other) => panic!("expected TokenExpired, got: {other}"),
-        Ok(_) => panic!("expected error, got Ok"),
-    }
-}
-
-#[tokio::test]
-async fn test_token_renewal() {
-    let call_count = std::sync::Arc::new(AtomicUsize::new(0));
-    let call_count_clone = call_count.clone();
-
-    let app = Router::new().route(
-        "/stream/renew",
-        post(move |Json(body): Json<serde_json::Value>| {
-            let count = call_count_clone.clone();
-            async move {
-                count.fetch_add(1, Ordering::SeqCst);
-                assert!(body.get("instance_id").is_some());
-                assert!(body.get("user_id").is_some());
-                Json(serde_json::json!({
-                    "stream_token": "renewed-token-123"
-                }))
-            }
+        "/relay/signing-secret",
+        get(move || {
+            let s = secret_hex_clone.clone();
+            async move { Json(serde_json::json!({"signing_secret": s})) }
         }),
     );
 
     let base_url = start_server(app).await;
     let client = test_client(&base_url);
 
-    let new_token = client.renew_token("inst-1", "user-1").await.unwrap();
-    assert_eq!(new_token, "renewed-token-123");
-    assert_eq!(call_count.load(Ordering::SeqCst), 1);
+    let secret = client.get_signing_secret("T123").await.unwrap();
+    assert_eq!(secret, vec![1u8; 32]);
+}
+
+#[tokio::test]
+async fn test_get_signing_secret_404_returns_error() {
+    let app = Router::new().route(
+        "/relay/signing-secret",
+        get(|| async { (axum::http::StatusCode::NOT_FOUND, "not found") }),
+    );
+
+    let base_url = start_server(app).await;
+    let client = test_client(&base_url);
+
+    let result = client.get_signing_secret("T123").await;
+    assert!(result.is_err());
+}
+
+#[tokio::test]
+async fn test_get_signing_secret_invalid_hex_returns_protocol_error() {
+    let app = Router::new().route(
+        "/relay/signing-secret",
+        get(|| async { Json(serde_json::json!({"signing_secret": "not-hex"})) }),
+    );
+
+    let base_url = start_server(app).await;
+    let client = test_client(&base_url);
+
+    let err = client
+        .get_signing_secret("T123")
+        .await
+        .unwrap_err()
+        .to_string();
+    assert!(err.contains("invalid signing_secret hex"), "got: {err}");
+}
+
+#[tokio::test]
+async fn test_get_signing_secret_wrong_length_returns_protocol_error() {
+    let short_secret_hex = hex::encode([7u8; 31]);
+    let app = Router::new().route(
+        "/relay/signing-secret",
+        get(move || {
+            let s = short_secret_hex.clone();
+            async move { Json(serde_json::json!({"signing_secret": s})) }
+        }),
+    );
+
+    let base_url = start_server(app).await;
+    let client = test_client(&base_url);
+
+    let err = client
+        .get_signing_secret("T123")
+        .await
+        .unwrap_err()
+        .to_string();
+    assert!(err.contains("expected 32 bytes"), "got: {err}");
 }
 
 // ── Proxy call ──────────────────────────────────────────────────────────
@@ -171,7 +135,7 @@ async fn test_proxy_provider_sends_correct_payload() {
         "text": "Hello from test",
     });
     let resp = client
-        .proxy_provider("slack", "T123", "chat.postMessage", body, None)
+        .proxy_provider("slack", "T123", "chat.postMessage", body)
         .await
         .unwrap();
     assert_eq!(resp["ok"], true);
@@ -200,18 +164,18 @@ async fn test_list_connections() {
     assert!(!conns[1].connected);
 }
 
-// ── API key header ──────────────────────────────────────────────────────
+// ── Bearer token auth ────────────────────────────────────────────────────
 
 #[tokio::test]
-async fn test_api_key_sent_in_header() {
+async fn test_bearer_token_sent_in_header() {
     let app = Router::new().route(
         "/connections",
         get(|headers: axum::http::HeaderMap| async move {
-            let key = headers
-                .get("X-API-Key")
+            let auth = headers
+                .get("authorization")
                 .and_then(|v| v.to_str().ok())
                 .unwrap_or("");
-            assert_eq!(key, "test-api-key");
+            assert_eq!(auth, "Bearer test-api-key");
             Json(serde_json::json!([]))
         }),
     );
@@ -233,82 +197,10 @@ fn test_relay_client_new_succeeds() {
     assert!(client.is_ok());
 }
 
-// ── SSE UTF-8 chunk boundary ────────────────────────────────────────────
-
-/// Verify that multi-byte UTF-8 characters split across SSE chunks are
-/// not corrupted (no U+FFFD replacement characters).
-#[tokio::test]
-async fn test_sse_stream_preserves_multibyte_utf8_across_chunks() {
-    use std::sync::atomic::{AtomicBool, Ordering};
-
-    let sent = std::sync::Arc::new(AtomicBool::new(false));
-    let sent_clone = sent.clone();
-
-    let app = Router::new().route(
-        "/stream",
-        get(move |_: Query<std::collections::HashMap<String, String>>| {
-            let sent = sent_clone.clone();
-            async move {
-                // Build SSE payload with emoji that will be split mid-character
-                let event_data = serde_json::json!({
-                    "event_type": "message",
-                    "provider": "slack",
-                    "provider_scope": "T1",
-                    "channel_id": "C1",
-                    "sender_id": "U1",
-                    "content": "hello 🦀 world"
-                });
-                let payload = format!("event: message\ndata: {}\n\n", event_data);
-                let bytes = payload.into_bytes();
-
-                // Split in the middle of the 4-byte crab emoji
-                let crab_pos = bytes
-                    .windows(4)
-                    .position(|w| w == [0xF0, 0x9F, 0xA6, 0x80])
-                    .unwrap();
-                let split_at = crab_pos + 2;
-
-                let chunk1 = bytes[..split_at].to_vec();
-                let chunk2 = bytes[split_at..].to_vec();
-
-                sent.store(true, Ordering::SeqCst);
-
-                let events = vec![
-                    Ok::<_, Infallible>(axum::body::Bytes::from(chunk1)),
-                    Ok(axum::body::Bytes::from(chunk2)),
-                ];
-
-                axum::response::Response::builder()
-                    .header("content-type", "text/event-stream")
-                    .body(axum::body::Body::from_stream(stream::iter(events)))
-                    .unwrap()
-            }
-        }),
-    );
-
-    let base_url = start_server(app).await;
-    let client = test_client(&base_url);
-
-    let (mut event_stream, handle) = client.connect_stream("tok", 30).await.unwrap();
-
-    use futures::StreamExt;
-    let event = event_stream.next().await.expect("should get event");
-    assert_eq!(
-        event.text(),
-        "hello 🦀 world",
-        "emoji should not be corrupted"
-    );
-    assert!(sent.load(Ordering::SeqCst));
-
-    handle.abort();
-}
-
 // ── Channel event field validation ──────────────────────────────────────
 
 #[test]
 fn test_channel_event_missing_fields_detected() {
-    use ironclaw::channels::relay::client::ChannelEvent;
-
     // Event with empty sender_id should be detectable
     let json = r#"{"event_type": "message", "provider_scope": "T1", "channel_id": "C1", "sender_id": "", "content": "test"}"#;
     let event: ChannelEvent = serde_json::from_str(json).unwrap();

tests/workspace_integration.rs

@@ -308,7 +308,7 @@ async fn test_workspace_hybrid_search_with_mock_embeddings() {
 
     // Create workspace with mock embeddings (1536 dimensions to match OpenAI)
     let embeddings = Arc::new(MockEmbeddings::new(1536));
-    let workspace = Workspace::new(user_id, pool.clone()).with_embeddings(embeddings);
+    let workspace = Workspace::new(user_id, pool.clone()).with_embeddings_uncached(embeddings);
 
     // Write documents
     workspace