fix: address PR review comments (round 2)

Human reviewer (zmanian):
- H1: Accept configurable embedding dimension in LanceDbVectorStore::new()
  instead of hardcoding 1536. Dimension is sourced from
  EmbeddingProvider::dimension() at init time.
- H2: Skip double-write of embeddings to DB when external vector store
  is active (pass None to insert_chunk for embedding column).
- H3: Update PR title from "refactor" to "feat" (net-new feature).
- H4: Document non-atomic update_embedding in struct doc comment.

Bot reviewer (Copilot):
- Cache LanceDB table handle via tokio::sync::OnceCell (avoid
  open_table per operation).
- Cache Arc<Schema> in struct (avoid rebuilding per insert).
- Fix error variants: ChunkingFailed → EmbeddingFailed for LanceDB
  store/delete operations.
- Propagate store_embedding errors in reindex_document instead of
  warn-only (prevents silent data loss).
- Prefetch document metadata map in backfill_embeddings to avoid N+1
  queries.
- Add lancedb feature + protoc to CI test matrix so LanceDB tests
  actually run on Linux.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

.env.example

@@ -2,9 +2,16 @@
 DATABASE_URL=postgres://localhost/ironclaw
 DATABASE_POOL_SIZE=10
 
+# Vector store for workspace memory (optional)
+# When set to "lancedb", uses LanceDB for semantic search instead of pgvector/libsql
+# VECTOR_BACKEND=builtin   # default: use database's built-in index (pgvector or libsql_vector_idx); "pgvector" is also accepted as an alias for "builtin"
+# VECTOR_BACKEND=lancedb
+# LANCEDB_PATH=~/.ironclaw/lancedb   # path for LanceDB when VECTOR_BACKEND=lancedb
+
 # LLM Provider
 # LLM_BACKEND=nearai           # default
 # Possible values: nearai, ollama, openai_compatible, openai, anthropic, tinfoil
+# LLM_REQUEST_TIMEOUT_SECS=120  # Increase for local LLMs (Ollama, vLLM, LM Studio)
 
 # === Anthropic Direct ===
 # Two auth modes:

.github/workflows/code_style.yml

@@ -36,6 +36,11 @@ jobs:
       uses: dtolnay/rust-toolchain@stable
       with:
         components: clippy
+    - name: Install protoc (for lancedb)
+      if: matrix.name == 'all-features'
+      uses: arduino/setup-protoc@v3
+      with:
+        repo-token: ${{ secrets.GITHUB_TOKEN }}
     - uses: Swatinem/rust-cache@v2
       with:
         key: clippy-${{ matrix.name }}
@@ -62,6 +67,11 @@ jobs:
       uses: dtolnay/rust-toolchain@stable
       with:
         components: clippy
+    - name: Install protoc (for lancedb)
+      if: matrix.name == 'all-features'
+      uses: arduino/setup-protoc@v3
+      with:
+        repo-token: ${{ secrets.GITHUB_TOKEN }}
     - uses: Swatinem/rust-cache@v2
       with:
         key: clippy-windows-${{ matrix.name }}

.github/workflows/test.yml

@@ -14,7 +14,7 @@ jobs:
       matrix:
         include:
           - name: all-features
-            flags: "--features postgres,libsql,html-to-markdown"
+            flags: "--features postgres,libsql,lancedb,html-to-markdown"
           - name: default
             flags: ""
           - name: libsql-only
@@ -26,6 +26,11 @@ jobs:
         uses: dtolnay/rust-toolchain@stable
         with:
           targets: wasm32-wasip2
+      - name: Install protoc (for lancedb)
+        if: matrix.name == 'all-features'
+        uses: arduino/setup-protoc@v3
+        with:
+          repo-token: ${{ secrets.GITHUB_TOKEN }}
       - uses: Swatinem/rust-cache@v2
         with:
           key: ${{ matrix.name }}
@@ -66,6 +71,11 @@ jobs:
         uses: actions/checkout@v6
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
+      - name: Install protoc (for lancedb)
+        if: matrix.name == 'all-features'
+        uses: arduino/setup-protoc@v3
+        with:
+          repo-token: ${{ secrets.GITHUB_TOKEN }}
       - uses: Swatinem/rust-cache@v2
         with:
           key: windows-${{ matrix.name }}
@@ -82,6 +92,10 @@ jobs:
         uses: dtolnay/rust-toolchain@stable
         with:
           targets: wasm32-wasip2
+      - name: Install protoc (for lancedb)
+        uses: arduino/setup-protoc@v3
+        with:
+          repo-token: ${{ secrets.GITHUB_TOKEN }}
       - uses: Swatinem/rust-cache@v2
         with:
           key: wasm-extensions

.gitignore

@@ -4,8 +4,9 @@
 .env.*
 !.env.example
 
-# Claude Code worktrees
+# Claude Code worktrees and lock files
 .claude/worktrees/
+.claude/scheduled_tasks.lock
 
 # Sidecar tool data
 .sidecar/

Cargo.toml

@@ -73,6 +73,8 @@ toml = "0.8"
 # Core types
 uuid = { version = "1", features = ["v4", "v5", "serde"] }
 chrono = { version = "0.4", features = ["serde"] }
+chrono-tz = "0.10"
+iana-time-zone = "0.1"
 rust_decimal = { version = "1", features = ["serde", "serde-with-str", "maths"] }
 rust_decimal_macros = "1"
 
@@ -123,6 +125,11 @@ open = "5"
 # The postgres feature provides ToSql/FromSql for postgres-types (shared by tokio-postgres)
 pgvector = { version = "0.4", features = ["postgres"], optional = true }
 
+# LanceDB vector store (optional alternative to pgvector/libsql for workspace search)
+lancedb = { version = "0.26", optional = true }
+arrow-array = { version = "57", optional = true }
+arrow-schema = { version = "57", optional = true }
+
 # WASM sandbox for untrusted tool execution
 wasmtime = { version = "28", features = ["component-model"] }
 wasmtime-wasi = "28"  # WASI support for component model
@@ -187,6 +194,7 @@ insta = "1.46.3"
 
 [features]
 default = ["postgres", "libsql", "html-to-markdown"]
+lancedb = ["dep:lancedb", "dep:arrow-array", "dep:arrow-schema"]
 postgres = [
     "dep:deadpool-postgres",
     "dep:tokio-postgres",

FEATURE_PARITY.md

@@ -39,7 +39,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Network modes (loopback/LAN/remote) | ✅ | 🚧 | HTTP only |
 | OpenAI-compatible HTTP API | ✅ | ✅ | /v1/chat/completions, per-request `model` override |
 | Canvas hosting | ✅ | ❌ | Agent-driven UI |
-| Gateway lock (PID-based) | ✅ | ❌ | |
+| Gateway lock (PID-based) | ✅ | ✅ | `fs4` flock-based, acquired in `main.rs` before agent startup |
 | launchd/systemd integration | ✅ | ❌ | |
 | Bonjour/mDNS discovery | ✅ | ❌ | |
 | Tailscale integration | ✅ | ❌ | |
@@ -340,7 +340,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Gemini embeddings | ✅ | ❌ | |
 | Local embeddings | ✅ | ❌ | |
 | SQLite-vec backend | ✅ | ❌ | IronClaw uses PostgreSQL |
-| LanceDB backend | ✅ | ❌ | Configurable auto-capture max length |
+| LanceDB backend | ✅ | ✅ | VectorStore trait + LanceDbVectorStore (configured via VECTOR_BACKEND=lancedb) |
 | QMD backend | ✅ | ❌ | |
 | Atomic reindexing | ✅ | ✅ | |
 | Embeddings batching | ✅ | ✅ | `embed_batch` on EmbeddingProvider trait |

docker-compose.yml

@@ -3,7 +3,7 @@ services:
   postgres:
     image: pgvector/pgvector:pg16
     ports:
-      - "5432:5432"
+      - "127.0.0.1:5432:5432"
     environment:
       POSTGRES_DB: ironclaw
       POSTGRES_USER: ironclaw

src/agent/agent_loop.rs

@@ -356,6 +356,12 @@ impl Agent {
                 if let Some(workspace) = self.workspace() {
                     let mut config = AgentHeartbeatConfig::default()
                         .with_interval(std::time::Duration::from_secs(hb_config.interval_secs));
+                    config.quiet_hours_start = hb_config.quiet_hours_start;
+                    config.quiet_hours_end = hb_config.quiet_hours_end;
+                    config.timezone = hb_config
+                        .timezone
+                        .clone()
+                        .or_else(|| Some(self.config.default_timezone.clone()));
                     if let (Some(user), Some(channel)) =
                         (&hb_config.notify_user, &hb_config.notify_channel)
                     {
@@ -411,7 +417,6 @@ impl Agent {
                         hygiene,
                         workspace.clone(),
                         self.cheap_llm().clone(),
-                        self.safety().clone(),
                         Some(notify_tx),
                         self.store().map(Arc::clone),
                     ))

src/agent/commands.rs

@@ -345,7 +345,6 @@ impl Agent {
             crate::workspace::hygiene::HygieneConfig::default(),
             workspace.clone(),
             self.llm().clone(),
-            self.safety().clone(),
         );
 
         match runner.check_heartbeat().await {
@@ -406,7 +405,7 @@ impl Agent {
             .with_max_tokens(512)
             .with_temperature(0.3);
 
-        let reasoning = Reasoning::new(self.llm().clone(), self.safety().clone());
+        let reasoning = Reasoning::new(self.llm().clone());
         match reasoning.complete(request).await {
             Ok((text, _usage)) => Ok(SubmissionResult::response(format!(
                 "Thread Summary:\n\n{}",
@@ -454,7 +453,7 @@ impl Agent {
             .with_max_tokens(512)
             .with_temperature(0.5);
 
-        let reasoning = Reasoning::new(self.llm().clone(), self.safety().clone());
+        let reasoning = Reasoning::new(self.llm().clone());
         match reasoning.complete(request).await {
             Ok((text, _usage)) => Ok(SubmissionResult::response(format!(
                 "Suggested Next Steps:\n\n{}",
@@ -663,10 +662,14 @@ impl Agent {
                     }
 
                     match self.llm().set_model(requested) {
-                        Ok(()) => Ok(SubmissionResult::response(format!(
-                            "Switched model to: {}",
-                            requested
-                        ))),
+                        Ok(()) => {
+                            // Persist the model choice so it survives restarts.
+                            self.persist_selected_model(requested).await;
+                            Ok(SubmissionResult::response(format!(
+                                "Switched model to: {}",
+                                requested
+                            )))
+                        }
                         Err(e) => Ok(SubmissionResult::error(format!(
                             "Failed to switch model: {}",
                             e
@@ -822,4 +825,42 @@ impl Agent {
             _ => Ok(None),
         }
     }
+
+    /// Persist the selected model to the settings store (DB and/or TOML config).
+    ///
+    /// Best-effort: logs warnings on failure but does not propagate errors,
+    /// since the in-memory model switch already succeeded.
+    async fn persist_selected_model(&self, model: &str) {
+        // 1. Persist to DB if available.
+        if let Some(store) = self.store() {
+            let value = serde_json::Value::String(model.to_string());
+            if let Err(e) = store.set_setting("default", "selected_model", &value).await {
+                tracing::warn!("Failed to persist model to DB: {}", e);
+            }
+        }
+
+        // 2. Update TOML config file if it exists (sync I/O in spawn_blocking).
+        let model_owned = model.to_string();
+        if let Err(e) = tokio::task::spawn_blocking(move || {
+            let toml_path = crate::settings::Settings::default_toml_path();
+            match crate::settings::Settings::load_toml(&toml_path) {
+                Ok(Some(mut settings)) => {
+                    settings.selected_model = Some(model_owned);
+                    if let Err(e) = settings.save_toml(&toml_path) {
+                        tracing::warn!("Failed to persist model to config.toml: {}", e);
+                    }
+                }
+                Ok(None) => {
+                    // No config file on disk; nothing to update.
+                }
+                Err(e) => {
+                    tracing::warn!("Failed to load config.toml for model persistence: {}", e);
+                }
+            }
+        })
+        .await
+        {
+            tracing::warn!("Model TOML persistence task failed: {}", e);
+        }
+    }
 }

src/agent/compaction.rs

@@ -13,7 +13,6 @@ use crate::agent::context_monitor::{CompactionStrategy, ContextBreakdown};
 use crate::agent::session::Thread;
 use crate::error::Error;
 use crate::llm::{ChatMessage, CompletionRequest, LlmProvider, Reasoning};
-use crate::safety::SafetyLayer;
 use crate::workspace::Workspace;
 
 /// Result of a compaction operation.
@@ -34,13 +33,12 @@ pub struct CompactionResult {
 /// Compacts conversation context to stay within limits.
 pub struct ContextCompactor {
     llm: Arc<dyn LlmProvider>,
-    safety: Arc<SafetyLayer>,
 }
 
 impl ContextCompactor {
     /// Create a new context compactor.
-    pub fn new(llm: Arc<dyn LlmProvider>, safety: Arc<SafetyLayer>) -> Self {
-        Self { llm, safety }
+    pub fn new(llm: Arc<dyn LlmProvider>) -> Self {
+        Self { llm }
     }
 
     /// Compact a thread's context using the given strategy.
@@ -233,7 +231,7 @@ Be brief but capture all important details. Use bullet points."#,
             .with_max_tokens(1024)
             .with_temperature(0.3);
 
-        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let reasoning = Reasoning::new(self.llm.clone());
         let (text, _) = reasoning.complete(request).await?;
         Ok(text)
     }
@@ -346,17 +344,11 @@ mod tests {
     // === QA Plan - Compaction strategy tests ===
 
     use crate::agent::context_monitor::CompactionStrategy;
-    use crate::config::SafetyConfig;
-    use crate::safety::SafetyLayer;
     use crate::testing::StubLlm;
 
     /// Helper: build a `ContextCompactor` with the given `StubLlm`.
     fn make_compactor(llm: Arc<StubLlm>) -> ContextCompactor {
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
-        ContextCompactor::new(llm, safety)
+        ContextCompactor::new(llm)
     }
 
     /// Helper: build a thread with `n` completed turns.

src/agent/dispatcher.rs

@@ -50,8 +50,18 @@ impl Agent {
 
         // Load workspace system prompt (identity files: AGENTS.md, SOUL.md, etc.)
         // In group chats, MEMORY.md is excluded to prevent leaking personal context.
+        // Resolve the user's timezone
+        let user_tz = crate::timezone::resolve_timezone(
+            message.timezone.as_deref(),
+            None, // user setting lookup can be added later
+            &self.config.default_timezone,
+        );
+
         let system_prompt = if let Some(ws) = self.workspace() {
-            match ws.system_prompt_for_context(is_group_chat).await {
+            match ws
+                .system_prompt_for_context_tz(is_group_chat, user_tz)
+                .await
+            {
                 Ok(prompt) if !prompt.is_empty() => Some(prompt),
                 Ok(_) => None,
                 Err(e) => {
@@ -103,7 +113,7 @@ impl Agent {
             None
         };
 
-        let mut reasoning = Reasoning::new(self.llm().clone(), self.safety().clone())
+        let mut reasoning = Reasoning::new(self.llm().clone())
             .with_channel(message.channel.clone())
             .with_model_name(self.llm().active_model_name())
             .with_group_chat(is_group_chat);
@@ -130,6 +140,7 @@ impl Agent {
         let mut job_ctx =
             JobContext::with_user(&message.user_id, "chat", "Interactive chat session");
         job_ctx.http_interceptor = self.deps.http_interceptor.clone();
+        job_ctx.user_timezone = user_tz.name().to_string();
 
         // Build system prompts once for this turn. Two variants: with tools
         // (normal iterations) and without (force_text final iteration).
@@ -785,6 +796,7 @@ impl Agent {
                             tool_call_id: tc.id.clone(),
                             context_messages: context_messages.clone(),
                             deferred_tool_calls: tool_calls[approval_idx + 1..].to_vec(),
+                            user_timezone: Some(user_tz.name().to_string()),
                         };
 
                         return Ok(AgenticLoopResult::NeedApproval { pending });
@@ -1146,6 +1158,7 @@ mod tests {
                 max_actions_per_hour: None,
                 max_tool_iterations: 50,
                 auto_approve_tools: false,
+                default_timezone: "UTC".to_string(),
             },
             deps,
             Arc::new(ChannelManager::new()),
@@ -1248,6 +1261,7 @@ mod tests {
                     arguments: serde_json::json!({"message": "done"}),
                 },
             ],
+            user_timezone: None,
         };
 
         let json = serde_json::to_string(&pending).expect("serialize");
@@ -1595,12 +1609,8 @@ mod tests {
         use crate::testing::StubLlm;
 
         let stub = Arc::new(StubLlm::failing_non_transient("ctx-bomb"));
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
 
-        let reasoning = Reasoning::new(stub.clone(), safety);
+        let reasoning = Reasoning::new(stub.clone());
 
         // Build a fat context with lots of history.
         let messages = vec![
@@ -1710,11 +1720,7 @@ mod tests {
         use crate::llm::{Reasoning, ReasoningContext, RespondResult, ToolDefinition};
 
         let provider = Arc::new(AlwaysToolCallProvider);
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
-        let reasoning = Reasoning::new(provider, safety);
+        let reasoning = Reasoning::new(provider);
 
         let tool_def = ToolDefinition {
             name: "echo".to_string(),
@@ -1900,6 +1906,7 @@ mod tests {
                 max_actions_per_hour: None,
                 max_tool_iterations,
                 auto_approve_tools: true,
+                default_timezone: "UTC".to_string(),
             },
             deps,
             Arc::new(ChannelManager::new()),
@@ -2015,6 +2022,7 @@ mod tests {
                     max_actions_per_hour: None,
                     max_tool_iterations: max_iter,
                     auto_approve_tools: true,
+                    default_timezone: "UTC".to_string(),
                 },
                 deps,
                 Arc::new(ChannelManager::new()),

src/agent/heartbeat.rs

@@ -31,7 +31,6 @@ use tokio::sync::mpsc;
 use crate::channels::OutgoingResponse;
 use crate::db::Database;
 use crate::llm::{ChatMessage, CompletionRequest, LlmProvider, Reasoning};
-use crate::safety::SafetyLayer;
 use crate::workspace::Workspace;
 use crate::workspace::hygiene::HygieneConfig;
 
@@ -48,6 +47,12 @@ pub struct HeartbeatConfig {
     pub notify_user_id: Option<String>,
     /// Channel to notify on heartbeat findings.
     pub notify_channel: Option<String>,
+    /// Hour (0-23) when quiet hours start.
+    pub quiet_hours_start: Option<u32>,
+    /// Hour (0-23) when quiet hours end.
+    pub quiet_hours_end: Option<u32>,
+    /// Timezone for quiet hours evaluation (IANA name).
+    pub timezone: Option<String>,
 }
 
 impl Default for HeartbeatConfig {
@@ -58,6 +63,9 @@ impl Default for HeartbeatConfig {
             max_failures: 3,
             notify_user_id: None,
             notify_channel: None,
+            quiet_hours_start: None,
+            quiet_hours_end: None,
+            timezone: None,
         }
     }
 }
@@ -75,6 +83,26 @@ impl HeartbeatConfig {
         self
     }
 
+    /// Check whether the current time falls within configured quiet hours.
+    pub fn is_quiet_hours(&self) -> bool {
+        use chrono::Timelike;
+        let (Some(start), Some(end)) = (self.quiet_hours_start, self.quiet_hours_end) else {
+            return false;
+        };
+        let tz = self
+            .timezone
+            .as_deref()
+            .and_then(crate::timezone::parse_timezone)
+            .unwrap_or(chrono_tz::UTC);
+        let now_hour = crate::timezone::now_in_tz(tz).hour();
+        if start <= end {
+            now_hour >= start && now_hour < end
+        } else {
+            // Wraps midnight, e.g. 22..06
+            now_hour >= start || now_hour < end
+        }
+    }
+
     /// Set the notification target.
     pub fn with_notify(mut self, user_id: impl Into<String>, channel: impl Into<String>) -> Self {
         self.notify_user_id = Some(user_id.into());
@@ -102,7 +130,6 @@ pub struct HeartbeatRunner {
     hygiene_config: HygieneConfig,
     workspace: Arc<Workspace>,
     llm: Arc<dyn LlmProvider>,
-    safety: Arc<SafetyLayer>,
     response_tx: Option<mpsc::Sender<OutgoingResponse>>,
     store: Option<Arc<dyn Database>>,
     consecutive_failures: u32,
@@ -115,14 +142,12 @@ impl HeartbeatRunner {
         hygiene_config: HygieneConfig,
         workspace: Arc<Workspace>,
         llm: Arc<dyn LlmProvider>,
-        safety: Arc<SafetyLayer>,
     ) -> Self {
         Self {
             config,
             hygiene_config,
             workspace,
             llm,
-            safety,
             response_tx: None,
             store: None,
             consecutive_failures: 0,
@@ -162,6 +187,12 @@ impl HeartbeatRunner {
         loop {
             interval.tick().await;
 
+            // Skip during quiet hours
+            if self.config.is_quiet_hours() {
+                tracing::debug!("Heartbeat skipped: quiet hours");
+                continue;
+            }
+
             // Run memory hygiene in the background so it never delays the
             // heartbeat checklist. Failures are logged inside run_if_due.
             let hygiene_workspace = Arc::clone(&self.workspace);
@@ -272,7 +303,7 @@ impl HeartbeatRunner {
             .with_max_tokens(max_tokens)
             .with_temperature(0.3);
 
-        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let reasoning = Reasoning::new(self.llm.clone());
         let (content, _usage) = match reasoning.complete(request).await {
             Ok(r) => r,
             Err(e) => return HeartbeatResult::Failed(format!("LLM call failed: {}", e)),
@@ -386,11 +417,10 @@ pub fn spawn_heartbeat(
     hygiene_config: HygieneConfig,
     workspace: Arc<Workspace>,
     llm: Arc<dyn LlmProvider>,
-    safety: Arc<SafetyLayer>,
     response_tx: Option<mpsc::Sender<OutgoingResponse>>,
     store: Option<Arc<dyn Database>>,
 ) -> tokio::task::JoinHandle<()> {
-    let mut runner = HeartbeatRunner::new(config, hygiene_config, workspace, llm, safety);
+    let mut runner = HeartbeatRunner::new(config, hygiene_config, workspace, llm);
     if let Some(tx) = response_tx {
         runner = runner.with_response_channel(tx);
     }
@@ -532,6 +562,83 @@ mod tests {
         assert!(!is_effectively_empty(content));
     }
 
+    // ==================== quiet hours ====================
+
+    #[test]
+    fn test_quiet_hours_inside() {
+        use chrono::{Timelike, Utc};
+
+        let now_utc = Utc::now();
+        let hour = now_utc.hour();
+        let start = hour;
+        let end = (hour + 1) % 24;
+
+        let config = HeartbeatConfig {
+            quiet_hours_start: Some(start),
+            quiet_hours_end: Some(end),
+            timezone: Some("UTC".to_string()),
+            ..HeartbeatConfig::default()
+        };
+        // Current UTC hour is inside [start, end) by construction
+        assert!(config.is_quiet_hours());
+    }
+
+    #[test]
+    fn test_quiet_hours_outside() {
+        use chrono::{Timelike, Utc};
+
+        let now_utc = Utc::now();
+        let hour = now_utc.hour();
+        let start = (hour + 1) % 24;
+        let end = (hour + 2) % 24;
+
+        let config = HeartbeatConfig {
+            quiet_hours_start: Some(start),
+            quiet_hours_end: Some(end),
+            timezone: Some("UTC".to_string()),
+            ..HeartbeatConfig::default()
+        };
+        // Current UTC hour is outside [start, end) by construction
+        assert!(!config.is_quiet_hours());
+    }
+
+    #[test]
+    fn test_quiet_hours_wraparound_excludes_now() {
+        use chrono::{Timelike, Utc};
+
+        let now_utc = Utc::now();
+        let hour = now_utc.hour();
+        // Window covers all hours except the current one
+        let start = (hour + 1) % 24;
+        let end = hour;
+
+        let config = HeartbeatConfig {
+            quiet_hours_start: Some(start),
+            quiet_hours_end: Some(end),
+            timezone: Some("UTC".to_string()),
+            ..HeartbeatConfig::default()
+        };
+        assert!(!config.is_quiet_hours());
+    }
+
+    #[test]
+    fn test_quiet_hours_none_configured() {
+        let config = HeartbeatConfig::default();
+        assert!(!config.is_quiet_hours());
+    }
+
+    #[test]
+    fn test_quiet_hours_same_start_end() {
+        let config = HeartbeatConfig {
+            quiet_hours_start: Some(10),
+            quiet_hours_end: Some(10),
+            timezone: Some("UTC".to_string()),
+            ..HeartbeatConfig::default()
+        };
+        // start == end means zero-width window, should be false
+        assert!(!config.is_quiet_hours());
+    }
+
     #[test]
     fn test_spawn_heartbeat_accepts_store_param() {
         // Regression: spawn_heartbeat must accept an optional Database store
@@ -543,7 +650,6 @@ mod tests {
             HygieneConfig,
             Arc<crate::workspace::Workspace>,
             Arc<dyn crate::llm::LlmProvider>,
-            Arc<crate::safety::SafetyLayer>,
             Option<tokio::sync::mpsc::Sender<crate::channels::OutgoingResponse>>,
             Option<Arc<dyn crate::db::Database>>,
         ) -> tokio::task::JoinHandle<()> = spawn_heartbeat;

src/agent/routine.rs

@@ -57,7 +57,11 @@ pub struct Routine {
 #[serde(tag = "type", rename_all = "snake_case")]
 pub enum Trigger {
     /// Fire on a cron schedule (e.g. "0 9 * * MON-FRI" or "every 2h").
-    Cron { schedule: String },
+    Cron {
+        schedule: String,
+        #[serde(default)]
+        timezone: Option<String>,
+    },
     /// Fire when a channel message matches a pattern.
     Event {
         /// Optional channel filter (e.g. "telegram", "slack").
@@ -99,7 +103,21 @@ impl Trigger {
                         field: "schedule".into(),
                     })?
                     .to_string();
-                Ok(Trigger::Cron { schedule })
+                let timezone = config
+                    .get("timezone")
+                    .and_then(|v| v.as_str())
+                    .and_then(|tz| {
+                        if crate::timezone::parse_timezone(tz).is_some() {
+                            Some(tz.to_string())
+                        } else {
+                            tracing::warn!(
+                                "Ignoring invalid timezone '{}' from DB for cron trigger",
+                                tz
+                            );
+                            None
+                        }
+                    });
+                Ok(Trigger::Cron { schedule, timezone })
             }
             "event" => {
                 let pattern = config
@@ -137,7 +155,10 @@ impl Trigger {
     /// Serialize trigger-specific config to JSON for DB storage.
     pub fn to_config_json(&self) -> serde_json::Value {
         match self {
-            Trigger::Cron { schedule } => serde_json::json!({ "schedule": schedule }),
+            Trigger::Cron { schedule, timezone } => serde_json::json!({
+                "schedule": schedule,
+                "timezone": timezone,
+            }),
             Trigger::Event { channel, pattern } => serde_json::json!({
                 "pattern": pattern,
                 "channel": channel,
@@ -415,12 +436,25 @@ pub fn content_hash(content: &str) -> u64 {
 }
 
 /// Parse a cron expression and compute the next fire time from now.
-pub fn next_cron_fire(schedule: &str) -> Result<Option<DateTime<Utc>>, RoutineError> {
+///
+/// When `timezone` is provided and valid, the schedule is evaluated in that
+/// timezone and the result is converted back to UTC. Otherwise UTC is used.
+pub fn next_cron_fire(
+    schedule: &str,
+    timezone: Option<&str>,
+) -> Result<Option<DateTime<Utc>>, RoutineError> {
     let cron_schedule =
         cron::Schedule::from_str(schedule).map_err(|e| RoutineError::InvalidCron {
             reason: e.to_string(),
         })?;
-    Ok(cron_schedule.upcoming(Utc).next())
+    if let Some(tz) = timezone.and_then(crate::timezone::parse_timezone) {
+        Ok(cron_schedule
+            .upcoming(tz)
+            .next()
+            .map(|dt| dt.with_timezone(&Utc)))
+    } else {
+        Ok(cron_schedule.upcoming(Utc).next())
+    }
 }
 
 #[cfg(test)]
@@ -433,10 +467,11 @@ mod tests {
     fn test_trigger_roundtrip() {
         let trigger = Trigger::Cron {
             schedule: "0 9 * * MON-FRI".to_string(),
+            timezone: None,
         };
         let json = trigger.to_config_json();
         let parsed = Trigger::from_db("cron", json).expect("parse cron");
-        assert!(matches!(parsed, Trigger::Cron { schedule } if schedule == "0 9 * * MON-FRI"));
+        assert!(matches!(parsed, Trigger::Cron { schedule, .. } if schedule == "0 9 * * MON-FRI"));
     }
 
     #[test]
@@ -509,16 +544,58 @@ mod tests {
     #[test]
     fn test_next_cron_fire_valid() {
         // Every minute should always have a next fire
-        let next = next_cron_fire("* * * * * *").expect("valid cron");
+        let next = next_cron_fire("* * * * * *", None).expect("valid cron");
         assert!(next.is_some());
     }
 
     #[test]
     fn test_next_cron_fire_invalid() {
-        let result = next_cron_fire("not a cron");
+        let result = next_cron_fire("not a cron", None);
         assert!(result.is_err());
     }
 
+    #[test]
+    fn test_trigger_cron_timezone_roundtrip() {
+        let trigger = Trigger::Cron {
+            schedule: "0 9 * * MON-FRI".to_string(),
+            timezone: Some("America/New_York".to_string()),
+        };
+        let json = trigger.to_config_json();
+        let parsed = Trigger::from_db("cron", json).expect("parse cron");
+        assert!(matches!(parsed, Trigger::Cron { schedule, timezone }
+                if schedule == "0 9 * * MON-FRI"
+                && timezone.as_deref() == Some("America/New_York")));
+    }
+
+    #[test]
+    fn test_trigger_cron_no_timezone_backward_compat() {
+        let json = serde_json::json!({"schedule": "0 9 * * *"});
+        let parsed = Trigger::from_db("cron", json).expect("parse cron");
+        assert!(matches!(parsed, Trigger::Cron { timezone, .. } if timezone.is_none()));
+    }
+
+    #[test]
+    fn test_trigger_cron_invalid_timezone_coerced_to_none() {
+        let json = serde_json::json!({"schedule": "0 9 * * *", "timezone": "Fake/Zone"});
+        let parsed = Trigger::from_db("cron", json).expect("parse cron");
+        assert!(
+            matches!(parsed, Trigger::Cron { timezone, .. } if timezone.is_none()),
+            "invalid timezone should be coerced to None"
+        );
+    }
+
+    #[test]
+    fn test_next_cron_fire_with_timezone() {
+        let next_utc = next_cron_fire("0 0 9 * * * *", None)
+            .expect("valid cron")
+            .expect("has next");
+        let next_est = next_cron_fire("0 0 9 * * * *", Some("America/New_York"))
+            .expect("valid cron")
+            .expect("has next");
+        // EST is UTC-5 (or EDT UTC-4), so the UTC result should differ
+        assert_ne!(next_utc, next_est, "timezone should shift the fire time");
+    }
+
     #[test]
     fn test_guardrails_default() {
         let g = RoutineGuardrails::default();
@@ -531,7 +608,8 @@ mod tests {
     fn test_trigger_type_tag() {
         assert_eq!(
             Trigger::Cron {
-                schedule: String::new()
+                schedule: String::new(),
+                timezone: None,
             }
             .type_tag(),
             "cron"

src/agent/routine_engine.rs

@@ -170,7 +170,7 @@ impl RoutineEngine {
                 continue;
             }
 
-            let detail = if let Trigger::Cron { ref schedule } = routine.trigger {
+            let detail = if let Trigger::Cron { ref schedule, .. } = routine.trigger {
                 Some(schedule.clone())
             } else {
                 None
@@ -380,8 +380,12 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
 
     // Update routine runtime state
     let now = Utc::now();
-    let next_fire = if let Trigger::Cron { ref schedule } = routine.trigger {
-        next_cron_fire(schedule).unwrap_or(None)
+    let next_fire = if let Trigger::Cron {
+        ref schedule,
+        ref timezone,
+    } = routine.trigger
+    {
+        next_cron_fire(schedule, timezone.as_deref()).unwrap_or(None)
     } else {
         None
     };
@@ -488,18 +492,13 @@ async fn execute_full_job(
             reason: "scheduler not available".to_string(),
         })?;
 
-    // Set the message tool's default channel/target from the routine's notify config
-    // so the LLM can send results without triggering cross-channel approval.
-    // TODO: This mutates shared global state and can race with concurrent jobs.
-    // Move notify config into JobContext metadata and apply per-job instead.
+    let mut metadata = serde_json::json!({ "max_iterations": max_iterations });
+    // Carry the routine's notify config in job metadata so the message tool
+    // can resolve channel/target per-job without global state mutation.
     if let Some(channel) = &routine.notify.channel {
-        scheduler
-            .tools()
-            .set_message_tool_context(Some(channel.clone()), Some(routine.notify.user.clone()))
-            .await;
+        metadata["notify_channel"] = serde_json::json!(channel);
     }
-
-    let metadata = serde_json::json!({ "max_iterations": max_iterations });
+    metadata["notify_user"] = serde_json::json!(&routine.notify.user);
 
     // Build approval context: UnlessAutoApproved tools are auto-approved for routines;
     // Always tools require explicit listing in tool_permissions.

src/agent/session.rs

@@ -164,6 +164,10 @@ pub struct PendingApproval {
     /// executed yet when approval was requested.
     #[serde(default)]
     pub deferred_tool_calls: Vec<ToolCall>,
+    /// User timezone at the time the approval was requested, so it persists
+    /// through the approval flow even if the approval message lacks timezone.
+    #[serde(default)]
+    pub user_timezone: Option<String>,
 }
 
 /// A conversation thread within a session.
@@ -976,6 +980,7 @@ mod tests {
             tool_call_id: "call_123".to_string(),
             context_messages: vec![ChatMessage::user("do it")],
             deferred_tool_calls: vec![],
+            user_timezone: None,
         };
 
         thread.await_approval(approval);
@@ -1001,6 +1006,7 @@ mod tests {
             tool_call_id: "call_456".to_string(),
             context_messages: vec![],
             deferred_tool_calls: vec![],
+            user_timezone: None,
         };
 
         thread.await_approval(approval);

src/agent/thread_ops.rs

@@ -230,7 +230,7 @@ impl Agent {
                     )
                     .await;
 
-                let compactor = ContextCompactor::new(self.llm().clone(), self.safety().clone());
+                let compactor = ContextCompactor::new(self.llm().clone());
                 if let Err(e) = compactor
                     .compact(thread, strategy, self.workspace().map(|w| w.as_ref()))
                     .await
@@ -627,7 +627,7 @@ impl Agent {
                 crate::agent::context_monitor::CompactionStrategy::Summarize { keep_recent: 5 },
             );
 
-        let compactor = ContextCompactor::new(self.llm().clone(), self.safety().clone());
+        let compactor = ContextCompactor::new(self.llm().clone());
         match compactor
             .compact(thread, strategy, self.workspace().map(|w| w.as_ref()))
             .await
@@ -746,6 +746,16 @@ impl Agent {
             let mut job_ctx =
                 JobContext::with_user(&message.user_id, "chat", "Interactive chat session");
             job_ctx.http_interceptor = self.deps.http_interceptor.clone();
+            // Prefer a valid timezone from the approval message, fall back to the
+            // resolved timezone stored when the approval was originally requested.
+            let tz_candidate = message
+                .timezone
+                .as_deref()
+                .filter(|tz| crate::timezone::parse_timezone(tz).is_some())
+                .or(pending.user_timezone.as_deref());
+            if let Some(tz) = tz_candidate {
+                job_ctx.user_timezone = tz.to_string();
+            }
 
             let _ = self
                 .channels
@@ -1111,6 +1121,8 @@ impl Agent {
                     tool_call_id: tc.id.clone(),
                     context_messages: context_messages.clone(),
                     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(),
                 };
 
                 let request_id = new_pending.request_id;

src/agent/worker.rs

@@ -212,7 +212,7 @@ impl Worker {
         let job_ctx = self.context_manager().get_context(self.job_id).await?;
 
         // Create reasoning engine
-        let reasoning = Reasoning::new(self.llm().clone(), self.safety().clone());
+        let reasoning = Reasoning::new(self.llm().clone());
 
         // Build initial reasoning context (tool definitions refreshed each iteration in execution_loop)
         let mut reason_ctx = ReasoningContext::new().with_job(&job_ctx.description);

src/app.rs

@@ -255,15 +255,18 @@ impl AppBuilder {
                     self.libsql_db.take();
                 }
 
-                // Re-resolve config with OS credentials
-                if let Some(ref db) = self.db {
-                    let toml_path = self.toml_path.as_deref();
-                    if let Ok(refreshed) =
-                        Config::from_db_with_toml(db.as_ref(), "default", toml_path).await
-                    {
-                        self.config = refreshed;
-                        tracing::debug!("LlmConfig re-resolved after OS credential injection");
-                    }
+                // Re-resolve only the LLM config with OS credentials.
+                let store: Option<&(dyn crate::db::SettingsStore + Sync)> =
+                    self.db.as_ref().map(|db| db.as_ref() as _);
+                let toml_path = self.toml_path.as_deref();
+                if let Err(e) = self
+                    .config
+                    .re_resolve_llm(store, "default", toml_path)
+                    .await
+                {
+                    tracing::warn!(
+                        "Failed to re-resolve LLM config after OS credential injection: {e}"
+                    );
                 }
 
                 return Ok(());
@@ -308,18 +311,16 @@ impl AppBuilder {
             // Inject LLM API keys from encrypted storage
             crate::config::inject_llm_keys_from_secrets(secrets.as_ref(), "default").await;
 
-            // Re-resolve config with newly available keys
-            if let Some(ref db) = self.db {
-                let toml_path = self.toml_path.as_deref();
-                match Config::from_db_with_toml(db.as_ref(), "default", toml_path).await {
-                    Ok(refreshed) => {
-                        self.config = refreshed;
-                        tracing::debug!("LlmConfig re-resolved after secret injection");
-                    }
-                    Err(e) => {
-                        tracing::warn!("Failed to re-resolve config after secret injection: {}", e);
-                    }
-                }
+            // Re-resolve only the LLM config with newly available keys.
+            let store: Option<&(dyn crate::db::SettingsStore + Sync)> =
+                self.db.as_ref().map(|db| db.as_ref() as _);
+            let toml_path = self.toml_path.as_deref();
+            if let Err(e) = self
+                .config
+                .re_resolve_llm(store, "default", toml_path)
+                .await
+            {
+                tracing::warn!("Failed to re-resolve LLM config after secret injection: {e}");
             }
         }
 
@@ -385,12 +386,53 @@ impl AppBuilder {
             .embeddings
             .create_provider(&self.config.llm.nearai.base_url, self.session.clone());
 
+        // Create optional external vector store for workspace semantic search
+        let vector_store: Option<Arc<dyn crate::workspace::VectorStore>> = {
+            #[cfg(feature = "lancedb")]
+            {
+                if self.config.database.vector_backend == crate::config::VectorBackend::LanceDb {
+                    let path = self
+                        .config
+                        .database
+                        .lancedb_path
+                        .clone()
+                        .unwrap_or_else(crate::config::default_lancedb_path);
+                    let dim = embeddings.as_ref().map(|p| p.dimension());
+                    match crate::workspace::LanceDbVectorStore::new(path, dim).await {
+                        Ok(store) => {
+                            tracing::info!("LanceDB vector store connected for workspace search");
+                            Some(Arc::new(store) as Arc<dyn crate::workspace::VectorStore>)
+                        }
+                        Err(e) => {
+                            tracing::warn!("Failed to initialize LanceDB: {}", e);
+                            None
+                        }
+                    }
+                } else {
+                    None
+                }
+            }
+            #[cfg(not(feature = "lancedb"))]
+            {
+                if self.config.database.vector_backend == crate::config::VectorBackend::LanceDb {
+                    tracing::warn!(
+                        "VECTOR_BACKEND=lancedb but 'lancedb' feature not enabled; \
+                         falling back to built-in vector search"
+                    );
+                }
+                None
+            }
+        };
+
         // Register memory tools if database is available
         let workspace = if let Some(ref db) = self.db {
             let mut ws = Workspace::new_with_db("default", db.clone());
             if let Some(ref emb) = embeddings {
                 ws = ws.with_embeddings(emb.clone());
             }
+            if let Some(ref vs) = vector_store {
+                ws = ws.with_vector_store(vs.clone());
+            }
             let ws = Arc::new(ws);
             tools.register_memory_tools(Arc::clone(&ws));
             Some(ws)
@@ -403,11 +445,7 @@ impl AppBuilder {
             && (self.config.agent.allow_local_tools || !self.config.sandbox.enabled)
         {
             tools
-                .register_builder_tool(
-                    llm.clone(),
-                    safety.clone(),
-                    Some(self.config.builder.to_builder_config()),
-                )
+                .register_builder_tool(llm.clone(), Some(self.config.builder.to_builder_config()))
                 .await;
             tracing::info!("Builder mode enabled");
         }
@@ -542,7 +580,7 @@ impl AppBuilder {
                                             server, mcp_sm, secrets, "default",
                                         )
                                     } else {
-                                        McpClient::new_with_config(server.clone())
+                                        McpClient::new_with_name(&server_name, &server.url)
                                     };
 
                                     match client.list_tools().await {

src/bootstrap.rs

@@ -414,10 +414,103 @@ pub enum MigrationError {
     Io(String),
 }
 
+// ── PID Lock ──────────────────────────────────────────────────────────────
+
+/// Path to the PID lock file: `~/.ironclaw/ironclaw.pid`.
+pub fn pid_lock_path() -> PathBuf {
+    ironclaw_base_dir().join("ironclaw.pid")
+}
+
+/// A PID-based lock that prevents multiple IronClaw instances from running
+/// simultaneously.
+///
+/// Uses `fs4::try_lock_exclusive()` for atomic locking (no TOCTOU race),
+/// then writes the current PID into the locked file for diagnostics.
+/// The OS-level lock is held for the lifetime of this struct and
+/// automatically released on drop (along with the PID file cleanup).
+#[derive(Debug)]
+pub struct PidLock {
+    path: PathBuf,
+    /// Held open to maintain the OS-level exclusive lock.
+    _file: std::fs::File,
+}
+
+/// Errors from PID lock acquisition.
+#[derive(Debug, thiserror::Error)]
+pub enum PidLockError {
+    #[error("Another IronClaw instance is already running (PID {pid})")]
+    AlreadyRunning { pid: u32 },
+    #[error("Failed to acquire PID lock: {0}")]
+    Io(#[from] std::io::Error),
+}
+
+impl PidLock {
+    /// Try to acquire the PID lock.
+    ///
+    /// Uses an exclusive file lock (`flock`/`LockFileEx`) so that two
+    /// concurrent processes cannot both acquire the lock — no TOCTOU race.
+    /// If the lock file exists but the holding process is gone (stale),
+    /// the lock is reclaimed automatically by the OS.
+    pub fn acquire() -> Result<Self, PidLockError> {
+        Self::acquire_at(pid_lock_path())
+    }
+
+    /// Acquire at a specific path (for testing).
+    fn acquire_at(path: PathBuf) -> Result<Self, PidLockError> {
+        use fs4::FileExt;
+        use std::fs::OpenOptions;
+        use std::io::Write;
+
+        // Ensure parent directory exists
+        if let Some(parent) = path.parent() {
+            std::fs::create_dir_all(parent)?;
+        }
+
+        // Open (or create) the lock file
+        let mut file = OpenOptions::new()
+            .read(true)
+            .write(true)
+            .create(true)
+            .truncate(false)
+            .open(&path)?;
+
+        // Try non-blocking exclusive lock — if another process holds it,
+        // this fails immediately instead of blocking.
+        if let Err(e) = file.try_lock_exclusive() {
+            if e.kind() == std::io::ErrorKind::WouldBlock {
+                // Lock held by another process — read its PID for the error message
+                let pid = std::fs::read_to_string(&path)
+                    .ok()
+                    .and_then(|s| s.trim().parse::<u32>().ok())
+                    .unwrap_or(0);
+                return Err(PidLockError::AlreadyRunning { pid });
+            }
+            // Other errors (permissions, unsupported filesystem, etc.)
+            return Err(PidLockError::Io(e));
+        }
+
+        // We hold the exclusive lock — write our PID
+        file.set_len(0)?; // truncate
+        write!(file, "{}", std::process::id())?;
+
+        Ok(PidLock { path, _file: file })
+    }
+}
+
+impl Drop for PidLock {
+    fn drop(&mut self) {
+        // Remove the PID file; the OS-level lock is released when _file is dropped.
+        let _ = std::fs::remove_file(&self.path);
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
+    use std::process::Command;
     use std::sync::Mutex;
+    use std::thread;
+    use std::time::{Duration, Instant};
     use tempfile::tempdir;
 
     static ENV_MUTEX: Mutex<()> = Mutex::new(());
@@ -986,4 +1079,162 @@ INJECTED="pwned"#;
             unsafe { std::env::remove_var("IRONCLAW_BASE_DIR") };
         }
     }
+
+    // ── PID Lock tests ───────────────────────────────────────────────
+
+    #[test]
+    fn test_pid_lock_acquire_and_drop() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        // Acquire lock
+        let lock = PidLock::acquire_at(pid_path.clone()).unwrap();
+        assert!(pid_path.exists());
+
+        // PID file should contain our PID
+        let contents = std::fs::read_to_string(&pid_path).unwrap();
+        assert_eq!(contents.trim().parse::<u32>().unwrap(), std::process::id());
+
+        // Drop should remove the file
+        drop(lock);
+        assert!(!pid_path.exists());
+    }
+
+    #[test]
+    fn test_pid_lock_rejects_second_acquire() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        // First lock succeeds
+        let _lock1 = PidLock::acquire_at(pid_path.clone()).unwrap();
+
+        // Second acquire on same file must fail (exclusive flock held)
+        let result = PidLock::acquire_at(pid_path.clone());
+        assert!(result.is_err());
+        match result.unwrap_err() {
+            PidLockError::AlreadyRunning { pid } => {
+                assert_eq!(pid, std::process::id());
+            }
+            other => panic!("expected AlreadyRunning, got: {}", other),
+        }
+    }
+
+    #[test]
+    fn test_pid_lock_reclaims_after_drop() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        // Acquire and release
+        let lock = PidLock::acquire_at(pid_path.clone()).unwrap();
+        drop(lock);
+
+        // Should succeed — OS lock was released on drop
+        let lock2 = PidLock::acquire_at(pid_path).unwrap();
+        drop(lock2);
+    }
+
+    #[test]
+    fn test_pid_lock_reclaims_stale_file_without_flock() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        // Write a stale PID file manually (no flock held)
+        std::fs::write(&pid_path, "4294967294").unwrap();
+
+        // Should succeed because no OS lock is held on the file
+        let lock = PidLock::acquire_at(pid_path.clone()).unwrap();
+        let contents = std::fs::read_to_string(&pid_path).unwrap();
+        assert_eq!(contents.trim().parse::<u32>().unwrap(), std::process::id());
+        drop(lock);
+    }
+
+    #[test]
+    fn test_pid_lock_handles_corrupt_pid_file() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        // Write garbage (no flock held)
+        std::fs::write(&pid_path, "not-a-number").unwrap();
+
+        // Should succeed — no OS lock held, file is reclaimed
+        let lock = PidLock::acquire_at(pid_path).unwrap();
+        drop(lock);
+    }
+
+    #[test]
+    fn test_pid_lock_creates_parent_dirs() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("nested").join("deep").join("ironclaw.pid");
+
+        let lock = PidLock::acquire_at(pid_path.clone()).unwrap();
+        assert!(pid_path.exists());
+        drop(lock);
+    }
+
+    #[test]
+    fn test_pid_lock_child_helper_holds_lock() {
+        if std::env::var("IRONCLAW_PID_LOCK_CHILD").ok().as_deref() != Some("1") {
+            return;
+        }
+
+        let pid_path = PathBuf::from(
+            std::env::var("IRONCLAW_PID_LOCK_PATH").expect("IRONCLAW_PID_LOCK_PATH missing"),
+        );
+        let hold_ms = std::env::var("IRONCLAW_PID_LOCK_HOLD_MS")
+            .ok()
+            .and_then(|s| s.parse::<u64>().ok())
+            .unwrap_or(3000);
+
+        let _lock = PidLock::acquire_at(pid_path).expect("child failed to acquire pid lock");
+        thread::sleep(Duration::from_millis(hold_ms));
+    }
+
+    #[test]
+    fn test_pid_lock_rejects_lock_held_by_other_process() {
+        let dir = tempdir().unwrap();
+        let pid_path = dir.path().join("ironclaw.pid");
+
+        let current_exe = std::env::current_exe().unwrap();
+        let mut child = Command::new(current_exe)
+            .args([
+                "--exact",
+                "bootstrap::tests::test_pid_lock_child_helper_holds_lock",
+                "--nocapture",
+                "--test-threads=1",
+            ])
+            .env("IRONCLAW_PID_LOCK_CHILD", "1")
+            .env("IRONCLAW_PID_LOCK_PATH", pid_path.display().to_string())
+            .env("IRONCLAW_PID_LOCK_HOLD_MS", "3000")
+            .spawn()
+            .unwrap();
+
+        let started = Instant::now();
+        while started.elapsed() < Duration::from_secs(2) {
+            if pid_path.exists() {
+                break;
+            }
+            if let Some(status) = child.try_wait().unwrap() {
+                panic!("child exited before acquiring lock: {}", status);
+            }
+            thread::sleep(Duration::from_millis(20));
+        }
+        assert!(
+            pid_path.exists(),
+            "child did not create lock file in time: {}",
+            pid_path.display()
+        );
+
+        let result = PidLock::acquire_at(pid_path.clone());
+        match result.unwrap_err() {
+            PidLockError::AlreadyRunning { .. } => {}
+            other => panic!("expected AlreadyRunning, got: {}", other),
+        }
+
+        let status = child.wait().unwrap();
+        assert!(status.success(), "child process failed: {}", status);
+
+        // After the child exits, lock should be released and reacquirable.
+        let lock = PidLock::acquire_at(pid_path).unwrap();
+        drop(lock);
+    }
 }

src/channels/channel.rs

@@ -79,6 +79,8 @@ pub struct IncomingMessage {
     pub received_at: DateTime<Utc>,
     /// Channel-specific metadata.
     pub metadata: serde_json::Value,
+    /// IANA timezone string from the client (e.g. "America/New_York").
+    pub timezone: Option<String>,
     /// File or media attachments on this message.
     pub attachments: Vec<IncomingAttachment>,
 }
@@ -99,6 +101,7 @@ impl IncomingMessage {
             thread_id: None,
             received_at: Utc::now(),
             metadata: serde_json::Value::Null,
+            timezone: None,
             attachments: Vec::new(),
         }
     }
@@ -121,6 +124,12 @@ impl IncomingMessage {
         self
     }
 
+    /// Set the client timezone.
+    pub fn with_timezone(mut self, tz: impl Into<String>) -> Self {
+        self.timezone = Some(tz.into());
+        self
+    }
+
     /// Set attachments.
     pub fn with_attachments(mut self, attachments: Vec<IncomingAttachment>) -> Self {
         self.attachments = attachments;
@@ -454,4 +463,10 @@ mod tests {
             panic!("expected ToolCompleted variant");
         }
     }
+
+    #[test]
+    fn test_incoming_message_with_timezone() {
+        let msg = IncomingMessage::new("test", "user1", "hello").with_timezone("America/New_York");
+        assert_eq!(msg.timezone.as_deref(), Some("America/New_York"));
+    }
 }

src/channels/repl.rs

@@ -18,7 +18,7 @@
 //! - `Esc` - Interrupt current operation
 
 use std::borrow::Cow;
-use std::io::{self, Write};
+use std::io::{self, IsTerminal, Write};
 use std::sync::Arc;
 use std::sync::atomic::{AtomicBool, Ordering};
 
@@ -297,10 +297,15 @@ impl Channel for ReplChannel {
         let esc_interrupt_triggered_for_thread = Arc::new(AtomicBool::new(false));
 
         std::thread::spawn(move || {
+            let sys_tz = crate::timezone::detect_system_timezone().name().to_string();
+
             // Single message mode: send it and return
             if let Some(msg) = single_message {
-                let incoming = IncomingMessage::new("repl", "default", &msg);
+                let incoming = IncomingMessage::new("repl", "default", &msg).with_timezone(&sys_tz);
                 let _ = tx.blocking_send(incoming);
+                // Ensure the agent exits after handling exactly one turn in -m mode,
+                // even when other channels (gateway/http) are enabled.
+                let _ = tx.blocking_send(IncomingMessage::new("repl", "default", "/quit"));
                 return;
             }
 
@@ -361,7 +366,8 @@ impl Channel for ReplChannel {
                             "/quit" | "/exit" => {
                                 // Forward shutdown command so the agent loop exits even
                                 // when other channels (e.g. web gateway) are still active.
-                                let msg = IncomingMessage::new("repl", "default", "/quit");
+                                let msg = IncomingMessage::new("repl", "default", "/quit")
+                                    .with_timezone(&sys_tz);
                                 let _ = tx.blocking_send(msg);
                                 break;
                             }
@@ -382,7 +388,8 @@ impl Channel for ReplChannel {
                             _ => {}
                         }
 
-                        let msg = IncomingMessage::new("repl", "default", line);
+                        let msg =
+                            IncomingMessage::new("repl", "default", line).with_timezone(&sys_tz);
                         if tx.blocking_send(msg).is_err() {
                             break;
                         }
@@ -390,21 +397,29 @@ impl Channel for ReplChannel {
                     Err(ReadlineError::Interrupted) => {
                         if esc_interrupt_triggered_for_thread.swap(false, Ordering::Relaxed) {
                             // Esc: interrupt current operation and keep REPL open.
-                            let msg = IncomingMessage::new("repl", "default", "/interrupt");
+                            let msg = IncomingMessage::new("repl", "default", "/interrupt")
+                                .with_timezone(&sys_tz);
                             if tx.blocking_send(msg).is_err() {
                                 break;
                             }
                         } else {
                             // Ctrl+C (VINTR): request graceful shutdown.
-                            let msg = IncomingMessage::new("repl", "default", "/quit");
+                            let msg = IncomingMessage::new("repl", "default", "/quit")
+                                .with_timezone(&sys_tz);
                             let _ = tx.blocking_send(msg);
                             break;
                         }
                     }
                     Err(ReadlineError::Eof) => {
-                        // Ctrl+D: send /quit so the agent loop runs graceful shutdown
-                        let msg = IncomingMessage::new("repl", "default", "/quit");
-                        let _ = tx.blocking_send(msg);
+                        // Ctrl+D in interactive mode: graceful shutdown.
+                        // In daemon mode (stdin = /dev/null, no TTY), EOF arrives
+                        // immediately — just drop the REPL thread silently so other
+                        // channels (gateway, telegram, …) keep running.
+                        if std::io::stdin().is_terminal() {
+                            let msg = IncomingMessage::new("repl", "default", "/quit")
+                                .with_timezone(&sys_tz);
+                            let _ = tx.blocking_send(msg);
+                        }
                         break;
                     }
                     Err(e) => {
@@ -614,3 +629,29 @@ impl Channel for ReplChannel {
         Ok(())
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use futures::StreamExt;
+
+    use super::*;
+
+    #[tokio::test]
+    async fn single_message_mode_sends_message_then_quit() {
+        let repl = ReplChannel::with_message("hi".to_string());
+        let mut stream = repl.start().await.expect("repl start should succeed");
+
+        let first = stream.next().await.expect("first message missing");
+        assert_eq!(first.channel, "repl");
+        assert_eq!(first.content, "hi");
+
+        let second = stream.next().await.expect("quit message missing");
+        assert_eq!(second.channel, "repl");
+        assert_eq!(second.content, "/quit");
+
+        assert!(
+            stream.next().await.is_none(),
+            "stream should end after /quit"
+        );
+    }
+}

src/channels/web/handlers/routines.rs

@@ -264,7 +264,7 @@ pub async fn routines_runs_handler(
 /// Convert a Routine to the trimmed RoutineInfo for list display.
 fn routine_to_info(r: &crate::agent::routine::Routine) -> RoutineInfo {
     let (trigger_type, trigger_summary) = match &r.trigger {
-        crate::agent::routine::Trigger::Cron { schedule } => {
+        crate::agent::routine::Trigger::Cron { schedule, .. } => {
             ("cron".to_string(), format!("cron: {}", schedule))
         }
         crate::agent::routine::Trigger::Event {

src/channels/web/server.rs

@@ -610,6 +610,7 @@ async fn oauth_callback_handler(
 
 async fn chat_send_handler(
     State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
     Json(req): Json<SendMessageRequest>,
 ) -> Result<(StatusCode, Json<SendMessageResponse>), (StatusCode, String)> {
     tracing::debug!(
@@ -626,6 +627,14 @@ async fn chat_send_handler(
     }
 
     let mut msg = IncomingMessage::new("gateway", &state.user_id, &req.content);
+    // Prefer timezone from JSON body, fall back to X-Timezone header
+    let tz = req
+        .timezone
+        .as_deref()
+        .or_else(|| headers.get("X-Timezone").and_then(|v| v.to_str().ok()));
+    if let Some(tz) = tz {
+        msg = msg.with_timezone(tz);
+    }
 
     if let Some(ref thread_id) = req.thread_id {
         msg = msg.with_thread(thread_id);
@@ -2115,7 +2124,7 @@ async fn routines_runs_handler(
 /// Convert a Routine to the trimmed RoutineInfo for list display.
 fn routine_to_info(r: &crate::agent::routine::Routine) -> RoutineInfo {
     let (trigger_type, trigger_summary) = match &r.trigger {
-        crate::agent::routine::Trigger::Cron { schedule } => {
+        crate::agent::routine::Trigger::Cron { schedule, .. } => {
             ("cron".to_string(), format!("cron: {}", schedule))
         }
         crate::agent::routine::Trigger::Event {

src/channels/web/static/app.js

@@ -181,6 +181,7 @@ function confirmRestart() {
     body: {
       content: '/restart',
       thread_id: currentThreadId,
+      timezone: Intl.DateTimeFormat().resolvedOptions().timeZone,
     },
   })
     .then((response) => {
@@ -454,7 +455,7 @@ function sendMessage() {
 
   apiFetch('/api/chat/send', {
     method: 'POST',
-    body: { content, thread_id: currentThreadId || undefined },
+    body: { content, thread_id: currentThreadId || undefined, timezone: Intl.DateTimeFormat().resolvedOptions().timeZone },
   }).catch((err) => {
     addMessage('system', 'Failed to send: ' + err.message);
   });
@@ -563,6 +564,13 @@ function sendApprovalAction(requestId, action) {
 
 function renderMarkdown(text) {
   if (typeof marked !== 'undefined') {
+    // Escape raw HTML error pages instead of rendering them as markup.
+    // Only triggers when the text *starts with* a doctype or <html> tag
+    // (after optional whitespace), so normal messages that mention HTML
+    // tags in prose or code fences are not affected.  See #263.
+    if (/^\s*<!doctype\s/i.test(text) || /^\s*<html[\s>]/i.test(text)) {
+      return escapeHtml(text);
+    }
     let html = marked.parse(text);
     // Sanitize HTML output to prevent XSS from tool output or LLM responses.
     html = sanitizeRenderedHtml(html);
@@ -1473,7 +1481,7 @@ chatInput.addEventListener('keydown', (e) => {
     }
   }
 
-  if (e.key === 'Enter' && !e.shiftKey) {
+  if (e.key === 'Enter' && !e.shiftKey && !e.isComposing) {
     e.preventDefault();
     hideSlashAutocomplete();
     sendMessage();

src/channels/web/types.rs

@@ -9,6 +9,7 @@ use uuid::Uuid;
 pub struct SendMessageRequest {
     pub content: String,
     pub thread_id: Option<String>,
+    pub timezone: Option<String>,
 }
 
 #[derive(Debug, Serialize)]
@@ -613,6 +614,7 @@ pub enum WsClientMessage {
     Message {
         content: String,
         thread_id: Option<String>,
+        timezone: Option<String>,
     },
     /// Approve or deny a pending tool execution.
     #[serde(rename = "approval")]
@@ -798,7 +800,9 @@ mod tests {
         let json = r#"{"type":"message","content":"hello","thread_id":"t1"}"#;
         let msg: WsClientMessage = serde_json::from_str(json).unwrap();
         match msg {
-            WsClientMessage::Message { content, thread_id } => {
+            WsClientMessage::Message {
+                content, thread_id, ..
+            } => {
                 assert_eq!(content, "hello");
                 assert_eq!(thread_id.as_deref(), Some("t1"));
             }
@@ -811,7 +815,9 @@ mod tests {
         let json = r#"{"type":"message","content":"hi"}"#;
         let msg: WsClientMessage = serde_json::from_str(json).unwrap();
         match msg {
-            WsClientMessage::Message { content, thread_id } => {
+            WsClientMessage::Message {
+                content, thread_id, ..
+            } => {
                 assert_eq!(content, "hi");
                 assert!(thread_id.is_none());
             }

src/channels/web/ws.rs

@@ -156,8 +156,15 @@ async fn handle_client_message(
     direct_tx: &mpsc::Sender<WsServerMessage>,
 ) {
     match msg {
-        WsClientMessage::Message { content, thread_id } => {
+        WsClientMessage::Message {
+            content,
+            thread_id,
+            timezone,
+        } => {
             let mut incoming = IncomingMessage::new("gateway", user_id, &content);
+            if let Some(ref tz) = timezone {
+                incoming = incoming.with_timezone(tz);
+            }
             if let Some(ref tid) = thread_id {
                 incoming = incoming.with_thread(tid);
             }
@@ -349,6 +356,7 @@ mod tests {
             WsClientMessage::Message {
                 content: "hello agent".to_string(),
                 thread_id: Some("t1".to_string()),
+                timezone: None,
             },
             &state,
             "user1",
@@ -373,6 +381,7 @@ mod tests {
             WsClientMessage::Message {
                 content: "hello".to_string(),
                 thread_id: None,
+                timezone: None,
             },
             &state,
             "user1",

src/cli/mcp.rs

@@ -47,10 +47,6 @@ pub enum McpCommand {
         /// Server description
         #[arg(long)]
         description: Option<String>,
-
-        /// Custom HTTP headers (format: "Key:Value", can be repeated)
-        #[arg(long = "header", short = 'H')]
-        headers: Vec<String>,
     },
 
     /// Remove an MCP server
@@ -112,7 +108,6 @@ pub async fn run_mcp_command(cmd: McpCommand) -> anyhow::Result<()> {
             token_url,
             scopes,
             description,
-            headers,
         } => {
             add_server(
                 name,
@@ -122,7 +117,6 @@ pub async fn run_mcp_command(cmd: McpCommand) -> anyhow::Result<()> {
                 token_url,
                 scopes,
                 description,
-                headers,
             )
             .await
         }
@@ -139,7 +133,6 @@ pub async fn run_mcp_command(cmd: McpCommand) -> anyhow::Result<()> {
 }
 
 /// Add a new MCP server.
-#[allow(clippy::too_many_arguments)]
 async fn add_server(
     name: String,
     url: String,
@@ -148,7 +141,6 @@ async fn add_server(
     token_url: Option<String>,
     scopes: Option<String>,
     description: Option<String>,
-    headers: Vec<String>,
 ) -> anyhow::Result<()> {
     let mut config = McpServerConfig::new(&name, &url);
 
@@ -156,18 +148,6 @@ async fn add_server(
         config = config.with_description(desc);
     }
 
-    // Parse custom headers (format: "Key:Value")
-    if !headers.is_empty() {
-        let mut header_map = std::collections::HashMap::new();
-        for h in &headers {
-            let (key, value) = h.split_once(':').ok_or_else(|| {
-                anyhow::anyhow!("Invalid header format '{}'. Expected 'Key:Value'.", h)
-            })?;
-            header_map.insert(key.trim().to_string(), value.trim().to_string());
-        }
-        config = config.with_headers(header_map);
-    }
-
     // Track if auth is required
     let requires_auth = client_id.is_some();
 
@@ -262,17 +242,6 @@ async fn list_servers(verbose: bool) -> anyhow::Result<()> {
             if let Some(ref desc) = server.description {
                 println!("      Description: {}", desc);
             }
-            if !server.headers.is_empty() {
-                println!(
-                    "      Custom headers: {}",
-                    server
-                        .headers
-                        .keys()
-                        .cloned()
-                        .collect::<Vec<_>>()
-                        .join(", ")
-                );
-            }
             if let Some(ref oauth) = server.oauth {
                 println!("      OAuth Client ID: {}", oauth.client_id);
                 if !oauth.scopes.is_empty() {
@@ -405,7 +374,7 @@ async fn test_server(name: String, user_id: String) -> anyhow::Result<()> {
         return Ok(());
     } else {
         // No OAuth and no tokens - try unauthenticated
-        McpClient::new_with_config(server.clone())
+        McpClient::new_with_name(&server.name, &server.url)
     };
 
     // Test connection

src/cli/status.rs

@@ -8,9 +8,35 @@ use std::path::PathBuf;
 use crate::bootstrap::ironclaw_base_dir;
 use crate::settings::Settings;
 
+/// Load settings from JSON and TOML config files, matching the runtime
+/// priority: TOML overlay > settings.json > defaults.
+///
+/// This mirrors the loading chain in `Config::from_env_with_toml()` but
+/// without resolving the full `Config` (which requires async + secrets).
+fn load_settings() -> Settings {
+    load_settings_from(&Settings::default_path(), &Settings::default_toml_path())
+}
+
+/// Inner implementation with injectable paths (testable).
+fn load_settings_from(json_path: &std::path::Path, toml_path: &std::path::Path) -> Settings {
+    let mut settings = Settings::load_from(json_path);
+
+    match Settings::load_toml(toml_path) {
+        Ok(Some(toml_settings)) => {
+            settings.merge_from(&toml_settings);
+        }
+        Ok(None) => {} // File not found — fine for default path
+        Err(e) => {
+            eprintln!("Warning: failed to parse {}: {}", toml_path.display(), e);
+        }
+    }
+
+    settings
+}
+
 /// Run the status command, printing system health info.
 pub async fn run_status_command() -> anyhow::Result<()> {
-    let settings = Settings::default();
+    let settings = load_settings();
 
     println!("IronClaw Status");
     println!("===============\n");
@@ -209,3 +235,99 @@ fn default_tools_dir() -> PathBuf {
 fn default_channels_dir() -> PathBuf {
     ironclaw_base_dir().join("channels")
 }
+
+#[cfg(test)]
+mod tests {
+    use super::load_settings_from;
+
+    /// Regression test for #354: load_settings_from must read config.toml.
+    #[test]
+    fn reads_toml_heartbeat_enabled() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let json_path = dir.path().join("settings.json");
+        let toml_path = dir.path().join("config.toml");
+
+        // No JSON file — only TOML
+        std::fs::write(
+            &toml_path,
+            "[heartbeat]\nenabled = true\ninterval_secs = 600",
+        )
+        .expect("write toml");
+
+        let settings = load_settings_from(&json_path, &toml_path);
+        assert!(settings.heartbeat.enabled);
+        assert_eq!(settings.heartbeat.interval_secs, 600);
+    }
+
+    /// Without any config files, defaults are returned.
+    #[test]
+    fn defaults_without_config_files() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let settings = load_settings_from(
+            &dir.path().join("nonexistent.json"),
+            &dir.path().join("nonexistent.toml"),
+        );
+        assert!(!settings.heartbeat.enabled);
+    }
+
+    /// settings.json is respected.
+    #[test]
+    fn reads_json_heartbeat_enabled() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let json_path = dir.path().join("settings.json");
+        let toml_path = dir.path().join("nonexistent.toml");
+
+        std::fs::write(
+            &json_path,
+            r#"{"heartbeat":{"enabled":true,"interval_secs":900}}"#,
+        )
+        .expect("write json");
+
+        let settings = load_settings_from(&json_path, &toml_path);
+        assert!(settings.heartbeat.enabled);
+        assert_eq!(settings.heartbeat.interval_secs, 900);
+    }
+
+    /// TOML overlay wins over JSON settings.
+    #[test]
+    fn toml_overlay_wins_over_json() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let json_path = dir.path().join("settings.json");
+        let toml_path = dir.path().join("config.toml");
+
+        std::fs::write(
+            &json_path,
+            r#"{"heartbeat":{"enabled":false,"interval_secs":100}}"#,
+        )
+        .expect("write json");
+        std::fs::write(
+            &toml_path,
+            "[heartbeat]\nenabled = true\ninterval_secs = 200",
+        )
+        .expect("write toml");
+
+        let settings = load_settings_from(&json_path, &toml_path);
+        assert!(settings.heartbeat.enabled);
+        assert_eq!(settings.heartbeat.interval_secs, 200);
+    }
+
+    /// Invalid TOML is warned but doesn't crash; falls back to JSON/defaults.
+    #[test]
+    fn invalid_toml_falls_back_gracefully() {
+        let dir = tempfile::tempdir().expect("tempdir");
+        let json_path = dir.path().join("settings.json");
+        let toml_path = dir.path().join("config.toml");
+
+        std::fs::write(
+            &json_path,
+            r#"{"heartbeat":{"enabled":true,"interval_secs":500}}"#,
+        )
+        .expect("write json");
+        std::fs::write(&toml_path, "this is not valid toml [[[").expect("write bad toml");
+
+        let settings = load_settings_from(&json_path, &toml_path);
+        // Should fall back to JSON values, not crash
+        assert!(settings.heartbeat.enabled);
+        assert_eq!(settings.heartbeat.interval_secs, 500);
+    }
+}

src/config/agent.rs

@@ -27,6 +27,8 @@ pub struct AgentConfig {
     pub max_tool_iterations: usize,
     /// When true, skip tool approval checks entirely. For benchmarks/CI.
     pub auto_approve_tools: bool,
+    /// Default timezone for new sessions (IANA name, e.g. "America/New_York").
+    pub default_timezone: String,
 }
 
 impl AgentConfig {
@@ -47,6 +49,7 @@ impl AgentConfig {
             max_actions_per_hour: None,
             max_tool_iterations: 10,
             auto_approve_tools: true,
+            default_timezone: "UTC".to_string(),
         }
     }
 
@@ -89,6 +92,40 @@ impl AgentConfig {
                 "AGENT_AUTO_APPROVE_TOOLS",
                 settings.agent.auto_approve_tools,
             )?,
+            default_timezone: {
+                let tz: String = parse_optional_env(
+                    "DEFAULT_TIMEZONE",
+                    settings.agent.default_timezone.clone(),
+                )?;
+                if crate::timezone::parse_timezone(&tz).is_none() {
+                    return Err(ConfigError::InvalidValue {
+                        key: "DEFAULT_TIMEZONE".into(),
+                        message: format!("invalid IANA timezone: '{tz}'"),
+                    });
+                }
+                tz
+            },
         })
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_default_timezone_rejects_invalid() {
+        let mut settings = Settings::default();
+        settings.agent.default_timezone = "Fake/Zone".to_string();
+
+        let result = AgentConfig::resolve(&settings);
+        assert!(result.is_err(), "invalid IANA timezone should be rejected");
+    }
+
+    #[test]
+    fn test_default_timezone_accepts_valid() {
+        let settings = Settings::default(); // default is "UTC"
+        let config = AgentConfig::resolve(&settings).expect("resolve");
+        assert_eq!(config.default_timezone, "UTC");
+    }
+}

src/config/database.rs

@@ -82,6 +82,31 @@ impl std::str::FromStr for SslMode {
     }
 }
 
+/// Which vector store backend to use for workspace semantic search.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
+pub enum VectorBackend {
+    /// Use the database's built-in vector support (pgvector or libsql_vector_idx).
+    #[default]
+    Builtin,
+    /// Use LanceDB as an external vector store (requires `lancedb` feature).
+    LanceDb,
+}
+
+impl std::str::FromStr for VectorBackend {
+    type Err = String;
+
+    fn from_str(s: &str) -> Result<Self, Self::Err> {
+        match s.to_lowercase().as_str() {
+            "" | "builtin" | "pgvector" | "libsql" => Ok(Self::Builtin),
+            "lancedb" | "lance" => Ok(Self::LanceDb),
+            _ => Err(format!(
+                "invalid vector backend '{}', expected 'builtin' or 'lancedb'",
+                s
+            )),
+        }
+    }
+}
+
 /// Database configuration.
 #[derive(Debug, Clone)]
 pub struct DatabaseConfig {
@@ -101,6 +126,12 @@ pub struct DatabaseConfig {
     pub libsql_url: Option<String>,
     /// Turso auth token (required when libsql_url is set).
     pub libsql_auth_token: Option<SecretString>,
+
+    // -- Vector store fields --
+    /// Which vector store to use for workspace semantic search (default: Builtin).
+    pub vector_backend: VectorBackend,
+    /// Path to LanceDB directory (default: ~/.ironclaw/lancedb when vector_backend is LanceDb).
+    pub lancedb_path: Option<PathBuf>,
 }
 
 impl DatabaseConfig {
@@ -159,6 +190,25 @@ impl DatabaseConfig {
             });
         }
 
+        let vector_backend: VectorBackend = if let Some(s) = optional_env("VECTOR_BACKEND")? {
+            s.parse().map_err(|e| ConfigError::InvalidValue {
+                key: "VECTOR_BACKEND".to_string(),
+                message: e,
+            })?
+        } else {
+            VectorBackend::default()
+        };
+
+        let lancedb_path = optional_env("LANCEDB_PATH")?
+            .map(PathBuf::from)
+            .or_else(|| {
+                if vector_backend == VectorBackend::LanceDb {
+                    Some(default_lancedb_path())
+                } else {
+                    None
+                }
+            });
+
         Ok(Self {
             backend,
             url: SecretString::from(url),
@@ -167,6 +217,8 @@ impl DatabaseConfig {
             libsql_path,
             libsql_url,
             libsql_auth_token,
+            vector_backend,
+            lancedb_path,
         })
     }
 
@@ -195,6 +247,11 @@ pub fn default_libsql_path() -> PathBuf {
     ironclaw_base_dir().join("ironclaw.db")
 }
 
+/// Default LanceDB directory (~/.ironclaw/lancedb).
+pub fn default_lancedb_path() -> PathBuf {
+    ironclaw_base_dir().join("lancedb")
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -224,4 +281,39 @@ mod tests {
     fn ssl_mode_parse_invalid() {
         assert!("invalid".parse::<SslMode>().is_err());
     }
+
+    #[test]
+    fn vector_backend_parse() {
+        assert_eq!(
+            "builtin".parse::<VectorBackend>().unwrap(),
+            VectorBackend::Builtin
+        );
+        assert_eq!(
+            "pgvector".parse::<VectorBackend>().unwrap(),
+            VectorBackend::Builtin
+        );
+        assert_eq!(
+            "libsql".parse::<VectorBackend>().unwrap(),
+            VectorBackend::Builtin
+        );
+        assert_eq!("".parse::<VectorBackend>().unwrap(), VectorBackend::Builtin);
+
+        assert_eq!(
+            "lancedb".parse::<VectorBackend>().unwrap(),
+            VectorBackend::LanceDb
+        );
+        assert_eq!(
+            "lance".parse::<VectorBackend>().unwrap(),
+            VectorBackend::LanceDb
+        );
+
+        assert!("invalid".parse::<VectorBackend>().is_err());
+    }
+
+    #[test]
+    fn default_lancedb_path_under_ironclaw() {
+        let path = super::default_lancedb_path();
+        assert!(path.to_string_lossy().contains("ironclaw"));
+        assert!(path.to_string_lossy().ends_with("lancedb"));
+    }
 }

src/config/heartbeat.rs

@@ -1,4 +1,4 @@
-use crate::config::helpers::{optional_env, parse_bool_env, parse_optional_env};
+use crate::config::helpers::{optional_env, parse_bool_env, parse_option_env, parse_optional_env};
 use crate::error::ConfigError;
 use crate::settings::Settings;
 
@@ -13,6 +13,12 @@ pub struct HeartbeatConfig {
     pub notify_channel: Option<String>,
     /// User ID to notify on heartbeat findings.
     pub notify_user: Option<String>,
+    /// Hour (0-23) when quiet hours start.
+    pub quiet_hours_start: Option<u32>,
+    /// Hour (0-23) when quiet hours end.
+    pub quiet_hours_end: Option<u32>,
+    /// Timezone for quiet hours evaluation (IANA name).
+    pub timezone: Option<String>,
 }
 
 impl Default for HeartbeatConfig {
@@ -22,6 +28,9 @@ impl Default for HeartbeatConfig {
             interval_secs: 1800, // 30 minutes
             notify_channel: None,
             notify_user: None,
+            quiet_hours_start: None,
+            quiet_hours_end: None,
+            timezone: None,
         }
     }
 }
@@ -38,6 +47,98 @@ impl HeartbeatConfig {
                 .or_else(|| settings.heartbeat.notify_channel.clone()),
             notify_user: optional_env("HEARTBEAT_NOTIFY_USER")?
                 .or_else(|| settings.heartbeat.notify_user.clone()),
+            quiet_hours_start: parse_option_env::<u32>("HEARTBEAT_QUIET_START")?
+                .or(settings.heartbeat.quiet_hours_start)
+                .map(|h| {
+                    if h > 23 {
+                        return Err(ConfigError::InvalidValue {
+                            key: "HEARTBEAT_QUIET_START".into(),
+                            message: "must be 0-23".into(),
+                        });
+                    }
+                    Ok(h)
+                })
+                .transpose()?,
+            quiet_hours_end: parse_option_env::<u32>("HEARTBEAT_QUIET_END")?
+                .or(settings.heartbeat.quiet_hours_end)
+                .map(|h| {
+                    if h > 23 {
+                        return Err(ConfigError::InvalidValue {
+                            key: "HEARTBEAT_QUIET_END".into(),
+                            message: "must be 0-23".into(),
+                        });
+                    }
+                    Ok(h)
+                })
+                .transpose()?,
+            timezone: {
+                let tz = optional_env("HEARTBEAT_TIMEZONE")?
+                    .or_else(|| settings.heartbeat.timezone.clone());
+                if let Some(ref tz_str) = tz
+                    && crate::timezone::parse_timezone(tz_str).is_none()
+                {
+                    return Err(ConfigError::InvalidValue {
+                        key: "HEARTBEAT_TIMEZONE".into(),
+                        message: format!("invalid IANA timezone: '{tz_str}'"),
+                    });
+                }
+                tz
+            },
         })
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_quiet_hours_settings_fallback() {
+        // When env vars are not set, settings values should be used
+        let mut settings = Settings::default();
+        settings.heartbeat.quiet_hours_start = Some(22);
+        settings.heartbeat.quiet_hours_end = Some(6);
+
+        let config = HeartbeatConfig::resolve(&settings).expect("resolve");
+        assert_eq!(config.quiet_hours_start, Some(22));
+        assert_eq!(config.quiet_hours_end, Some(6));
+    }
+
+    #[test]
+    fn test_quiet_hours_rejects_invalid_hour() {
+        let mut settings = Settings::default();
+        settings.heartbeat.quiet_hours_start = Some(24);
+
+        let result = HeartbeatConfig::resolve(&settings);
+        assert!(result.is_err());
+    }
+
+    #[test]
+    fn test_quiet_hours_accepts_boundary_values() {
+        let mut settings = Settings::default();
+        settings.heartbeat.quiet_hours_start = Some(0);
+        settings.heartbeat.quiet_hours_end = Some(23);
+
+        let config = HeartbeatConfig::resolve(&settings).expect("resolve");
+        assert_eq!(config.quiet_hours_start, Some(0));
+        assert_eq!(config.quiet_hours_end, Some(23));
+    }
+
+    #[test]
+    fn test_heartbeat_timezone_rejects_invalid() {
+        let mut settings = Settings::default();
+        settings.heartbeat.timezone = Some("Fake/Zone".to_string());
+
+        let result = HeartbeatConfig::resolve(&settings);
+        assert!(result.is_err(), "invalid IANA timezone should be rejected");
+    }
+
+    #[test]
+    fn test_heartbeat_timezone_accepts_valid() {
+        let mut settings = Settings::default();
+        settings.heartbeat.timezone = Some("America/New_York".to_string());
+
+        let config = HeartbeatConfig::resolve(&settings).expect("resolve");
+        assert_eq!(config.timezone.as_deref(), Some("America/New_York"));
+    }
+}

src/config/llm.rs

@@ -103,6 +103,10 @@ pub struct LlmConfig {
     /// Resolved provider config for registry-based providers.
     /// `None` when backend is "nearai".
     pub provider: Option<RegistryProviderConfig>,
+    /// HTTP request timeout in seconds for LLM API calls.
+    /// Default: 120. Increase for local LLMs (Ollama, vLLM, LM Studio) that
+    /// need more time for prompt evaluation on consumer hardware.
+    pub request_timeout_secs: u64,
 }
 
 /// NEAR AI configuration.
@@ -165,6 +169,7 @@ impl LlmConfig {
                 smart_routing_cascade: false,
             },
             provider: None,
+            request_timeout_secs: 120,
         }
     }
 
@@ -254,6 +259,8 @@ impl LlmConfig {
             )?)
         };
 
+        let request_timeout_secs = parse_optional_env("LLM_REQUEST_TIMEOUT_SECS", 120)?;
+
         Ok(Self {
             backend: if is_nearai {
                 "nearai".to_string()
@@ -265,6 +272,7 @@ impl LlmConfig {
             session,
             nearai,
             provider,
+            request_timeout_secs,
         })
     }
 
@@ -1016,4 +1024,30 @@ mod tests {
             assert_eq!(parsed, variant, "round-trip failed for {s}");
         }
     }
+
+    #[test]
+    fn test_request_timeout_defaults_to_120() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::remove_var("LLM_REQUEST_TIMEOUT_SECS");
+        }
+        let config = LlmConfig::resolve(&Settings::default()).expect("resolve");
+        assert_eq!(config.request_timeout_secs, 120);
+    }
+
+    #[test]
+    fn test_request_timeout_configurable() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("LLM_REQUEST_TIMEOUT_SECS", "300");
+        }
+        let config = LlmConfig::resolve(&Settings::default()).expect("resolve");
+        assert_eq!(config.request_timeout_secs, 300);
+        // SAFETY: Cleanup
+        unsafe {
+            std::env::remove_var("LLM_REQUEST_TIMEOUT_SECS");
+        }
+    }
 }

src/config/mod.rs

@@ -33,7 +33,10 @@ use crate::settings::Settings;
 pub use self::agent::AgentConfig;
 pub use self::builder::BuilderModeConfig;
 pub use self::channels::{ChannelsConfig, CliConfig, GatewayConfig, HttpConfig, SignalConfig};
-pub use self::database::{DatabaseBackend, DatabaseConfig, SslMode, default_libsql_path};
+pub use self::database::{
+    DatabaseBackend, DatabaseConfig, SslMode, VectorBackend, default_lancedb_path,
+    default_libsql_path,
+};
 pub use self::embeddings::EmbeddingsConfig;
 pub use self::heartbeat::HeartbeatConfig;
 pub use self::hygiene::HygieneConfig;
@@ -107,6 +110,8 @@ impl Config {
                 libsql_path: Some(libsql_path),
                 libsql_url: None,
                 libsql_auth_token: None,
+                vector_backend: VectorBackend::default(),
+                lancedb_path: None,
             },
             llm: LlmConfig::for_testing(),
             embeddings: EmbeddingsConfig::default(),
@@ -257,6 +262,32 @@ impl Config {
         Ok(())
     }
 
+    /// Re-resolve only the LLM config after credential injection.
+    ///
+    /// Called by `AppBuilder::init_secrets()` after injecting API keys into
+    /// the env overlay. Only rebuilds `self.llm` — all other config fields
+    /// are unaffected, preserving values from the initial config load (or
+    /// from `Config::for_testing()` in test mode).
+    pub async fn re_resolve_llm(
+        &mut self,
+        store: Option<&(dyn crate::db::SettingsStore + Sync)>,
+        user_id: &str,
+        toml_path: Option<&std::path::Path>,
+    ) -> Result<(), ConfigError> {
+        let settings = if let Some(store) = store {
+            let mut s = match store.get_all_settings(user_id).await {
+                Ok(map) => Settings::from_db_map(&map),
+                Err(_) => Settings::default(),
+            };
+            Self::apply_toml_overlay(&mut s, toml_path)?;
+            s
+        } else {
+            Settings::default()
+        };
+        self.llm = LlmConfig::resolve(&settings)?;
+        Ok(())
+    }
+
     /// Build config from settings (shared by from_env and from_db).
     async fn build(settings: &Settings) -> Result<Self, ConfigError> {
         Ok(Self {

src/context/state.rs

@@ -164,6 +164,8 @@ pub struct JobContext {
     /// previous results by ID via `$tool_call_id` parameter syntax.
     #[serde(skip)]
     pub tool_output_stash: Arc<tokio::sync::RwLock<HashMap<String, String>>>,
+    /// User's preferred timezone (IANA name, e.g. "America/New_York"). Defaults to "UTC".
+    pub user_timezone: String,
 }
 
 impl JobContext {
@@ -203,9 +205,16 @@ impl JobContext {
             http_interceptor: None,
             metadata: serde_json::Value::Null,
             tool_output_stash: Arc::new(tokio::sync::RwLock::new(HashMap::new())),
+            user_timezone: "UTC".to_string(),
         }
     }
 
+    /// Set the user timezone on this context.
+    pub fn with_timezone(mut self, tz: impl Into<String>) -> Self {
+        self.user_timezone = tz.into();
+        self
+    }
+
     /// Transition to a new state.
     pub fn transition_to(
         &mut self,

src/db/libsql/jobs.rs

@@ -121,6 +121,9 @@ impl JobStore for LibSqlBackend {
                     tool_output_stash: std::sync::Arc::new(tokio::sync::RwLock::new(
                         std::collections::HashMap::new(),
                     )),
+                    // TODO(#661): persist user_timezone in agent_jobs table so
+                    // background/routine jobs retain the session's timezone context.
+                    user_timezone: "UTC".to_string(),
                 }))
             }
             None => Ok(None),

src/evaluation/success.rs

@@ -1,13 +1,10 @@
 //! Success evaluation for jobs.
 
-use std::sync::Arc;
-
 use async_trait::async_trait;
 use serde::{Deserialize, Serialize};
 
 use crate::context::{ActionRecord, JobContext};
 use crate::error::EvaluationError;
-use crate::llm::LlmProvider;
 
 /// Result of evaluating job success.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -64,233 +61,132 @@ pub trait SuccessEvaluator: Send + Sync {
     ) -> Result<EvaluationResult, EvaluationError>;
 }
 
-/// Rule-based success evaluator.
-pub struct RuleBasedEvaluator {
-    /// Minimum success rate for actions.
-    min_action_success_rate: f64,
-    /// Maximum allowed failures.
-    max_failures: u32,
-}
-
-impl RuleBasedEvaluator {
-    /// Create a new rule-based evaluator.
-    pub fn new() -> Self {
-        Self {
-            min_action_success_rate: 0.8,
-            max_failures: 3,
-        }
-    }
-
-    /// Set minimum action success rate.
-    #[allow(dead_code)] // Public API for configuring evaluation threshold
-    pub fn with_min_success_rate(mut self, rate: f64) -> Self {
-        self.min_action_success_rate = rate;
-        self
-    }
-
-    /// Set maximum failures.
-    #[allow(dead_code)] // Public API for configuring failure tolerance
-    pub fn with_max_failures(mut self, max: u32) -> Self {
-        self.max_failures = max;
-        self
-    }
-}
-
-impl Default for RuleBasedEvaluator {
-    fn default() -> Self {
-        Self::new()
-    }
-}
-
-#[async_trait]
-impl SuccessEvaluator for RuleBasedEvaluator {
-    async fn evaluate(
-        &self,
-        job: &JobContext,
-        actions: &[ActionRecord],
-        _output: Option<&str>,
-    ) -> Result<EvaluationResult, EvaluationError> {
-        let mut issues = Vec::new();
-
-        // Check if there were any actions
-        if actions.is_empty() {
-            return Ok(EvaluationResult::failure(
-                "No actions were taken",
-                vec!["No actions recorded".to_string()],
-            ));
-        }
-
-        // Calculate action success rate
-        let successful = actions.iter().filter(|a| a.success).count();
-        let total = actions.len();
-        let success_rate = successful as f64 / total as f64;
-
-        if success_rate < self.min_action_success_rate {
-            issues.push(format!(
-                "Action success rate {:.1}% below threshold {:.1}%",
-                success_rate * 100.0,
-                self.min_action_success_rate * 100.0
-            ));
-        }
-
-        // Count failures
-        let failures = actions.iter().filter(|a| !a.success).count() as u32;
-        if failures > self.max_failures {
-            issues.push(format!(
-                "Too many failures: {} (max {})",
-                failures, self.max_failures
-            ));
-        }
-
-        // Check for critical errors
-        for action in actions.iter().filter(|a| !a.success) {
-            if let Some(ref error) = action.error
-                && (error.to_lowercase().contains("critical")
-                    || error.to_lowercase().contains("fatal"))
-            {
-                issues.push(format!("Critical error in {}: {}", action.tool_name, error));
-            }
-        }
-
-        // Check job state
-        if job.state != crate::context::JobState::Completed
-            && job.state != crate::context::JobState::Submitted
-        {
-            issues.push(format!("Job not in completed state: {:?}", job.state));
-        }
-
-        // Calculate quality score
-        let quality_score = if issues.is_empty() {
-            let base_score = (success_rate * 80.0) as u32;
-            let completion_bonus = if job.state == crate::context::JobState::Completed {
-                20
-            } else {
-                0
-            };
-            (base_score + completion_bonus).min(100)
-        } else {
-            ((success_rate * 50.0) as u32).min(50)
-        };
-
-        if issues.is_empty() {
-            Ok(EvaluationResult::success(
-                format!(
-                    "Job completed successfully with {}/{} actions succeeding ({:.1}%)",
-                    successful,
-                    total,
-                    success_rate * 100.0
-                ),
-                quality_score,
-            ))
-        } else {
-            Ok(EvaluationResult {
-                success: false,
-                confidence: 0.85,
-                reasoning: format!("Job had {} issues", issues.len()),
-                issues,
-                suggestions: vec![
-                    "Review failed actions for common patterns".to_string(),
-                    "Consider adjusting retry logic".to_string(),
-                ],
-                quality_score,
-            })
-        }
-    }
-}
-
-/// LLM-based success evaluator for more nuanced evaluation.
-pub struct LlmEvaluator {
-    llm: Arc<dyn LlmProvider>,
-}
-
-impl LlmEvaluator {
-    /// Create a new LLM-based evaluator.
-    #[allow(dead_code)] // Public API for LLM-based evaluation
-    pub fn new(llm: Arc<dyn LlmProvider>) -> Self {
-        Self { llm }
-    }
-}
-
-#[async_trait]
-impl SuccessEvaluator for LlmEvaluator {
-    async fn evaluate(
-        &self,
-        job: &JobContext,
-        actions: &[ActionRecord],
-        output: Option<&str>,
-    ) -> Result<EvaluationResult, EvaluationError> {
-        // Build evaluation prompt
-        let actions_summary: Vec<String> = actions
-            .iter()
-            .map(|a| {
-                format!(
-                    "- {}: {} ({})",
-                    a.tool_name,
-                    if a.success { "success" } else { "failed" },
-                    a.error.as_deref().unwrap_or("ok")
-                )
-            })
-            .collect();
-
-        let prompt = format!(
-            r#"Evaluate if this job was completed successfully.
-
-Job: {}
-Description: {}
-State: {:?}
-
-Actions taken:
-{}
-
-{}
-
-Respond in JSON format:
-{{
-    "success": true/false,
-    "confidence": 0.0-1.0,
-    "reasoning": "...",
-    "issues": ["..."],
-    "suggestions": ["..."],
-    "quality_score": 0-100
-}}"#,
-            job.title,
-            job.description,
-            job.state,
-            actions_summary.join("\n"),
-            output
-                .map(|o| format!("Output:\n{}", o))
-                .unwrap_or_default()
-        );
-
-        let request =
-            crate::llm::CompletionRequest::new(vec![crate::llm::ChatMessage::user(prompt)])
-                .with_max_tokens(1024)
-                .with_temperature(0.1);
-
-        let response = self
-            .llm
-            .complete(request)
-            .await
-            .map_err(|e| EvaluationError::Failed {
-                job_id: job.job_id,
-                reason: e.to_string(),
-            })?;
-
-        // Parse the response
-        let result: EvaluationResult =
-            serde_json::from_str(&response.content).map_err(|e| EvaluationError::Failed {
-                job_id: job.job_id,
-                reason: format!("Failed to parse LLM evaluation: {}", e),
-            })?;
-
-        Ok(result)
-    }
-}
-
 #[cfg(test)]
 mod tests {
     use super::*;
-    use crate::context::JobContext;
+    use crate::context::{ActionRecord, JobContext};
+    use crate::error::EvaluationError;
+
+    /// Rule-based success evaluator (test-only; no production callers).
+    struct RuleBasedEvaluator {
+        min_action_success_rate: f64,
+        max_failures: u32,
+    }
+
+    impl RuleBasedEvaluator {
+        fn new() -> Self {
+            Self {
+                min_action_success_rate: 0.8,
+                max_failures: 3,
+            }
+        }
+
+        fn with_min_success_rate(mut self, rate: f64) -> Self {
+            self.min_action_success_rate = rate;
+            self
+        }
+
+        fn with_max_failures(mut self, max: u32) -> Self {
+            self.max_failures = max;
+            self
+        }
+    }
+
+    impl Default for RuleBasedEvaluator {
+        fn default() -> Self {
+            Self::new()
+        }
+    }
+
+    #[async_trait::async_trait]
+    impl SuccessEvaluator for RuleBasedEvaluator {
+        async fn evaluate(
+            &self,
+            job: &JobContext,
+            actions: &[ActionRecord],
+            _output: Option<&str>,
+        ) -> Result<EvaluationResult, EvaluationError> {
+            let mut issues = Vec::new();
+
+            if actions.is_empty() {
+                return Ok(EvaluationResult::failure(
+                    "No actions were taken",
+                    vec!["No actions recorded".to_string()],
+                ));
+            }
+
+            let successful = actions.iter().filter(|a| a.success).count();
+            let total = actions.len();
+            let success_rate = successful as f64 / total as f64;
+
+            if success_rate < self.min_action_success_rate {
+                issues.push(format!(
+                    "Action success rate {:.1}% below threshold {:.1}%",
+                    success_rate * 100.0,
+                    self.min_action_success_rate * 100.0
+                ));
+            }
+
+            let failures = actions.iter().filter(|a| !a.success).count() as u32;
+            if failures > self.max_failures {
+                issues.push(format!(
+                    "Too many failures: {} (max {})",
+                    failures, self.max_failures
+                ));
+            }
+
+            for action in actions.iter().filter(|a| !a.success) {
+                if let Some(ref error) = action.error
+                    && (error.to_lowercase().contains("critical")
+                        || error.to_lowercase().contains("fatal"))
+                {
+                    issues.push(format!("Critical error in {}: {}", action.tool_name, error));
+                }
+            }
+
+            if job.state != crate::context::JobState::Completed
+                && job.state != crate::context::JobState::Submitted
+            {
+                issues.push(format!("Job not in completed state: {:?}", job.state));
+            }
+
+            let quality_score = if issues.is_empty() {
+                let base_score = (success_rate * 80.0) as u32;
+                let completion_bonus = if job.state == crate::context::JobState::Completed {
+                    20
+                } else {
+                    0
+                };
+                (base_score + completion_bonus).min(100)
+            } else {
+                ((success_rate * 50.0) as u32).min(50)
+            };
+
+            if issues.is_empty() {
+                Ok(EvaluationResult::success(
+                    format!(
+                        "Job completed successfully with {}/{} actions succeeding ({:.1}%)",
+                        successful,
+                        total,
+                        success_rate * 100.0
+                    ),
+                    quality_score,
+                ))
+            } else {
+                Ok(EvaluationResult {
+                    success: false,
+                    confidence: 0.85,
+                    reasoning: format!("Job had {} issues", issues.len()),
+                    issues,
+                    suggestions: vec![
+                        "Review failed actions for common patterns".to_string(),
+                        "Consider adjusting retry logic".to_string(),
+                    ],
+                    quality_score,
+                })
+            }
+        }
+    }
 
     #[tokio::test]
     async fn test_rule_based_evaluator_success() {

src/extensions/manager.rs

@@ -1405,38 +1405,6 @@ impl ExtensionManager {
         Ok(())
     }
 
-    #[allow(dead_code)] // Used by upcoming hot-activation flow
-    async fn install_bundled_channel_from_artifacts(
-        &self,
-        name: &str,
-    ) -> Result<InstallResult, ExtensionError> {
-        // Check if already installed
-        let channel_wasm = self.wasm_channels_dir.join(format!("{}.wasm", name));
-        if channel_wasm.exists() {
-            return Err(ExtensionError::AlreadyInstalled(name.to_string()));
-        }
-
-        crate::channels::wasm::install_bundled_channel(name, &self.wasm_channels_dir, false)
-            .await
-            .map_err(ExtensionError::InstallFailed)?;
-
-        tracing::info!(
-            "Installed bundled channel '{}' to {}",
-            name,
-            self.wasm_channels_dir.display()
-        );
-
-        Ok(InstallResult {
-            name: name.to_string(),
-            kind: ExtensionKind::WasmChannel,
-            message: format!(
-                "Channel '{}' installed. \
-                 Run tool_auth('{}') to configure authentication, then activate.",
-                name, name,
-            ),
-        })
-    }
-
     /// Install a WASM extension from local build artifacts (WasmBuildable source).
     ///
     /// Resolves the build directory (relative to `CARGO_MANIFEST_DIR` or absolute),
@@ -2508,7 +2476,7 @@ impl ExtensionManager {
                 &self.user_id,
             )
         } else {
-            McpClient::new_with_config(server.clone())
+            McpClient::new_with_name(&server.name, &server.url)
         };
 
         // Try to list and create tools

src/history/store.rs

@@ -241,6 +241,9 @@ impl Store {
                     tool_output_stash: std::sync::Arc::new(tokio::sync::RwLock::new(
                         std::collections::HashMap::new(),
                     )),
+                    // TODO(#661): persist user_timezone in agent_jobs table so
+                    // background/routine jobs retain the session's timezone context.
+                    user_timezone: "UTC".to_string(),
                 }))
             }
             None => Ok(None),

src/lib.rs

@@ -66,6 +66,7 @@ pub mod service;
 pub mod settings;
 pub mod setup;
 pub mod skills;
+pub mod timezone;
 pub mod tools;
 pub mod tracing_fmt;
 pub mod transcription;

src/llm/mod.rs

@@ -58,8 +58,10 @@ pub fn create_llm_provider(
     config: &LlmConfig,
     session: Arc<SessionManager>,
 ) -> Result<Arc<dyn LlmProvider>, LlmError> {
+    let timeout = config.request_timeout_secs;
+
     if config.backend == "nearai" || config.backend == "near_ai" || config.backend == "near" {
-        return create_llm_provider_with_config(&config.nearai, session);
+        return create_llm_provider_with_config(&config.nearai, session, timeout);
     }
 
     let reg_config = config
@@ -79,6 +81,7 @@ pub fn create_llm_provider(
 pub fn create_llm_provider_with_config(
     config: &NearAiConfig,
     session: Arc<SessionManager>,
+    request_timeout_secs: u64,
 ) -> Result<Arc<dyn LlmProvider>, LlmError> {
     let auth_mode = if config.api_key.is_some() {
         "API key"
@@ -89,9 +92,14 @@ pub fn create_llm_provider_with_config(
         model = %config.model,
         base_url = %config.base_url,
         auth = auth_mode,
+        timeout_secs = request_timeout_secs,
         "Using NEAR AI (Chat Completions API)"
     );
-    Ok(Arc::new(NearAiChatProvider::new(config.clone(), session)?))
+    Ok(Arc::new(NearAiChatProvider::new_with_timeout(
+        config.clone(),
+        session,
+        request_timeout_secs,
+    )?))
 }
 
 /// Create a provider from a registry-resolved config.
@@ -365,7 +373,11 @@ pub fn build_provider_chain(
     let llm: Arc<dyn LlmProvider> = if let Some(ref cheap_model) = config.nearai.cheap_model {
         let mut cheap_config = config.nearai.clone();
         cheap_config.model = cheap_model.clone();
-        let cheap = create_llm_provider_with_config(&cheap_config, session.clone())?;
+        let cheap = create_llm_provider_with_config(
+            &cheap_config,
+            session.clone(),
+            config.request_timeout_secs,
+        )?;
         let cheap: Arc<dyn LlmProvider> = if retry_config.max_retries > 0 {
             Arc::new(RetryProvider::new(cheap, retry_config.clone()))
         } else {
@@ -397,7 +409,11 @@ pub fn build_provider_chain(
         }
         let mut fallback_config = config.nearai.clone();
         fallback_config.model = fallback_model.clone();
-        let fallback = create_llm_provider_with_config(&fallback_config, session.clone())?;
+        let fallback = create_llm_provider_with_config(
+            &fallback_config,
+            session.clone(),
+            config.request_timeout_secs,
+        )?;
         tracing::info!(
             primary = %llm.model_name(),
             fallback = %fallback.model_name(),
@@ -503,6 +519,7 @@ mod tests {
             session: SessionConfig::default(),
             nearai: test_nearai_config(),
             provider: None,
+            request_timeout_secs: 120,
         }
     }
 

src/llm/nearai_chat.rs

@@ -58,17 +58,28 @@ impl NearAiChatProvider {
     /// By default this enables tool-message flattening for compatibility with
     /// providers that reject `role: "tool"` messages.
     pub fn new(config: NearAiConfig, session: Arc<SessionManager>) -> Result<Self, LlmError> {
-        Self::new_with_flatten(config, session, true)
+        Self::new_with_options(config, session, true, 120)
     }
 
-    /// Create a chat completions provider with configurable tool-message flattening.
-    pub fn new_with_flatten(
+    /// Create a new provider with a custom request timeout.
+    pub fn new_with_timeout(
+        config: NearAiConfig,
+        session: Arc<SessionManager>,
+        request_timeout_secs: u64,
+    ) -> Result<Self, LlmError> {
+        Self::new_with_options(config, session, true, request_timeout_secs)
+    }
+
+    /// Create a chat completions provider with configurable tool-message flattening
+    /// and request timeout.
+    pub fn new_with_options(
         config: NearAiConfig,
         session: Arc<SessionManager>,
         flatten_tool_messages: bool,
+        request_timeout_secs: u64,
     ) -> Result<Self, LlmError> {
         let client = Client::builder()
-            .timeout(std::time::Duration::from_secs(120))
+            .timeout(std::time::Duration::from_secs(request_timeout_secs))
             .build()
             .map_err(|e| LlmError::RequestFailed {
                 provider: "nearai_chat".to_string(),

src/llm/reasoning.rs

@@ -11,7 +11,6 @@ use crate::llm::{
     ChatMessage, CompletionRequest, LlmProvider, Role, ToolCall, ToolCompletionRequest,
     ToolDefinition,
 };
-use crate::safety::SafetyLayer;
 
 /// Token the agent returns when it has nothing to say (e.g. in group chats).
 /// The dispatcher should check for this and suppress the message.
@@ -343,8 +342,6 @@ pub struct RespondOutput {
 /// Reasoning engine for the agent.
 pub struct Reasoning {
     llm: Arc<dyn LlmProvider>,
-    #[allow(dead_code)] // Will be used for sanitizing tool outputs
-    safety: Arc<SafetyLayer>,
     /// Optional workspace for loading identity/system prompts.
     workspace_system_prompt: Option<String>,
     /// Optional skill context block to inject into system prompt.
@@ -362,10 +359,9 @@ pub struct Reasoning {
 
 impl Reasoning {
     /// Create a new reasoning engine.
-    pub fn new(llm: Arc<dyn LlmProvider>, safety: Arc<SafetyLayer>) -> Self {
+    pub fn new(llm: Arc<dyn LlmProvider>) -> Self {
         Self {
             llm,
-            safety,
             workspace_system_prompt: None,
             skill_context: None,
             channel: None,
@@ -2117,15 +2113,9 @@ That's my plan."#;
     // ---- System prompt building tests (issue #565) ----
 
     fn make_test_reasoning() -> Reasoning {
-        use crate::config::SafetyConfig;
-        use crate::safety::SafetyLayer;
         use crate::testing::StubLlm;
         let llm = Arc::new(StubLlm::new("test"));
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
-        Reasoning::new(llm, safety)
+        Reasoning::new(llm)
     }
 
     #[test]

src/llm/session.rs

@@ -200,9 +200,10 @@ impl SessionManager {
 
         let status = response.status();
         let body = response.text().await.unwrap_or_default();
+        let preview = crate::agent::truncate_for_preview(&body, 200);
         Err(LlmError::SessionRenewalFailed {
             provider: "nearai".to_string(),
-            reason: format!("Validation failed: HTTP {}: {}", status, body),
+            reason: format!("Validation failed: HTTP {status}: {preview}"),
         })
     }
 

src/main.rs

@@ -145,6 +145,24 @@ async fn async_main() -> anyhow::Result<()> {
         }
     }
 
+    // ── PID lock (prevent multiple instances) ────────────────────────
+    let _pid_lock = match ironclaw::bootstrap::PidLock::acquire() {
+        Ok(lock) => Some(lock),
+        Err(ironclaw::bootstrap::PidLockError::AlreadyRunning { pid }) => {
+            anyhow::bail!(
+                "Another IronClaw instance is already running (PID {}). \
+                 If this is incorrect, remove the stale PID file: {}",
+                pid,
+                ironclaw::bootstrap::pid_lock_path().display()
+            );
+        }
+        Err(e) => {
+            eprintln!("Warning: Could not acquire PID lock: {}", e);
+            eprintln!("Continuing without PID lock protection.");
+            None
+        }
+    };
+
     // ── Agent startup ──────────────────────────────────────────────────
 
     // Enhanced first-run detection
@@ -166,13 +184,12 @@ async fn async_main() -> anyhow::Result<()> {
     let config = match Config::from_env_with_toml(toml_path).await {
         Ok(c) => c,
         Err(ironclaw::error::ConfigError::MissingRequired { key, hint }) => {
-            eprintln!("Configuration error: Missing required setting '{}'", key);
-            eprintln!("  {}", hint);
-            eprintln!();
-            eprintln!(
-                "Run 'ironclaw onboard' to configure, or set the required environment variables."
+            anyhow::bail!(
+                "Configuration error: Missing required setting '{}'. {}. \
+                 Run 'ironclaw onboard' to configure, or set the required environment variables.",
+                key,
+                hint
             );
-            std::process::exit(1);
         }
         Err(e) => return Err(e.into()),
     };

src/settings.rs

@@ -42,6 +42,10 @@ pub struct Settings {
     #[serde(default)]
     pub secrets_master_key_source: KeySource,
 
+    /// Generated master key hex (env var mode only, written to .env by wizard).
+    #[serde(default, skip_serializing)]
+    pub secrets_master_key_hex: Option<String>,
+
     // === Step 3: Inference Provider ===
     /// LLM backend: "nearai", "anthropic", "openai", "ollama", "openai_compatible".
     #[serde(default)]
@@ -291,6 +295,18 @@ pub struct HeartbeatSettings {
     /// User ID to notify on heartbeat findings.
     #[serde(default)]
     pub notify_user: Option<String>,
+
+    /// Hour (0-23) when quiet hours start (heartbeat skipped).
+    #[serde(default)]
+    pub quiet_hours_start: Option<u32>,
+
+    /// Hour (0-23) when quiet hours end (heartbeat resumes).
+    #[serde(default)]
+    pub quiet_hours_end: Option<u32>,
+
+    /// Timezone for quiet hours evaluation (IANA name, e.g. "America/New_York").
+    #[serde(default)]
+    pub timezone: Option<String>,
 }
 
 fn default_heartbeat_interval() -> u64 {
@@ -304,6 +320,9 @@ impl Default for HeartbeatSettings {
             interval_secs: default_heartbeat_interval(),
             notify_channel: None,
             notify_user: None,
+            quiet_hours_start: None,
+            quiet_hours_end: None,
+            timezone: None,
         }
     }
 }
@@ -351,6 +370,10 @@ pub struct AgentSettings {
     /// When true, skip tool approval checks entirely. For benchmarks/CI.
     #[serde(default)]
     pub auto_approve_tools: bool,
+
+    /// Default timezone for new sessions (IANA name, e.g. "America/New_York").
+    #[serde(default = "default_timezone")]
+    pub default_timezone: String,
 }
 
 fn default_agent_name() -> String {
@@ -385,6 +408,10 @@ fn default_max_tool_iterations() -> usize {
     50
 }
 
+fn default_timezone() -> String {
+    "UTC".to_string()
+}
+
 fn default_true() -> bool {
     true
 }
@@ -402,6 +429,7 @@ impl Default for AgentSettings {
             session_idle_timeout_secs: default_session_idle_timeout(),
             max_tool_iterations: default_max_tool_iterations(),
             auto_approve_tools: false,
+            default_timezone: default_timezone(),
         }
     }
 }
@@ -1174,6 +1202,31 @@ mod tests {
         assert_eq!(loaded.heartbeat.interval_secs, 900);
     }
 
+    /// Regression test: /model command must persist selected_model to TOML config.
+    /// Prior to the fix, `set_model()` only changed the in-memory provider and the
+    /// choice was lost on restart.
+    #[test]
+    fn toml_selected_model_update_persists() {
+        let dir = tempfile::tempdir().unwrap();
+        let path = dir.path().join("config.toml");
+
+        // Start with a config that has a different model.
+        let settings = Settings {
+            selected_model: Some("old-model".to_string()),
+            ..Default::default()
+        };
+        settings.save_toml(&path).unwrap();
+
+        // Simulate what persist_selected_model does: load, update, save.
+        let mut loaded = Settings::load_toml(&path).unwrap().unwrap();
+        loaded.selected_model = Some("new-model".to_string());
+        loaded.save_toml(&path).unwrap();
+
+        // Verify the change survived a reload.
+        let reloaded = Settings::load_toml(&path).unwrap().unwrap();
+        assert_eq!(reloaded.selected_model, Some("new-model".to_string()));
+    }
+
     #[test]
     fn toml_missing_file_returns_none() {
         let result = Settings::load_toml(std::path::Path::new("/tmp/nonexistent_config.toml"));

src/setup/wizard.rs

@@ -769,13 +769,28 @@ impl SetupWizard {
                 print_success("Master key generated and stored in OS keychain");
             }
             1 => {
-                // Env var mode
-                print_info("Generate a key and add it to your environment:");
+                // Env var mode — generate key, init crypto, and persist to .env
                 let key_hex = crate::secrets::keychain::generate_master_key_hex();
+
+                // Initialize crypto so subsequent wizard steps (channel setup,
+                // API key storage) can encrypt secrets immediately.
+                self.secrets_crypto = Some(Arc::new(
+                    SecretsCrypto::new(SecretString::from(key_hex.clone()))
+                        .map_err(|e| SetupError::Config(e.to_string()))?,
+                ));
+
+                // Make visible to optional_env() for any subsequent config resolution.
+                crate::config::inject_single_var("SECRETS_MASTER_KEY", &key_hex);
+
+                // Store hex for write_bootstrap_env to persist to ~/.ironclaw/.env.
+                self.settings.secrets_master_key_hex = Some(key_hex.clone());
+
                 println!();
-                println!("  export SECRETS_MASTER_KEY={}", key_hex);
+                print_info("Master key generated and will be saved to ~/.ironclaw/.env");
                 println!();
-                print_info("Add this to your shell profile or .env file.");
+                println!("  SECRETS_MASTER_KEY={}", key_hex);
+                println!();
+                print_info("You can also copy this to another .env file or CI secrets.");
 
                 self.settings.secrets_master_key_source = KeySource::Env;
                 print_success("Configured for environment variable");
@@ -1022,10 +1037,11 @@ impl SetupWizard {
 
     /// Anthropic OAuth setup: extract token from `claude login` credentials.
     async fn setup_anthropic_oauth(&mut self) -> Result<(), SetupError> {
-        self.settings.llm_backend = Some("anthropic".to_string());
-        if self.settings.selected_model.is_some() {
+        // Clear model only when switching providers (old model may be invalid)
+        if self.settings.llm_backend.as_deref() != Some("anthropic") {
             self.settings.selected_model = None;
         }
+        self.settings.llm_backend = Some("anthropic".to_string());
 
         // Try to extract existing OAuth token from Claude Code credentials
         if let Some(token) = crate::config::ClaudeCodeConfig::extract_oauth_token() {
@@ -1119,10 +1135,11 @@ impl SetupWizard {
             other => other,
         });
 
-        self.settings.llm_backend = Some(backend.to_string());
-        if self.settings.selected_model.is_some() {
+        // Clear model only when switching providers (old model may be invalid)
+        if self.settings.llm_backend.as_deref() != Some(backend) {
             self.settings.selected_model = None;
         }
+        self.settings.llm_backend = Some(backend.to_string());
 
         // Check env var first
         if let Ok(existing) = std::env::var(env_var) {
@@ -1181,10 +1198,11 @@ impl SetupWizard {
         &mut self,
         def: &crate::llm::ProviderDefinition,
     ) -> Result<(), SetupError> {
-        self.settings.llm_backend = Some(def.id.clone());
-        if self.settings.selected_model.is_some() {
+        // Clear model only when switching providers (old model may be invalid)
+        if self.settings.llm_backend.as_deref() != Some(&def.id) {
             self.settings.selected_model = None;
         }
+        self.settings.llm_backend = Some(def.id.clone());
 
         let default_url = self
             .settings
@@ -1219,10 +1237,11 @@ impl SetupWizard {
         secret_name: &str,
         display_name: &str,
     ) -> Result<(), SetupError> {
-        self.settings.llm_backend = Some(backend_id.to_string());
-        if self.settings.selected_model.is_some() {
+        // Clear model only when switching providers (old model may be invalid)
+        if self.settings.llm_backend.as_deref() != Some(backend_id) {
             self.settings.selected_model = None;
         }
+        self.settings.llm_backend = Some(backend_id.to_string());
 
         let existing_url = self
             .settings
@@ -1476,6 +1495,7 @@ impl SetupWizard {
                 smart_routing_cascade: true,
             },
             provider: None,
+            request_timeout_secs: 120,
         };
 
         match create_llm_provider(&config, session) {
@@ -2324,6 +2344,12 @@ impl SetupWizard {
             env_vars.push(("NEARAI_API_KEY".to_string(), api_key));
         }
 
+        // Secrets master key (env var mode): write to .env so it's available
+        // on next startup before the DB is connected.
+        if let Some(ref key_hex) = self.settings.secrets_master_key_hex {
+            env_vars.push(("SECRETS_MASTER_KEY".to_string(), key_hex.clone()));
+        }
+
         // Always write ONBOARD_COMPLETED so that check_onboard_needed()
         // (which runs before the DB is connected) knows to skip re-onboarding.
         if self.settings.onboard_completed {
@@ -3499,6 +3525,48 @@ mod tests {
         }
     }
 
+    /// Regression test for #600: re-running provider setup for the same backend
+    /// must NOT clear selected_model. Only switching to a different backend should.
+    #[test]
+    fn test_same_provider_preserves_selected_model() {
+        let mut wizard = SetupWizard::new();
+        wizard.settings.llm_backend = Some("ollama".to_string());
+        wizard.settings.selected_model = Some("llama3".to_string());
+
+        // Simulate re-entering the same provider -- model should survive
+        // (This is the check that each setup_* function now performs)
+        if wizard.settings.llm_backend.as_deref() != Some("ollama") {
+            wizard.settings.selected_model = None;
+        }
+        wizard.settings.llm_backend = Some("ollama".to_string());
+
+        assert_eq!(
+            wizard.settings.selected_model.as_deref(),
+            Some("llama3"),
+            "model should be preserved when re-selecting the same provider"
+        );
+    }
+
+    /// Regression test for #600: switching to a different provider must clear
+    /// selected_model since the old model may not be valid for the new backend.
+    #[test]
+    fn test_different_provider_clears_selected_model() {
+        let mut wizard = SetupWizard::new();
+        wizard.settings.llm_backend = Some("ollama".to_string());
+        wizard.settings.selected_model = Some("llama3".to_string());
+
+        // Simulate switching to a different provider -- model should be cleared
+        if wizard.settings.llm_backend.as_deref() != Some("openai") {
+            wizard.settings.selected_model = None;
+        }
+        wizard.settings.llm_backend = Some("openai".to_string());
+
+        assert!(
+            wizard.settings.selected_model.is_none(),
+            "model should be cleared when switching providers"
+        );
+    }
+
     #[tokio::test]
     async fn test_run_provider_setup_no_setup_hint() {
         // A provider with setup: None should not error. It should set the
@@ -3536,4 +3604,30 @@ mod tests {
             "backend should be set even without setup hint"
         );
     }
+
+    /// Regression test for #666: env-var security option must initialize
+    /// secrets_crypto so subsequent steps can encrypt API keys.
+    #[test]
+    fn test_env_var_security_initializes_crypto() {
+        use crate::secrets::SecretsCrypto;
+        use secrecy::SecretString;
+
+        // Simulate what option 1 in step_security() does after the fix:
+        let key_hex = crate::secrets::keychain::generate_master_key_hex();
+
+        // The fix: create SecretsCrypto from the generated key.
+        // Before the fix, this was skipped, leaving secrets_crypto = None.
+        let crypto = SecretsCrypto::new(SecretString::from(key_hex.clone()));
+        assert!(
+            crypto.is_ok(),
+            "generated key hex must produce valid SecretsCrypto"
+        );
+
+        // Verify the key is stored for bootstrap env persistence.
+        let settings = Settings {
+            secrets_master_key_hex: Some(key_hex),
+            ..Settings::default()
+        };
+        assert!(settings.secrets_master_key_hex.is_some());
+    }
 }

src/testing.rs

@@ -1009,6 +1009,7 @@ mod tests {
             enabled: true,
             trigger: Trigger::Cron {
                 schedule: "0 * * * *".to_string(),
+                timezone: None,
             },
             action: RoutineAction::Lightweight {
                 prompt: "Check status".to_string(),

src/timezone.rs

@@ -0,0 +1,110 @@
+//! Timezone resolution and utilities.
+
+use chrono::{DateTime, NaiveDate, Utc};
+use chrono_tz::Tz;
+
+/// Resolve the effective timezone from a priority chain.
+///
+/// Priority: client_tz > user_setting > config_default > UTC
+pub fn resolve_timezone(
+    client_tz: Option<&str>,
+    user_setting: Option<&str>,
+    config_default: &str,
+) -> Tz {
+    // Try each in priority order, skipping invalid values
+    for candidate in [client_tz, user_setting, Some(config_default)] {
+        if let Some(tz) = candidate.and_then(parse_timezone) {
+            return tz;
+        }
+    }
+    Tz::UTC
+}
+
+/// Parse a timezone string (IANA name) into a `Tz`.
+pub fn parse_timezone(s: &str) -> Option<Tz> {
+    s.parse::<Tz>().ok()
+}
+
+/// Get today's date in the given timezone.
+pub fn today_in_tz(tz: Tz) -> NaiveDate {
+    Utc::now().with_timezone(&tz).date_naive()
+}
+
+/// Get the current time in the given timezone.
+pub fn now_in_tz(tz: Tz) -> DateTime<Tz> {
+    Utc::now().with_timezone(&tz)
+}
+
+/// Detect the system's timezone, falling back to UTC.
+pub fn detect_system_timezone() -> Tz {
+    iana_time_zone::get_timezone()
+        .ok()
+        .and_then(|s| parse_timezone(&s))
+        .unwrap_or(Tz::UTC)
+}
+
+#[cfg(test)]
+mod tests {
+    use chrono::Datelike;
+
+    use super::*;
+
+    #[test]
+    fn test_resolve_client_wins() {
+        let tz = resolve_timezone(Some("America/New_York"), Some("Europe/London"), "UTC");
+        assert_eq!(tz, chrono_tz::America::New_York);
+    }
+
+    #[test]
+    fn test_resolve_user_setting_fallback() {
+        let tz = resolve_timezone(None, Some("Europe/London"), "UTC");
+        assert_eq!(tz, chrono_tz::Europe::London);
+    }
+
+    #[test]
+    fn test_resolve_config_fallback() {
+        let tz = resolve_timezone(None, None, "Asia/Tokyo");
+        assert_eq!(tz, chrono_tz::Asia::Tokyo);
+    }
+
+    #[test]
+    fn test_resolve_all_none_utc() {
+        let tz = resolve_timezone(None, None, "UTC");
+        assert_eq!(tz, Tz::UTC);
+    }
+
+    #[test]
+    fn test_resolve_invalid_client_skipped() {
+        let tz = resolve_timezone(Some("Fake/Zone"), Some("Europe/London"), "UTC");
+        assert_eq!(tz, chrono_tz::Europe::London);
+    }
+
+    #[test]
+    fn test_parse_valid() {
+        assert_eq!(
+            parse_timezone("America/Chicago"),
+            Some(chrono_tz::America::Chicago)
+        );
+    }
+
+    #[test]
+    fn test_parse_invalid() {
+        assert_eq!(parse_timezone("Fake/Zone"), None);
+    }
+
+    #[test]
+    fn test_detect_system_tz() {
+        // Should always return a valid Tz (at minimum UTC)
+        let tz = detect_system_timezone();
+        let _ = now_in_tz(tz); // Should not panic
+    }
+
+    #[test]
+    fn test_today_in_tz_returns_valid_date() {
+        let date = today_in_tz(Tz::UTC);
+        // Verify it returns a valid date (year, month, day are all positive)
+        assert!(date.year() > 0);
+        assert!((1..=12).contains(&date.month()));
+        assert!((1..=31).contains(&date.day()));
+    }
+}

src/tools/builder/core.rs

@@ -43,7 +43,6 @@ use crate::error::ToolError as AgentToolError;
 use crate::llm::{
     ChatMessage, LlmProvider, Reasoning, ReasoningContext, RespondResult, ToolDefinition,
 };
-use crate::safety::SafetyLayer;
 use crate::tools::ToolRegistry;
 use crate::tools::tool::{ApprovalRequirement, Tool, ToolError, ToolOutput};
 
@@ -251,29 +250,18 @@ pub trait SoftwareBuilder: Send + Sync {
 pub struct LlmSoftwareBuilder {
     config: BuilderConfig,
     llm: Arc<dyn LlmProvider>,
-    safety: Arc<SafetyLayer>,
     tools: Arc<ToolRegistry>,
 }
 
 impl LlmSoftwareBuilder {
     /// Create a new LLM-based software builder.
-    pub fn new(
-        config: BuilderConfig,
-        llm: Arc<dyn LlmProvider>,
-        safety: Arc<SafetyLayer>,
-        tools: Arc<ToolRegistry>,
-    ) -> Self {
+    pub fn new(config: BuilderConfig, llm: Arc<dyn LlmProvider>, tools: Arc<ToolRegistry>) -> Self {
         // Ensure build directory exists
         if let Err(e) = std::fs::create_dir_all(&config.build_dir) {
             tracing::warn!("Failed to create build directory: {}", e);
         }
 
-        Self {
-            config,
-            llm,
-            safety,
-            tools,
-        }
+        Self { config, llm, tools }
     }
 
     /// Get the build tools available for the build loop.
@@ -521,7 +509,7 @@ Create alongside the .wasm file to grant capabilities:
         let mut iteration = 0;
 
         // Create reasoning engine
-        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let reasoning = Reasoning::new(self.llm.clone());
 
         // Build initial context
         let tool_defs = self.get_build_tools().await;
@@ -822,7 +810,7 @@ Create alongside the .wasm file to grant capabilities:
 impl SoftwareBuilder for LlmSoftwareBuilder {
     async fn analyze(&self, description: &str) -> Result<BuildRequirement, AgentToolError> {
         // Use LLM to parse the description
-        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let reasoning = Reasoning::new(self.llm.clone());
 
         let prompt = format!(
             r#"Analyze this software requirement and extract structured information.

src/tools/builtin/memory.rs

@@ -172,7 +172,7 @@ impl Tool for MemoryWriteTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -239,11 +239,12 @@ impl Tool for MemoryWriteTool {
                 paths::MEMORY.to_string()
             }
             "daily_log" => {
+                let tz = crate::timezone::parse_timezone(&ctx.user_timezone)
+                    .unwrap_or(chrono_tz::Tz::UTC);
                 self.workspace
-                    .append_daily_log(content)
+                    .append_daily_log_tz(content, tz)
                     .await
-                    .map_err(|e| ToolError::ExecutionFailed(format!("Write failed: {}", e)))?;
-                format!("daily/{}.md", chrono::Utc::now().format("%Y-%m-%d"))
+                    .map_err(|e| ToolError::ExecutionFailed(format!("Write failed: {}", e)))?
             }
             "heartbeat" => {
                 if append {

src/tools/builtin/message.rs

@@ -105,42 +105,47 @@ impl Tool for MessageTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
         let content = require_str(&params, "content")?;
 
-        // Get channel: use param or fall back to default
-        let channel = if let Some(c) = params.get("channel").and_then(|v| v.as_str()) {
-            c.to_string()
-        } else {
-            self.default_channel
+        // Get channel: use param → conversation default → job metadata → None (broadcast all)
+        let channel: Option<String> =
+            if let Some(c) = params.get("channel").and_then(|v| v.as_str()) {
+                Some(c.to_string())
+            } else if let Some(c) = self
+                .default_channel
                 .read()
                 .unwrap_or_else(|e| e.into_inner())
                 .clone()
-                .ok_or_else(|| {
-                    ToolError::ExecutionFailed(
-                        "No channel specified and no active conversation. Provide channel parameter."
-                            .to_string(),
-                    )
-                })?
-        };
+            {
+                Some(c)
+            } else {
+                ctx.metadata
+                    .get("notify_channel")
+                    .and_then(|v| v.as_str())
+                    .map(|c| c.to_string())
+            };
 
-        // Get target: use param or fall back to default
+        // Get target: use param → conversation default → job metadata
         let target = if let Some(t) = params.get("target").and_then(|v| v.as_str()) {
             t.to_string()
+        } else if let Some(t) = self
+            .default_target
+            .read()
+            .unwrap_or_else(|e| e.into_inner())
+            .clone()
+        {
+            t
+        } else if let Some(t) = ctx.metadata.get("notify_user").and_then(|v| v.as_str()) {
+            t.to_string()
         } else {
-            self.default_target
-                .read()
-                .unwrap_or_else(|e| e.into_inner())
-                .clone()
-                .ok_or_else(|| {
-                    ToolError::ExecutionFailed(
-                        "No target specified and no active conversation. Provide target parameter."
-                            .to_string(),
-                    )
-                })?
+            return Err(ToolError::ExecutionFailed(
+                "No target specified and no active conversation. Provide target parameter."
+                    .to_string(),
+            ));
         };
 
         let attachments: Vec<String> = match params.get("attachments") {
@@ -181,36 +186,79 @@ impl Tool for MessageTool {
             response = response.with_attachments(attachments);
         }
 
-        match self
-            .channel_manager
-            .broadcast(&channel, &target, response)
-            .await
-        {
-            Ok(()) => {
-                tracing::info!(
-                    message_sent = true,
-                    channel = %channel,
-                    target = %target,
-                    attachments = attachment_count,
-                    "Message sent via message tool"
-                );
-                let msg = format!("Sent message to {}:{}", channel, target);
-                Ok(ToolOutput::text(msg, start.elapsed()))
+        if let Some(ref channel) = channel {
+            // Send to a specific channel
+            match self
+                .channel_manager
+                .broadcast(channel, &target, response)
+                .await
+            {
+                Ok(()) => {
+                    tracing::info!(
+                        message_sent = true,
+                        channel = %channel,
+                        target = %target,
+                        attachments = attachment_count,
+                        "Message sent via message tool"
+                    );
+                    let msg = format!("Sent message to {}:{}", channel, target);
+                    Ok(ToolOutput::text(msg, start.elapsed()))
+                }
+                Err(e) => {
+                    let available = self.channel_manager.channel_names().await.join(", ");
+                    let err_msg = if available.is_empty() {
+                        format!(
+                            "Failed to send to {}:{}: {}. No channels connected.",
+                            channel, target, e
+                        )
+                    } else {
+                        format!(
+                            "Failed to send to {}:{}. Available channels: {}. Error: {}",
+                            channel, target, available, e
+                        )
+                    };
+                    Err(ToolError::ExecutionFailed(err_msg))
+                }
             }
-            Err(e) => {
-                let available = self.channel_manager.channel_names().await.join(", ");
-                let err_msg = if available.is_empty() {
-                    format!(
-                        "Failed to send to {}:{}: {}. No channels connected.",
-                        channel, target, e
-                    )
+        } else {
+            // No channel specified — broadcast to all channels (routine with notify.channel = None)
+            let results = self.channel_manager.broadcast_all(&target, response).await;
+            let mut succeeded = Vec::new();
+            let mut failed: Vec<&str> = Vec::new();
+            for (ch, result) in &results {
+                match result {
+                    Ok(()) => succeeded.push(ch.as_str()),
+                    Err(e) => {
+                        tracing::warn!(
+                            channel = %ch,
+                            target = %target,
+                            "broadcast_all: channel failed: {}", e
+                        );
+                        failed.push(ch.as_str());
+                    }
+                }
+            }
+            if succeeded.is_empty() {
+                let err_msg = if failed.is_empty() {
+                    "No channels connected.".to_string()
                 } else {
-                    format!(
-                        "Failed to send to {}:{}. Available channels: {}. Error: {}",
-                        channel, target, available, e
-                    )
+                    format!("All channels failed: {}", failed.join(", "))
                 };
                 Err(ToolError::ExecutionFailed(err_msg))
+            } else {
+                tracing::info!(
+                    message_sent = true,
+                    channels = ?succeeded,
+                    target = %target,
+                    attachments = attachment_count,
+                    "Message broadcast via message tool"
+                );
+                let msg = format!(
+                    "Broadcast message to {} (target: {})",
+                    succeeded.join(", "),
+                    target
+                );
+                Ok(ToolOutput::text(msg, start.elapsed()))
             }
         }
     }
@@ -576,4 +624,90 @@ mod tests {
             ApprovalRequirement::Never,
         );
     }
+
+    #[tokio::test]
+    async fn message_tool_falls_back_to_job_metadata() {
+        // Regression: when no conversation context is set (e.g. routine full-job),
+        // the message tool should fall back to notify_channel/notify_user from
+        // JobContext metadata instead of returning "No target specified".
+        let tool = MessageTool::new(Arc::new(ChannelManager::new()));
+
+        let mut ctx = crate::context::JobContext::new("routine-job", "price alert");
+        ctx.metadata = serde_json::json!({
+            "notify_channel": "telegram",
+            "notify_user": "123456789",
+        });
+
+        // No set_context called — simulates a routine full-job worker
+        let result = tool
+            .execute(serde_json::json!({"content": "NEAR price is $5"}), &ctx)
+            .await;
+
+        // Should fail at channel broadcast (no real channel), NOT at
+        // "No target specified and no active conversation"
+        assert!(result.is_err());
+        let err = result.unwrap_err().to_string();
+        assert!(
+            !err.contains("No target specified"),
+            "Should not get 'No target specified' when metadata has notify_user, got: {}",
+            err
+        );
+        assert!(
+            !err.contains("No channel specified"),
+            "Should not get 'No channel specified' when metadata has notify_channel, got: {}",
+            err
+        );
+    }
+
+    #[tokio::test]
+    async fn message_tool_no_metadata_still_errors() {
+        // When neither conversation context nor metadata is set, should still
+        // return a clear error (target resolution fails).
+        let tool = MessageTool::new(Arc::new(ChannelManager::new()));
+        let ctx = crate::context::JobContext::new("orphan-job", "no notify config");
+
+        let result = tool
+            .execute(serde_json::json!({"content": "hello"}), &ctx)
+            .await;
+
+        assert!(result.is_err());
+        let err = result.unwrap_err().to_string();
+        assert!(
+            err.contains("No target specified"),
+            "Expected 'No target specified' error, got: {}",
+            err
+        );
+    }
+
+    #[tokio::test]
+    async fn message_tool_broadcasts_all_when_no_channel() {
+        // Regression: when notify.channel is None but notify_user is set,
+        // the message tool should attempt broadcast_all instead of erroring
+        // with "No channel specified".
+        let tool = MessageTool::new(Arc::new(ChannelManager::new()));
+
+        let mut ctx = crate::context::JobContext::new("routine-job", "price alert");
+        ctx.metadata = serde_json::json!({
+            "notify_user": "123456789",
+        });
+
+        let result = tool
+            .execute(serde_json::json!({"content": "NEAR price is $5"}), &ctx)
+            .await;
+
+        // Should fail because no channels are registered (empty ChannelManager),
+        // NOT because "No channel specified".
+        assert!(result.is_err());
+        let err = result.unwrap_err().to_string();
+        assert!(
+            !err.contains("No channel specified"),
+            "Should not get 'No channel specified' when broadcasting, got: {}",
+            err
+        );
+        assert!(
+            err.contains("No channels connected") || err.contains("All channels failed"),
+            "Expected channel delivery error, got: {}",
+            err
+        );
+    }
 }

src/tools/builtin/routine.rs

@@ -107,6 +107,10 @@ impl Tool for RoutineCreateTool {
                 "notify_user": {
                     "type": "string",
                     "description": "User/target to notify (e.g. username, chat ID). Defaults to 'default'."
+                },
+                "timezone": {
+                    "type": "string",
+                    "description": "IANA timezone for cron schedule evaluation (e.g. 'America/New_York'). Defaults to UTC."
                 }
             },
             "required": ["name", "trigger_type", "prompt"]
@@ -143,12 +147,26 @@ impl Tool for RoutineCreateTool {
                                 "cron trigger requires 'schedule'".to_string(),
                             )
                         })?;
+                let timezone = params
+                    .get("timezone")
+                    .and_then(|v| v.as_str())
+                    .map(|tz| {
+                        crate::timezone::parse_timezone(tz)
+                            .map(|_| tz.to_string())
+                            .ok_or_else(|| {
+                                ToolError::InvalidParameters(format!(
+                                    "invalid IANA timezone: '{tz}'"
+                                ))
+                            })
+                    })
+                    .transpose()?;
                 // Validate cron expression
-                next_cron_fire(schedule).map_err(|e| {
+                next_cron_fire(schedule, timezone.as_deref()).map_err(|e| {
                     ToolError::InvalidParameters(format!("invalid cron schedule: {e}"))
                 })?;
                 Trigger::Cron {
                     schedule: schedule.to_string(),
+                    timezone,
                 }
             }
             "event" => {
@@ -228,8 +246,12 @@ impl Tool for RoutineCreateTool {
             .unwrap_or(300);
 
         // Compute next fire time for cron
-        let next_fire = if let Trigger::Cron { ref schedule } = trigger {
-            next_cron_fire(schedule).unwrap_or(None)
+        let next_fire = if let Trigger::Cron {
+            ref schedule,
+            ref timezone,
+        } = trigger
+        {
+            next_cron_fire(schedule, timezone.as_deref()).unwrap_or(None)
         } else {
             None
         };
@@ -412,6 +434,10 @@ impl Tool for RoutineUpdateTool {
                     "type": "string",
                     "description": "New cron schedule (for cron triggers)"
                 },
+                "timezone": {
+                    "type": "string",
+                    "description": "IANA timezone for cron schedule (e.g. 'America/New_York'). Only valid for cron triggers."
+                },
                 "description": {
                     "type": "string",
                     "description": "New description"
@@ -453,15 +479,47 @@ impl Tool for RoutineUpdateTool {
             }
         }
 
-        if let Some(schedule) = params.get("schedule").and_then(|v| v.as_str()) {
-            // Validate
-            next_cron_fire(schedule)
-                .map_err(|e| ToolError::InvalidParameters(format!("invalid cron schedule: {e}")))?;
+        // Validate timezone param if provided
+        let new_timezone = params
+            .get("timezone")
+            .and_then(|v| v.as_str())
+            .map(|tz| {
+                crate::timezone::parse_timezone(tz)
+                    .map(|_| tz.to_string())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters(format!("invalid IANA timezone: '{tz}'"))
+                    })
+            })
+            .transpose()?;
 
-            routine.trigger = Trigger::Cron {
-                schedule: schedule.to_string(),
+        let new_schedule = params.get("schedule").and_then(|v| v.as_str());
+
+        if new_schedule.is_some() || new_timezone.is_some() {
+            // Extract existing cron fields (cloned to avoid borrow conflict)
+            let existing_cron = match &routine.trigger {
+                Trigger::Cron { schedule, timezone } => Some((schedule.clone(), timezone.clone())),
+                _ => None,
             };
-            routine.next_fire_at = next_cron_fire(schedule).unwrap_or(None);
+
+            if let Some((old_schedule, old_tz)) = existing_cron {
+                let effective_schedule = new_schedule.unwrap_or(&old_schedule);
+                let effective_tz = new_timezone.or(old_tz);
+                // Validate
+                next_cron_fire(effective_schedule, effective_tz.as_deref()).map_err(|e| {
+                    ToolError::InvalidParameters(format!("invalid cron schedule: {e}"))
+                })?;
+
+                routine.trigger = Trigger::Cron {
+                    schedule: effective_schedule.to_string(),
+                    timezone: effective_tz.clone(),
+                };
+                routine.next_fire_at =
+                    next_cron_fire(effective_schedule, effective_tz.as_deref()).unwrap_or(None);
+            } else {
+                return Err(ToolError::InvalidParameters(
+                    "Cannot update schedule or timezone on a non-cron routine.".to_string(),
+                ));
+            }
         }
 
         self.store

src/tools/builtin/time.rs

@@ -48,7 +48,7 @@ impl Tool for TimeTool {
     async fn execute(
         &self,
         params: serde_json::Value,
-        _ctx: &JobContext,
+        ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
@@ -57,10 +57,15 @@ impl Tool for TimeTool {
         let result = match operation {
             "now" => {
                 let now = Utc::now();
+                let tz =
+                    crate::timezone::parse_timezone(&ctx.user_timezone).unwrap_or(chrono_tz::UTC);
+                let local = now.with_timezone(&tz);
                 serde_json::json!({
                     "iso": now.to_rfc3339(),
                     "unix": now.timestamp(),
-                    "unix_millis": now.timestamp_millis()
+                    "unix_millis": now.timestamp_millis(),
+                    "local_iso": local.to_rfc3339(),
+                    "timezone": tz.name()
                 })
             }
             "parse" => {
@@ -112,3 +117,42 @@ impl Tool for TimeTool {
         false // Internal tool, no external data
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn test_now_includes_local_time_when_timezone_set() {
+        let tool = TimeTool;
+        let mut ctx = JobContext::with_user("test", "chat", "test");
+        ctx.user_timezone = "America/New_York".to_string();
+
+        let output = tool
+            .execute(serde_json::json!({"operation": "now"}), &ctx)
+            .await
+            .expect("execute");
+        assert!(
+            output.result.get("local_iso").is_some(),
+            "should have local_iso"
+        );
+        assert_eq!(
+            output.result["timezone"].as_str(),
+            Some("America/New_York"),
+            "should report timezone"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_now_includes_utc_timezone_by_default() {
+        let tool = TimeTool;
+        let ctx = JobContext::with_user("test", "chat", "test");
+        // Default user_timezone is "UTC" which is a valid IANA timezone
+        let output = tool
+            .execute(serde_json::json!({"operation": "now"}), &ctx)
+            .await
+            .expect("execute");
+        assert!(output.result.get("iso").is_some(), "should have iso");
+        assert_eq!(output.result["timezone"].as_str(), Some("UTC"));
+    }
+}

src/tools/mcp/client.rs

@@ -3,7 +3,6 @@
 //! Supports both local (unauthenticated) and hosted (OAuth-authenticated) servers.
 //! Uses the Streamable HTTP transport with session management.
 
-use std::collections::HashMap;
 use std::sync::Arc;
 use std::sync::atomic::{AtomicU64, Ordering};
 use std::time::Duration;
@@ -53,9 +52,6 @@ pub struct McpClient {
 
     /// Server configuration (for token secret name lookup).
     server_config: Option<McpServerConfig>,
-
-    /// Custom HTTP headers injected into every request.
-    custom_headers: HashMap<String, String>,
 }
 
 impl McpClient {
@@ -79,7 +75,6 @@ impl McpClient {
             secrets: None,
             user_id: "default".to_string(),
             server_config: None,
-            custom_headers: HashMap::new(),
         }
     }
 
@@ -100,28 +95,6 @@ impl McpClient {
             secrets: None,
             user_id: "default".to_string(),
             server_config: None,
-            custom_headers: HashMap::new(),
-        }
-    }
-
-    /// Create a new simple MCP client from a server configuration (no authentication).
-    ///
-    /// Use this when you have an `McpServerConfig` with custom headers but no OAuth.
-    pub fn new_with_config(config: McpServerConfig) -> Self {
-        Self {
-            server_name: config.name.clone(),
-            server_url: config.url.clone(),
-            http_client: reqwest::Client::builder()
-                .timeout(Duration::from_secs(30))
-                .build()
-                .expect("Failed to create HTTP client"),
-            next_id: AtomicU64::new(1),
-            tools_cache: RwLock::new(None),
-            session_manager: None,
-            secrets: None,
-            user_id: "default".to_string(),
-            custom_headers: config.headers.clone(),
-            server_config: Some(config),
         }
     }
 
@@ -146,7 +119,6 @@ impl McpClient {
             session_manager: Some(session_manager),
             secrets: Some(secrets),
             user_id: user_id.into(),
-            custom_headers: config.headers.clone(),
             server_config: Some(config),
         }
     }
@@ -206,12 +178,7 @@ impl McpClient {
                 .header("Content-Type", "application/json")
                 .json(&request);
 
-            // Add custom headers from config
-            for (key, value) in &self.custom_headers {
-                req_builder = req_builder.header(key, value);
-            }
-
-            // Add Authorization header if we have a token (overrides custom Authorization)
+            // Add Authorization header if we have a token
             if let Some(token) = self.get_access_token().await? {
                 req_builder = req_builder.header("Authorization", format!("Bearer {}", token));
             }
@@ -294,9 +261,9 @@ impl McpClient {
         if !response.status().is_success() {
             let status = response.status();
             let body = response.text().await.unwrap_or_default();
+            let preview = sanitize_error_body(&body);
             return Err(ToolError::ExternalService(format!(
-                "MCP server returned status: {} - {}",
-                status, body
+                "MCP server returned status: {status} - {preview}",
             )));
         }
 
@@ -507,7 +474,6 @@ impl Clone for McpClient {
             secrets: self.secrets.clone(),
             user_id: self.user_id.clone(),
             server_config: self.server_config.clone(),
-            custom_headers: self.custom_headers.clone(),
         }
     }
 }
@@ -582,6 +548,58 @@ impl Tool for McpToolWrapper {
     }
 }
 
+/// Sanitize an HTTP error response body for safe display.
+///
+/// Detects full HTML error pages (containing `<html` or `<!DOCTYPE`) and
+/// strips all tags, collapsing whitespace.  Non-HTML bodies are left
+/// intact.  In both cases the result is truncated to 200 *characters*
+/// (char-boundary safe) so that large payloads don't bloat error messages.
+///
+/// See #263 — raw HTML error pages were propagating through the error
+/// chain into the web UI, causing a white screen.
+fn sanitize_error_body(body: &str) -> String {
+    const MAX_CHARS: usize = 200;
+
+    // Only strip tags when the body looks like a full HTML document.
+    // Plain text that happens to contain `<` / `>` (e.g. log lines,
+    // comparison expressions) is left untouched.
+    let lower = body.to_ascii_lowercase();
+    let is_html_document = lower.contains("<html") || lower.contains("<!doctype");
+
+    let text = if is_html_document {
+        let stripped = body
+            .chars()
+            .fold((String::new(), false), |(mut out, in_tag), c| {
+                if c == '<' {
+                    (out, true)
+                } else if c == '>' {
+                    (out, false)
+                } else if !in_tag {
+                    out.push(c);
+                    (out, false)
+                } else {
+                    (out, true)
+                }
+            })
+            .0;
+        stripped.split_whitespace().collect::<Vec<_>>().join(" ")
+    } else {
+        body.to_string()
+    };
+
+    // Truncate at a char boundary (safe for multi-byte UTF-8).
+    if text.chars().count() > MAX_CHARS {
+        let byte_offset = text
+            .char_indices()
+            .nth(MAX_CHARS)
+            .map(|(i, _)| i)
+            .unwrap_or(text.len());
+        format!("{}... ({} bytes total)", &text[..byte_offset], body.len())
+    } else {
+        text
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -726,26 +744,6 @@ mod tests {
         assert_eq!(id3, 3);
     }
 
-    #[test]
-    fn test_custom_headers_from_config() {
-        use std::collections::HashMap;
-        let mut headers = HashMap::new();
-        headers.insert("X-API-Key".to_string(), "secret".to_string());
-        headers.insert("X-Custom".to_string(), "value".to_string());
-
-        let config = McpServerConfig::new("test", "http://localhost:8080").with_headers(headers);
-
-        let client = McpClient::new_with_config(config);
-        assert_eq!(client.custom_headers.len(), 2);
-        assert_eq!(client.custom_headers.get("X-API-Key").unwrap(), "secret");
-    }
-
-    #[test]
-    fn test_new_has_no_custom_headers() {
-        let client = McpClient::new("http://localhost:8080");
-        assert!(client.custom_headers.is_empty());
-    }
-
     #[test]
     fn test_mcp_tool_requires_approval_destructive() {
         use crate::tools::mcp::protocol::{McpTool, McpToolAnnotations};
@@ -794,4 +792,73 @@ mod tests {
         };
         assert!(!tool.requires_approval());
     }
+
+    // Regression tests for #263: HTML error bodies must not propagate raw
+    // markup through the error chain into the web UI.
+
+    #[test]
+    fn test_sanitize_error_body_strips_html_tags() {
+        let html =
+            r#"<!DOCTYPE html><html><body><h1>422 Error</h1><p>Invalid token</p></body></html>"#;
+        let result = sanitize_error_body(html);
+        assert!(!result.contains('<'), "HTML tags must be stripped");
+        assert!(!result.contains('>'), "HTML tags must be stripped");
+        assert!(result.contains("422 Error"));
+        assert!(result.contains("Invalid token"));
+    }
+
+    #[test]
+    fn test_sanitize_error_body_truncates_large_html_page() {
+        let html = format!(
+            "<html><body><p>{}</p></body></html>",
+            "error detail ".repeat(50)
+        );
+        let result = sanitize_error_body(&html);
+        assert!(result.contains("..."));
+        assert!(result.contains("bytes total)"));
+        assert!(!result.contains('<'));
+    }
+
+    #[test]
+    fn test_sanitize_error_body_passes_short_plain_text() {
+        assert_eq!(sanitize_error_body("Not Found"), "Not Found");
+    }
+
+    #[test]
+    fn test_sanitize_error_body_truncates_long_plain_text() {
+        let long = "x".repeat(300);
+        let result = sanitize_error_body(&long);
+        assert!(result.contains("..."));
+        assert!(result.contains("300 bytes total)"));
+    }
+
+    #[test]
+    fn test_sanitize_error_body_multibyte_no_panic() {
+        // 300 CJK characters = 900 bytes; truncation must land on a
+        // char boundary, not in the middle of a multi-byte sequence.
+        let cjk = "错误".repeat(150);
+        let result = sanitize_error_body(&cjk);
+        assert!(result.contains("..."));
+        // Must be valid UTF-8 (would have panicked otherwise).
+        assert!(result.is_char_boundary(result.len()));
+    }
+
+    #[test]
+    fn test_sanitize_error_body_strips_uppercase_html() {
+        let html = "<HTML><BODY><H1>500 Internal Server Error</H1></BODY></HTML>";
+        let result = sanitize_error_body(html);
+        assert!(
+            !result.contains('<'),
+            "uppercase HTML tags must be stripped"
+        );
+        assert!(result.contains("500 Internal Server Error"));
+    }
+
+    #[test]
+    fn test_sanitize_error_body_preserves_angle_brackets_in_non_html() {
+        // Text with < and > that is NOT an HTML document should be
+        // left untouched (e.g. log lines, comparison expressions).
+        let text = "value < 10 and value > 0";
+        assert_eq!(sanitize_error_body(text), text);
+    }
 }

src/tools/mcp/config.rs

@@ -32,13 +32,6 @@ pub struct McpServerConfig {
     /// Optional description for the server.
     #[serde(skip_serializing_if = "Option::is_none")]
     pub description: Option<String>,
-
-    /// Custom HTTP headers to send with every request to this server.
-    ///
-    /// Useful for MCP servers that require non-OAuth authentication
-    /// (e.g., API keys via `X-API-Key` header).
-    #[serde(default, skip_serializing_if = "HashMap::is_empty")]
-    pub headers: HashMap<String, String>,
 }
 
 fn default_true() -> bool {
@@ -54,16 +47,9 @@ impl McpServerConfig {
             oauth: None,
             enabled: true,
             description: None,
-            headers: HashMap::new(),
         }
     }
 
-    /// Set custom HTTP headers for this server.
-    pub fn with_headers(mut self, headers: HashMap<String, String>) -> Self {
-        self.headers = headers;
-        self
-    }
-
     /// Set OAuth configuration.
     pub fn with_oauth(mut self, oauth: OAuthConfig) -> Self {
         self.oauth = Some(oauth);
@@ -607,79 +593,4 @@ mod tests {
         let config = McpServerConfig::new("bad", "http://mcp.example.com");
         assert!(!config.requires_auth());
     }
-
-    #[test]
-    fn test_custom_headers_default_empty() {
-        let config = McpServerConfig::new("test", "http://localhost:8080");
-        assert!(config.headers.is_empty());
-    }
-
-    #[test]
-    fn test_custom_headers_with_builder() {
-        let mut headers = HashMap::new();
-        headers.insert("X-API-Key".to_string(), "secret123".to_string());
-        headers.insert("X-Custom".to_string(), "value".to_string());
-
-        let config = McpServerConfig::new("browser-use", "https://mcp.browser-use.com")
-            .with_headers(headers.clone());
-
-        assert_eq!(config.headers.len(), 2);
-        assert_eq!(config.headers.get("X-API-Key").unwrap(), "secret123");
-    }
-
-    #[test]
-    fn test_custom_headers_serde_roundtrip() {
-        let mut headers = HashMap::new();
-        headers.insert("Authorization".to_string(), "Bearer tok_123".to_string());
-
-        let config =
-            McpServerConfig::new("test-serde", "http://localhost:3000").with_headers(headers);
-
-        let json = serde_json::to_string(&config).unwrap();
-        let deserialized: McpServerConfig = serde_json::from_str(&json).unwrap();
-
-        assert_eq!(deserialized.headers.len(), 1);
-        assert_eq!(
-            deserialized.headers.get("Authorization").unwrap(),
-            "Bearer tok_123"
-        );
-    }
-
-    #[test]
-    fn test_custom_headers_absent_in_json_defaults_empty() {
-        let json = serde_json::json!({
-            "name": "legacy",
-            "url": "http://localhost:8080"
-        });
-        let config: McpServerConfig = serde_json::from_value(json).unwrap();
-        assert!(config.headers.is_empty());
-    }
-
-    #[test]
-    fn test_custom_headers_skipped_when_empty_in_serialization() {
-        let config = McpServerConfig::new("minimal", "http://localhost:8080");
-        let json = serde_json::to_value(&config).unwrap();
-        // Empty headers map should not appear in serialized output
-        assert!(json.get("headers").is_none());
-    }
-
-    #[tokio::test]
-    async fn test_custom_headers_persist_to_disk() {
-        let dir = tempdir().unwrap();
-        let path = dir.path().join("mcp-headers-test.json");
-
-        let mut headers = HashMap::new();
-        headers.insert("X-API-Key".to_string(), "key123".to_string());
-
-        let mut config = McpServersFile::default();
-        config.upsert(
-            McpServerConfig::new("headered", "http://localhost:9090").with_headers(headers),
-        );
-
-        save_mcp_servers_to(&config, &path).await.unwrap();
-        let loaded = load_mcp_servers_from(&path).await.unwrap();
-
-        let server = loaded.get("headered").unwrap();
-        assert_eq!(server.headers.get("X-API-Key").unwrap(), "key123");
-    }
 }

src/tools/registry.rs

@@ -10,7 +10,6 @@ use crate::db::Database;
 use crate::extensions::ExtensionManager;
 use crate::llm::{LlmProvider, ToolDefinition};
 use crate::orchestrator::job_manager::ContainerJobManager;
-use crate::safety::SafetyLayer;
 use crate::secrets::SecretsStore;
 use crate::skills::catalog::SkillCatalog;
 use crate::skills::registry::SkillRegistry;
@@ -485,17 +484,15 @@ impl ToolRegistry {
     pub async fn register_builder_tool(
         self: &Arc<Self>,
         llm: Arc<dyn LlmProvider>,
-        safety: Arc<SafetyLayer>,
         config: Option<BuilderConfig>,
     ) {
         // First register dev tools needed by the builder
         self.register_dev_tools();
 
-        // Create the builder (arg order: config, llm, safety, tools)
+        // Create the builder (arg order: config, llm, tools)
         let builder = Arc::new(LlmSoftwareBuilder::new(
             config.unwrap_or_default(),
             llm,
-            safety,
             Arc::clone(self),
         ));
 

src/worker/runtime.rs

@@ -133,7 +133,7 @@ impl WorkerRuntime {
             .await?;
 
         // Create reasoning engine
-        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let reasoning = Reasoning::new(self.llm.clone());
 
         // Build initial context
         let mut reason_ctx = ReasoningContext::new().with_job(&job.description);

src/workspace/chunker.rs

@@ -113,79 +113,6 @@ pub fn chunk_document(content: &str, config: ChunkConfig) -> Vec<String> {
     chunks
 }
 
-/// Split content by paragraphs first, then chunk.
-///
-/// This is better for preserving semantic boundaries.
-#[allow(dead_code)] // Alternative chunking strategy for paragraph-aware indexing
-pub fn chunk_by_paragraphs(content: &str, config: ChunkConfig) -> Vec<String> {
-    if content.is_empty() {
-        return Vec::new();
-    }
-
-    // Split by double newlines (paragraphs)
-    let paragraphs: Vec<&str> = content
-        .split("\n\n")
-        .map(|p| p.trim())
-        .filter(|p| !p.is_empty())
-        .collect();
-
-    if paragraphs.is_empty() {
-        return chunk_document(content, config);
-    }
-
-    let mut chunks = Vec::new();
-    let mut current_chunk = String::new();
-    let mut current_word_count = 0;
-
-    for paragraph in paragraphs {
-        let para_words = paragraph.split_whitespace().count();
-
-        // If this paragraph alone exceeds chunk size, chunk it separately
-        if para_words > config.chunk_size {
-            // Flush current chunk first
-            if !current_chunk.is_empty() {
-                chunks.push(current_chunk.trim().to_string());
-                current_chunk = String::new();
-                current_word_count = 0;
-            }
-            // Chunk the large paragraph
-            let para_chunks = chunk_document(paragraph, config.clone());
-            chunks.extend(para_chunks);
-            continue;
-        }
-
-        // Check if adding this paragraph would exceed chunk size
-        if current_word_count + para_words > config.chunk_size {
-            // Flush current chunk
-            if !current_chunk.is_empty() {
-                chunks.push(current_chunk.trim().to_string());
-            }
-            current_chunk = paragraph.to_string();
-            current_word_count = para_words;
-        } else {
-            // Add paragraph to current chunk
-            if !current_chunk.is_empty() {
-                current_chunk.push_str("\n\n");
-            }
-            current_chunk.push_str(paragraph);
-            current_word_count += para_words;
-        }
-    }
-
-    // Flush remaining content
-    if !current_chunk.is_empty() {
-        // If too small, merge with previous chunk if possible
-        if current_word_count < config.min_chunk_size && !chunks.is_empty() {
-            let last = chunks.pop().unwrap();
-            chunks.push(format!("{}\n\n{}", last, current_chunk.trim()));
-        } else {
-            chunks.push(current_chunk.trim().to_string());
-        }
-    }
-
-    chunks
-}
-
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -253,49 +180,6 @@ mod tests {
         assert_eq!(config.step_size(), 85);
     }
 
-    #[test]
-    fn test_paragraph_chunking() {
-        let config = ChunkConfig::default().with_chunk_size(20);
-
-        let content = "First paragraph with some words.\n\nSecond paragraph with different content.\n\nThird paragraph here.";
-        let chunks = chunk_by_paragraphs(content, config);
-
-        // Should preserve paragraph boundaries
-        assert!(!chunks.is_empty());
-        for chunk in &chunks {
-            // No chunk should start or end with \n\n
-            assert!(!chunk.starts_with("\n"));
-            assert!(!chunk.ends_with("\n"));
-        }
-    }
-
-    #[test]
-    fn test_large_paragraph_handling() {
-        let config = ChunkConfig {
-            chunk_size: 10,
-            overlap_percent: 0.15,
-            min_chunk_size: 3, // Low threshold for test
-        };
-
-        // Create a paragraph with 30 words
-        let large_para = (1..=30)
-            .map(|i| format!("word{}", i))
-            .collect::<Vec<_>>()
-            .join(" ");
-        let content = format!("Short intro.\n\n{}\n\nShort outro.", large_para);
-
-        let chunks = chunk_by_paragraphs(&content, config);
-
-        // Should have multiple chunks due to large paragraph
-        // 30 words + 2 intro + 2 outro = 34 words, chunk_size=10
-        // Expect at least 3 chunks
-        assert!(
-            chunks.len() >= 3,
-            "Expected at least 3 chunks for 34 words with chunk_size=10, got {}",
-            chunks.len()
-        );
-    }
-
     #[test]
     fn test_min_chunk_size_merging() {
         let config = ChunkConfig {

src/workspace/lancedb_store.rs

@@ -0,0 +1,644 @@
+//! LanceDB-backed vector store for workspace memory chunks.
+//!
+//! Provides an alternative to pgvector/libsql for semantic search when the
+//! `lancedb` feature is enabled. Documents and metadata stay in the main
+//! database; this store holds chunk embeddings for vector similarity search.
+//!
+//! Configuration:
+//!   LANCEDB_PATH=~/.ironclaw/lancedb   # Default
+//!   VECTOR_BACKEND=lancedb             # Use LanceDB for vector search
+
+/// Default embedding dimension (text-embedding-3-small).
+/// Override by passing the actual provider dimension to `LanceDbVectorStore::new()`.
+pub const DEFAULT_EMBEDDING_DIM: i32 = 1536;
+
+#[cfg(feature = "lancedb")]
+mod impl_lancedb {
+    use std::sync::Arc;
+
+    use arrow_array::types::Float32Type;
+    use arrow_array::{Array, FixedSizeListArray, RecordBatch, RecordBatchIterator, StringArray};
+    use arrow_schema::{DataType, Field, Schema};
+    use async_trait::async_trait;
+    use futures::StreamExt;
+    use lancedb::query::{ExecutableQuery, QueryBase};
+    use uuid::Uuid;
+
+    use super::DEFAULT_EMBEDDING_DIM;
+    use crate::error::WorkspaceError;
+    use crate::workspace::search::RankedResult;
+    use crate::workspace::vector_store::VectorStore;
+
+    const TABLE_NAME: &str = "memory_chunks";
+
+    /// Escapes a string for safe use in LanceDB predicate expressions.
+    /// Uses SQL-style escaping: single quotes are doubled to prevent injection.
+    fn escape_predicate_value(s: &str) -> String {
+        s.replace('\'', "''")
+    }
+
+    /// LanceDB-backed vector store.
+    ///
+    /// The `update_embedding` method uses delete-then-insert (not atomic).
+    /// LanceDB does not support transactions, so a crash between the two
+    /// operations can lose the embedding for that chunk. This is acceptable
+    /// for personal workspace sizes where data can be reindexed.
+    pub struct LanceDbVectorStore {
+        db: Arc<lancedb::Connection>,
+        table_name: String,
+        embedding_dim: i32,
+        schema: Arc<Schema>,
+        table: tokio::sync::OnceCell<lancedb::Table>,
+    }
+
+    impl LanceDbVectorStore {
+        /// Create a new LanceDB store at the given path.
+        ///
+        /// `embedding_dim` should match `EmbeddingProvider::dimension()`.
+        /// Pass `None` to use the default (1536, text-embedding-3-small).
+        pub async fn new(
+            path: impl AsRef<std::path::Path>,
+            embedding_dim: Option<usize>,
+        ) -> Result<Self, WorkspaceError> {
+            let path_str = path
+                .as_ref()
+                .to_str()
+                .ok_or_else(|| WorkspaceError::SearchFailed {
+                    reason: "Invalid LanceDB path".to_string(),
+                })?;
+
+            let db = lancedb::connect(path_str).execute().await.map_err(|e| {
+                WorkspaceError::SearchFailed {
+                    reason: format!("Failed to connect to LanceDB: {}", e),
+                }
+            })?;
+
+            let dim = embedding_dim.unwrap_or(DEFAULT_EMBEDDING_DIM as usize) as i32;
+            let schema = Arc::new(Self::build_schema(dim));
+
+            let store = Self {
+                db: Arc::new(db),
+                table_name: TABLE_NAME.to_string(),
+                embedding_dim: dim,
+                schema,
+                table: tokio::sync::OnceCell::new(),
+            };
+
+            store.ensure_table().await?;
+            Ok(store)
+        }
+
+        async fn ensure_table(&self) -> Result<(), WorkspaceError> {
+            let tables = self.db.table_names().execute().await.map_err(|e| {
+                WorkspaceError::SearchFailed {
+                    reason: format!("Failed to list tables: {}", e),
+                }
+            })?;
+
+            if tables.iter().any(|t| t == &self.table_name) {
+                return Ok(());
+            }
+
+            self.db
+                .create_empty_table(&self.table_name, self.schema.clone())
+                .execute()
+                .await
+                .map_err(|e| WorkspaceError::SearchFailed {
+                    reason: format!("Failed to create table: {}", e),
+                })?;
+
+            // Index creation is deferred — brute-force search via
+            // bypass_vector_index() works without a pre-built index and is
+            // sufficient for personal workspace sizes.
+            Ok(())
+        }
+
+        /// Get or open the cached table handle.
+        async fn table(&self) -> Result<&lancedb::Table, WorkspaceError> {
+            self.table
+                .get_or_try_init(|| async {
+                    self.db
+                        .open_table(&self.table_name)
+                        .execute()
+                        .await
+                        .map_err(|e| WorkspaceError::SearchFailed {
+                            reason: format!("Failed to open table: {}", e),
+                        })
+                })
+                .await
+        }
+
+        fn build_schema(embedding_dim: i32) -> Schema {
+            Schema::new(vec![
+                Field::new("chunk_id", DataType::Utf8, false),
+                Field::new("document_id", DataType::Utf8, false),
+                Field::new("document_path", DataType::Utf8, false),
+                Field::new("user_id", DataType::Utf8, false),
+                Field::new("agent_id", DataType::Utf8, true),
+                Field::new("content", DataType::Utf8, false),
+                Field::new(
+                    "vector",
+                    DataType::FixedSizeList(
+                        Arc::new(Field::new("item", DataType::Float32, true)),
+                        embedding_dim,
+                    ),
+                    false,
+                ),
+            ])
+        }
+    }
+
+    #[async_trait]
+    impl VectorStore for LanceDbVectorStore {
+        async fn store_embedding(
+            &self,
+            chunk_id: Uuid,
+            document_id: Uuid,
+            document_path: &str,
+            user_id: &str,
+            agent_id: Option<Uuid>,
+            content: &str,
+            embedding: &[f32],
+        ) -> Result<(), WorkspaceError> {
+            if embedding.len() != self.embedding_dim as usize {
+                return Err(WorkspaceError::EmbeddingFailed {
+                    reason: format!(
+                        "Embedding dimension {} does not match expected {}",
+                        embedding.len(),
+                        self.embedding_dim
+                    ),
+                });
+            }
+
+            let table = self.table().await?;
+
+            let chunk_ids = StringArray::from(vec![chunk_id.to_string()]);
+            let document_ids = StringArray::from(vec![document_id.to_string()]);
+            let document_paths = StringArray::from(vec![document_path]);
+            let user_ids = StringArray::from(vec![user_id]);
+            let agent_ids = StringArray::from(vec![agent_id.map(|a| a.to_string())]);
+            let contents = StringArray::from(vec![content]);
+            let vec_values: Vec<Option<f32>> = embedding.iter().map(|&x| Some(x)).collect();
+            let vectors = FixedSizeListArray::from_iter_primitive::<Float32Type, _, _>(
+                vec![Some(vec_values)],
+                self.embedding_dim,
+            );
+
+            let batch = RecordBatch::try_new(
+                self.schema.clone(),
+                vec![
+                    Arc::new(chunk_ids),
+                    Arc::new(document_ids),
+                    Arc::new(document_paths),
+                    Arc::new(user_ids),
+                    Arc::new(agent_ids),
+                    Arc::new(contents),
+                    Arc::new(vectors),
+                ],
+            )
+            .map_err(|e| WorkspaceError::EmbeddingFailed {
+                reason: format!("Failed to create record batch: {}", e),
+            })?;
+
+            let batches =
+                RecordBatchIterator::new(vec![Ok(batch)].into_iter(), self.schema.clone());
+
+            table
+                .add(Box::new(batches) as Box<dyn arrow_array::RecordBatchReader + Send>)
+                .execute()
+                .await
+                .map_err(|e| WorkspaceError::EmbeddingFailed {
+                    reason: format!("Failed to store embedding: {}", e),
+                })?;
+
+            Ok(())
+        }
+
+        async fn update_embedding(
+            &self,
+            chunk_id: Uuid,
+            document_id: Uuid,
+            document_path: &str,
+            user_id: &str,
+            agent_id: Option<Uuid>,
+            content: &str,
+            embedding: &[f32],
+        ) -> Result<(), WorkspaceError> {
+            let table = self.table().await?;
+
+            table
+                .delete(&format!(
+                    "chunk_id = '{}'",
+                    escape_predicate_value(&chunk_id.to_string())
+                ))
+                .await
+                .map_err(|e| WorkspaceError::EmbeddingFailed {
+                    reason: format!("Failed to delete chunk for update: {}", e),
+                })?;
+
+            self.store_embedding(
+                chunk_id,
+                document_id,
+                document_path,
+                user_id,
+                agent_id,
+                content,
+                embedding,
+            )
+            .await
+        }
+
+        async fn delete_embeddings(&self, document_id: Uuid) -> Result<(), WorkspaceError> {
+            let table = self.table().await?;
+
+            table
+                .delete(&format!(
+                    "document_id = '{}'",
+                    escape_predicate_value(&document_id.to_string())
+                ))
+                .await
+                .map_err(|e| WorkspaceError::EmbeddingFailed {
+                    reason: format!("Failed to delete embeddings: {}", e),
+                })?;
+
+            Ok(())
+        }
+
+        async fn vector_search(
+            &self,
+            user_id: &str,
+            agent_id: Option<Uuid>,
+            embedding: &[f32],
+            limit: usize,
+        ) -> Result<Vec<RankedResult>, WorkspaceError> {
+            let table = self.table().await?;
+
+            let filter = if let Some(aid) = agent_id {
+                format!(
+                    "user_id = '{}' AND agent_id = '{}'",
+                    escape_predicate_value(user_id),
+                    escape_predicate_value(&aid.to_string())
+                )
+            } else {
+                format!(
+                    "user_id = '{}' AND agent_id IS NULL",
+                    escape_predicate_value(user_id)
+                )
+            };
+
+            let query = table
+                .query()
+                .nearest_to(embedding)
+                .map_err(|e| WorkspaceError::SearchFailed {
+                    reason: format!("Invalid query vector: {}", e),
+                })?
+                .only_if(&filter)
+                .bypass_vector_index()
+                .limit(limit);
+            let mut stream = ExecutableQuery::execute(&query).await.map_err(|e| {
+                WorkspaceError::SearchFailed {
+                    reason: format!("Vector search failed: {}", e),
+                }
+            })?;
+
+            let mut results = Vec::new();
+            let mut rank: u32 = 1;
+            while let Some(batch_result) = stream.next().await {
+                let batch = batch_result.map_err(|e| WorkspaceError::SearchFailed {
+                    reason: format!("Stream error: {}", e),
+                })?;
+
+                let chunk_id_col = batch.column_by_name("chunk_id").ok_or_else(|| {
+                    WorkspaceError::SearchFailed {
+                        reason: "chunk_id column missing".to_string(),
+                    }
+                })?;
+                let document_id_col = batch.column_by_name("document_id").ok_or_else(|| {
+                    WorkspaceError::SearchFailed {
+                        reason: "document_id column missing".to_string(),
+                    }
+                })?;
+                let document_path_col = batch.column_by_name("document_path").ok_or_else(|| {
+                    WorkspaceError::SearchFailed {
+                        reason: "document_path column missing".to_string(),
+                    }
+                })?;
+                let content_col = batch.column_by_name("content").ok_or_else(|| {
+                    WorkspaceError::SearchFailed {
+                        reason: "content column missing".to_string(),
+                    }
+                })?;
+
+                let chunk_ids = chunk_id_col
+                    .as_any()
+                    .downcast_ref::<StringArray>()
+                    .ok_or_else(|| WorkspaceError::SearchFailed {
+                        reason: "chunk_id wrong type".to_string(),
+                    })?;
+                let document_ids = document_id_col
+                    .as_any()
+                    .downcast_ref::<StringArray>()
+                    .ok_or_else(|| WorkspaceError::SearchFailed {
+                        reason: "document_id wrong type".to_string(),
+                    })?;
+                let document_paths = document_path_col
+                    .as_any()
+                    .downcast_ref::<StringArray>()
+                    .ok_or_else(|| WorkspaceError::SearchFailed {
+                        reason: "document_path wrong type".to_string(),
+                    })?;
+                let contents = content_col
+                    .as_any()
+                    .downcast_ref::<StringArray>()
+                    .ok_or_else(|| WorkspaceError::SearchFailed {
+                        reason: "content wrong type".to_string(),
+                    })?;
+
+                for i in 0..batch.num_rows() {
+                    let raw_chunk_id = chunk_ids.value(i);
+                    let chunk_id =
+                        raw_chunk_id
+                            .parse::<Uuid>()
+                            .map_err(|e| WorkspaceError::SearchFailed {
+                                reason: format!("Invalid chunk_id UUID '{}': {}", raw_chunk_id, e),
+                            })?;
+
+                    let raw_document_id = document_ids.value(i);
+                    let document_id = raw_document_id.parse::<Uuid>().map_err(|e| {
+                        WorkspaceError::SearchFailed {
+                            reason: format!(
+                                "Invalid document_id UUID '{}': {}",
+                                raw_document_id, e
+                            ),
+                        }
+                    })?;
+                    let document_path = document_paths.value(i).to_string();
+                    let content = contents.value(i).to_string();
+
+                    results.push(RankedResult {
+                        chunk_id,
+                        document_id,
+                        document_path,
+                        content,
+                        rank,
+                    });
+                    rank += 1;
+                }
+            }
+
+            Ok(results)
+        }
+    }
+}
+
+#[cfg(feature = "lancedb")]
+pub use impl_lancedb::LanceDbVectorStore;
+
+#[cfg(all(test, feature = "lancedb"))]
+mod tests {
+    use tempfile::TempDir;
+    use uuid::Uuid;
+
+    use super::{DEFAULT_EMBEDDING_DIM, LanceDbVectorStore};
+    use crate::workspace::vector_store::VectorStore;
+
+    fn make_embedding(seed: f32) -> Vec<f32> {
+        (0..DEFAULT_EMBEDDING_DIM as usize)
+            .map(|i| (seed * (i as f32 + 1.0)).sin())
+            .collect()
+    }
+
+    #[tokio::test]
+    async fn test_insert_and_vector_search() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let chunk_id = Uuid::new_v4();
+        let document_id = Uuid::new_v4();
+        let user_id = "user1";
+        let content = "Rust is a systems programming language";
+        let embedding = make_embedding(1.0);
+
+        store
+            .store_embedding(
+                chunk_id,
+                document_id,
+                "test.md",
+                user_id,
+                None,
+                content,
+                &embedding,
+            )
+            .await
+            .unwrap();
+
+        let results = store
+            .vector_search(user_id, None, &embedding, 5)
+            .await
+            .unwrap();
+
+        assert_eq!(results.len(), 1);
+        assert_eq!(results[0].chunk_id, chunk_id);
+        assert_eq!(results[0].document_id, document_id);
+        assert_eq!(results[0].content, content);
+        assert_eq!(results[0].rank, 1);
+    }
+
+    #[tokio::test]
+    async fn test_insert_multiple_and_search_returns_ordered() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let doc_id = Uuid::new_v4();
+        let user_id = "user1";
+
+        for (i, seed) in [1.0, 2.0, 3.0].iter().enumerate() {
+            store
+                .store_embedding(
+                    Uuid::new_v4(),
+                    doc_id,
+                    "test.md",
+                    user_id,
+                    None,
+                    &format!("content {}", i),
+                    &make_embedding(*seed),
+                )
+                .await
+                .unwrap();
+        }
+
+        let query_emb = make_embedding(2.0);
+        let results = store
+            .vector_search(user_id, None, &query_emb, 5)
+            .await
+            .unwrap();
+
+        assert_eq!(results.len(), 3);
+        let contents: Vec<_> = results.iter().map(|r| r.content.as_str()).collect();
+        assert!(contents.contains(&"content 0"));
+        assert!(contents.contains(&"content 1"));
+        assert!(contents.contains(&"content 2"));
+    }
+
+    #[tokio::test]
+    async fn test_delete_chunks() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let doc_id = Uuid::new_v4();
+        let user_id = "user1";
+
+        store
+            .store_embedding(
+                Uuid::new_v4(),
+                doc_id,
+                "test.md",
+                user_id,
+                None,
+                "content",
+                &make_embedding(1.0),
+            )
+            .await
+            .unwrap();
+
+        let results = store
+            .vector_search(user_id, None, &make_embedding(1.0), 5)
+            .await
+            .unwrap();
+        assert_eq!(results.len(), 1);
+
+        store.delete_embeddings(doc_id).await.unwrap();
+
+        let results_after = store
+            .vector_search(user_id, None, &make_embedding(1.0), 5)
+            .await
+            .unwrap();
+        assert!(results_after.is_empty());
+    }
+
+    #[tokio::test]
+    async fn test_update_chunk_embedding() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let chunk_id = Uuid::new_v4();
+        let doc_id = Uuid::new_v4();
+        let user_id = "user1";
+        let content = "original content";
+
+        store
+            .store_embedding(
+                chunk_id,
+                doc_id,
+                "test.md",
+                user_id,
+                None,
+                content,
+                &make_embedding(1.0),
+            )
+            .await
+            .unwrap();
+
+        let new_embedding = make_embedding(5.0);
+        store
+            .update_embedding(
+                chunk_id,
+                doc_id,
+                "test.md",
+                user_id,
+                None,
+                content,
+                &new_embedding,
+            )
+            .await
+            .unwrap();
+
+        let results = store
+            .vector_search(user_id, None, &new_embedding, 5)
+            .await
+            .unwrap();
+        assert_eq!(results.len(), 1);
+        assert_eq!(results[0].chunk_id, chunk_id);
+    }
+
+    #[tokio::test]
+    async fn test_vector_search_filters_by_user_and_agent() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let doc_id = Uuid::new_v4();
+        let embedding = make_embedding(1.0);
+
+        store
+            .store_embedding(
+                Uuid::new_v4(),
+                doc_id,
+                "test.md",
+                "user1",
+                None,
+                "user1 content",
+                &embedding,
+            )
+            .await
+            .unwrap();
+
+        store
+            .store_embedding(
+                Uuid::new_v4(),
+                doc_id,
+                "test.md",
+                "user2",
+                None,
+                "user2 content",
+                &embedding,
+            )
+            .await
+            .unwrap();
+
+        let results_user1 = store
+            .vector_search("user1", None, &embedding, 5)
+            .await
+            .unwrap();
+        assert_eq!(results_user1.len(), 1);
+        assert_eq!(results_user1[0].content, "user1 content");
+
+        let results_user2 = store
+            .vector_search("user2", None, &embedding, 5)
+            .await
+            .unwrap();
+        assert_eq!(results_user2.len(), 1);
+        assert_eq!(results_user2[0].content, "user2 content");
+
+        let results_wrong_user = store
+            .vector_search("user3", None, &embedding, 5)
+            .await
+            .unwrap();
+        assert!(results_wrong_user.is_empty());
+    }
+
+    #[tokio::test]
+    async fn test_insert_rejects_wrong_embedding_dim() {
+        let dir = TempDir::new().unwrap();
+        let store = LanceDbVectorStore::new(dir.path(), None).await.unwrap();
+
+        let wrong_dim: Vec<f32> = vec![1.0; 100];
+
+        let err = store
+            .store_embedding(
+                Uuid::new_v4(),
+                Uuid::new_v4(),
+                "test.md",
+                "user1",
+                None,
+                "content",
+                &wrong_dim,
+            )
+            .await
+            .unwrap_err();
+
+        assert!(matches!(
+            err,
+            crate::error::WorkspaceError::EmbeddingFailed { .. }
+        ));
+    }
+}

src/workspace/mod.rs

@@ -42,20 +42,26 @@
 
 mod chunker;
 mod document;
-mod embeddings;
+pub mod embeddings;
 pub mod hygiene;
+#[cfg(feature = "lancedb")]
+pub mod lancedb_store;
 #[cfg(feature = "postgres")]
 mod repository;
 mod search;
+pub mod vector_store;
 
 pub use chunker::{ChunkConfig, chunk_document};
 pub use document::{MemoryChunk, MemoryDocument, WorkspaceEntry, paths};
 pub use embeddings::{
     EmbeddingProvider, MockEmbeddings, NearAiEmbeddings, OllamaEmbeddings, OpenAiEmbeddings,
 };
+#[cfg(feature = "lancedb")]
+pub use lancedb_store::{DEFAULT_EMBEDDING_DIM, LanceDbVectorStore};
 #[cfg(feature = "postgres")]
 pub use repository::Repository;
 pub use search::{RankedResult, SearchConfig, SearchResult, reciprocal_rank_fusion};
+pub use vector_store::VectorStore;
 
 use std::sync::Arc;
 
@@ -332,6 +338,12 @@ pub struct Workspace {
     storage: WorkspaceStorage,
     /// Embedding provider for semantic search.
     embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    /// Optional external vector store for semantic search.
+    ///
+    /// When set, embeddings are stored here instead of (or in addition to)
+    /// the database's built-in vector support, and hybrid search uses this
+    /// for the vector component while FTS comes from the database.
+    vector_store: Option<Arc<dyn VectorStore>>,
 }
 
 impl Workspace {
@@ -343,6 +355,7 @@ impl Workspace {
             agent_id: None,
             storage: WorkspaceStorage::Repo(Repository::new(pool)),
             embeddings: None,
+            vector_store: None,
         }
     }
 
@@ -355,6 +368,7 @@ impl Workspace {
             agent_id: None,
             storage: WorkspaceStorage::Db(db),
             embeddings: None,
+            vector_store: None,
         }
     }
 
@@ -370,6 +384,17 @@ impl Workspace {
         self
     }
 
+    /// Set an external vector store for semantic search.
+    ///
+    /// When set, vector operations (store/search/delete embeddings) use this
+    /// store instead of the database's built-in vector support. FTS continues
+    /// to use the database. Hybrid search combines FTS from the database with
+    /// vector results from this store via RRF.
+    pub fn with_vector_store(mut self, store: Arc<dyn VectorStore>) -> Self {
+        self.vector_store = Some(store);
+        self
+    }
+
     /// Get the user ID.
     pub fn user_id(&self) -> &str {
         &self.user_id
@@ -458,9 +483,21 @@ impl Workspace {
 
     /// Delete a file.
     ///
-    /// Also deletes associated chunks.
+    /// Also deletes associated chunks (from both DB and external vector store).
     pub async fn delete(&self, path: &str) -> Result<(), WorkspaceError> {
         let path = normalize_path(path);
+
+        // Clean up external vector store before DB cascade deletes chunks
+        if let Some(ref vs) = self.vector_store
+            && let Ok(doc) = self
+                .storage
+                .get_document_by_path(&self.user_id, self.agent_id, &path)
+                .await
+            && let Err(e) = vs.delete_embeddings(doc.id).await
+        {
+            tracing::warn!("Failed to delete embeddings from vector store: {}", e);
+        }
+
         self.storage
             .delete_document_by_path(&self.user_id, self.agent_id, &path)
             .await
@@ -565,11 +602,26 @@ impl Workspace {
     ///
     /// Daily logs are raw, append-only notes for the current day.
     pub async fn append_daily_log(&self, entry: &str) -> Result<(), WorkspaceError> {
-        let today = Utc::now().date_naive();
+        self.append_daily_log_tz(entry, chrono_tz::Tz::UTC)
+            .await
+            .map(|_| ())
+    }
+
+    /// Append an entry to today's daily log using the given timezone.
+    ///
+    /// Returns the path that was written to (e.g. `daily/2024-01-15.md`).
+    pub async fn append_daily_log_tz(
+        &self,
+        entry: &str,
+        tz: chrono_tz::Tz,
+    ) -> Result<String, WorkspaceError> {
+        let now = crate::timezone::now_in_tz(tz);
+        let today = now.date_naive();
         let path = format!("daily/{}.md", today.format("%Y-%m-%d"));
-        let timestamp = Utc::now().format("%H:%M:%S");
+        let timestamp = now.format("%H:%M:%S");
         let timestamped_entry = format!("[{}] {}", timestamp, entry);
-        self.append(&path, &timestamped_entry).await
+        self.append(&path, &timestamped_entry).await?;
+        Ok(path)
     }
 
     // ==================== System Prompt ====================
@@ -584,6 +636,18 @@ impl Workspace {
         self.system_prompt_for_context(false).await
     }
 
+    /// Build the system prompt with timezone-aware daily log dates.
+    ///
+    /// Uses the given timezone to determine "today" and "yesterday" for daily log injection.
+    pub async fn system_prompt_for_context_tz(
+        &self,
+        is_group_chat: bool,
+        tz: chrono_tz::Tz,
+    ) -> Result<String, WorkspaceError> {
+        self.system_prompt_for_context_inner(is_group_chat, Some(tz))
+            .await
+    }
+
     /// Build the system prompt, optionally excluding personal memory.
     ///
     /// When `is_group_chat` is true, MEMORY.md is excluded to prevent
@@ -591,6 +655,16 @@ impl Workspace {
     pub async fn system_prompt_for_context(
         &self,
         is_group_chat: bool,
+    ) -> Result<String, WorkspaceError> {
+        self.system_prompt_for_context_inner(is_group_chat, None)
+            .await
+    }
+
+    /// Inner implementation for system prompt building.
+    async fn system_prompt_for_context_inner(
+        &self,
+        is_group_chat: bool,
+        tz: Option<chrono_tz::Tz>,
     ) -> Result<String, WorkspaceError> {
         let mut parts = Vec::new();
 
@@ -645,7 +719,10 @@ impl Workspace {
         }
 
         // Add today's memory context (last 2 days of daily logs)
-        let today = Utc::now().date_naive();
+        let today = match tz {
+            Some(t) => crate::timezone::today_in_tz(t),
+            None => Utc::now().date_naive(),
+        };
         let yesterday = today.pred_opt().unwrap_or(today);
 
         for date in [today, yesterday] {
@@ -685,20 +762,67 @@ impl Workspace {
         query: &str,
         config: SearchConfig,
     ) -> Result<Vec<SearchResult>, WorkspaceError> {
-        // Generate embedding for semantic search if provider available
-        let embedding = if let Some(ref provider) = self.embeddings {
-            Some(
-                provider
-                    .embed(query)
-                    .await
-                    .map_err(|e| WorkspaceError::EmbeddingFailed {
-                        reason: e.to_string(),
-                    })?,
-            )
-        } else {
-            None
-        };
+        // Generate embedding for semantic search only when vector search is enabled
+        let embedding =
+            if config.use_vector {
+                if let Some(ref provider) = self.embeddings {
+                    Some(provider.embed(query).await.map_err(|e| {
+                        WorkspaceError::EmbeddingFailed {
+                            reason: e.to_string(),
+                        }
+                    })?)
+                } else {
+                    None
+                }
+            } else {
+                None
+            };
 
+        // When an external vector store is configured, do FTS from the
+        // database and vector search from the store, then fuse with RRF.
+        if let Some(ref vs) = self.vector_store {
+            // FTS from database (disable vector to avoid double-searching)
+            let fts_results = if config.use_fts {
+                let fts_config = SearchConfig {
+                    use_fts: true,
+                    use_vector: false,
+                    ..config.clone()
+                };
+                let fts_search = self
+                    .storage
+                    .hybrid_search(&self.user_id, self.agent_id, query, None, &fts_config)
+                    .await?;
+                fts_search
+                    .into_iter()
+                    .enumerate()
+                    .map(|(i, r)| RankedResult {
+                        chunk_id: r.chunk_id,
+                        document_id: r.document_id,
+                        document_path: r.document_path,
+                        content: r.content,
+                        rank: (i + 1) as u32,
+                    })
+                    .collect()
+            } else {
+                Vec::new()
+            };
+
+            // Vector search from external store
+            let vector_results = if config.use_vector {
+                if let Some(ref emb) = embedding {
+                    vs.vector_search(&self.user_id, self.agent_id, emb, config.pre_fusion_limit)
+                        .await?
+                } else {
+                    Vec::new()
+                }
+            } else {
+                Vec::new()
+            };
+
+            return Ok(reciprocal_rank_fusion(fts_results, vector_results, &config));
+        }
+
+        // No external vector store — use database's built-in hybrid search
         self.storage
             .hybrid_search(
                 &self.user_id,
@@ -720,7 +844,13 @@ impl Workspace {
         // Chunk the content
         let chunks = chunk_document(&doc.content, ChunkConfig::default());
 
-        // Delete old chunks
+        // Delete old embeddings from external vector store FIRST — if this fails,
+        // we abort before touching DB chunks, keeping the document consistent.
+        if let Some(ref vs) = self.vector_store {
+            vs.delete_embeddings(document_id).await?;
+        }
+
+        // Delete old chunks from database
         self.storage.delete_chunks(document_id).await?;
 
         // Insert new chunks
@@ -738,9 +868,33 @@ impl Workspace {
                 None
             };
 
-            self.storage
-                .insert_chunk(document_id, index as i32, &content, embedding.as_deref())
+            // When an external vector store is active, skip writing embeddings
+            // to the DB (they'd never be queried from there).
+            let db_embedding = if self.vector_store.is_some() {
+                None
+            } else {
+                embedding.as_deref()
+            };
+
+            let chunk_id = self
+                .storage
+                .insert_chunk(document_id, index as i32, &content, db_embedding)
                 .await?;
+
+            // Sync embedding to external vector store (propagate errors to
+            // avoid leaving a document with deleted-then-missing embeddings).
+            if let (Some(vs), Some(emb)) = (&self.vector_store, &embedding) {
+                vs.store_embedding(
+                    chunk_id,
+                    document_id,
+                    &doc.path,
+                    &doc.user_id,
+                    doc.agent_id,
+                    &content,
+                    emb,
+                )
+                .await?;
+            }
         }
 
         Ok(())
@@ -985,6 +1139,23 @@ impl Workspace {
             .get_chunks_without_embeddings(&self.user_id, self.agent_id, 100)
             .await?;
 
+        // Prefetch document metadata to avoid N+1 queries when syncing to vector store
+        let doc_map: std::collections::HashMap<Uuid, crate::workspace::document::MemoryDocument> =
+            if self.vector_store.is_some() {
+                let mut map = std::collections::HashMap::new();
+                for chunk in &chunks {
+                    if !map.contains_key(&chunk.document_id)
+                        && let Ok(doc) =
+                            self.storage.get_document_by_id(chunk.document_id).await
+                    {
+                        map.insert(doc.id, doc);
+                    }
+                }
+                map
+            } else {
+                std::collections::HashMap::new()
+            };
+
         let mut count = 0;
         for chunk in chunks {
             match provider.embed(&chunk.content).await {
@@ -992,6 +1163,29 @@ impl Workspace {
                     self.storage
                         .update_chunk_embedding(chunk.id, &embedding)
                         .await?;
+
+                    // Sync to external vector store
+                    if let Some(ref vs) = self.vector_store
+                        && let Some(doc) = doc_map.get(&chunk.document_id)
+                        && let Err(e) = vs
+                            .update_embedding(
+                                chunk.id,
+                                chunk.document_id,
+                                &doc.path,
+                                &doc.user_id,
+                                doc.agent_id,
+                                &chunk.content,
+                                &embedding,
+                            )
+                            .await
+                    {
+                        tracing::warn!(
+                            "Failed to sync embedding to vector store for chunk {}: {}",
+                            chunk.id,
+                            e
+                        );
+                    }
+
                     count += 1;
                 }
                 Err(e) => {

src/workspace/vector_store.rs

@@ -0,0 +1,71 @@
+//! Vector store abstraction for workspace semantic search.
+//!
+//! Separates vector search from the main `Database` trait so that
+//! third-party vector backends (LanceDB, Qdrant, Pinecone, etc.) can
+//! be added by implementing a 4-method trait instead of wrapping the
+//! entire ~80-method `Database` trait.
+//!
+//! When no external vector store is configured, the built-in database
+//! vector support (pgvector / libsql_vector_idx) is used via the
+//! `Database::hybrid_search` method directly.
+
+use async_trait::async_trait;
+use uuid::Uuid;
+
+use crate::error::WorkspaceError;
+use crate::workspace::search::RankedResult;
+
+/// External vector store for semantic search.
+///
+/// Implementations hold chunk embeddings and perform vector similarity
+/// queries. Document/chunk metadata and FTS stay in the main database;
+/// only embeddings live here.
+///
+/// # Adding a new backend
+///
+/// 1. Implement this trait for your backend (4 methods).
+/// 2. Feature-gate the module (`#[cfg(feature = "mybackend")]`).
+/// 3. Pass `Arc<dyn VectorStore>` to `Workspace::with_vector_store()`.
+///
+/// That's it — no Database wrapper, no delegation boilerplate.
+#[async_trait]
+#[allow(clippy::too_many_arguments)]
+pub trait VectorStore: Send + Sync {
+    /// Store an embedding for a chunk.
+    async fn store_embedding(
+        &self,
+        chunk_id: Uuid,
+        document_id: Uuid,
+        document_path: &str,
+        user_id: &str,
+        agent_id: Option<Uuid>,
+        content: &str,
+        embedding: &[f32],
+    ) -> Result<(), WorkspaceError>;
+
+    /// Update an existing chunk's embedding (delete + re-insert is fine).
+    async fn update_embedding(
+        &self,
+        chunk_id: Uuid,
+        document_id: Uuid,
+        document_path: &str,
+        user_id: &str,
+        agent_id: Option<Uuid>,
+        content: &str,
+        embedding: &[f32],
+    ) -> Result<(), WorkspaceError>;
+
+    /// Delete all embeddings for a document.
+    async fn delete_embeddings(&self, document_id: Uuid) -> Result<(), WorkspaceError>;
+
+    /// Vector similarity search, filtered by user and optional agent.
+    ///
+    /// Returns results ranked by similarity (rank 1 = most similar).
+    async fn vector_search(
+        &self,
+        user_id: &str,
+        agent_id: Option<Uuid>,
+        embedding: &[f32],
+        limit: usize,
+    ) -> Result<Vec<RankedResult>, WorkspaceError>;
+}

tests/e2e_builtin_tool_coverage.rs

@@ -242,6 +242,16 @@ mod tests {
             "create_job should return a job_id: {:?}",
             create_result.1
         );
+        assert!(
+            create_result.1.contains("in_progress"),
+            "create_job should dispatch through the scheduler, not stay pending: {:?}",
+            create_result.1
+        );
+        assert!(
+            !create_result.1.contains("scheduler unavailable"),
+            "create_job should not fall back to the unscheduled path: {:?}",
+            create_result.1
+        );
         let status_result = results
             .iter()
             .find(|(n, _)| n == "job_status")

tests/e2e_routine_heartbeat.rs

@@ -20,9 +20,8 @@ mod tests {
     use ironclaw::agent::routine_engine::RoutineEngine;
     use ironclaw::agent::{HeartbeatConfig, HeartbeatRunner};
     use ironclaw::channels::IncomingMessage;
-    use ironclaw::config::{RoutineConfig, SafetyConfig};
+    use ironclaw::config::RoutineConfig;
     use ironclaw::db::Database;
-    use ironclaw::safety::SafetyLayer;
     use ironclaw::workspace::Workspace;
     use ironclaw::workspace::hygiene::HygieneConfig;
 
@@ -118,6 +117,7 @@ mod tests {
             "cron-test",
             Trigger::Cron {
                 schedule: "* * * * *".to_string(),
+                timezone: None,
             },
             "Check system status.",
         );
@@ -203,6 +203,7 @@ mod tests {
             thread_id: None,
             received_at: Utc::now(),
             metadata: serde_json::json!({}),
+            timezone: None,
             attachments: Vec::new(),
         };
         let fired = engine.check_event_triggers(&matching_msg).await;
@@ -224,6 +225,7 @@ mod tests {
             thread_id: None,
             received_at: Utc::now(),
             metadata: serde_json::json!({}),
+            timezone: None,
             attachments: Vec::new(),
         };
         let fired_neg = engine.check_event_triggers(&non_matching_msg).await;
@@ -288,6 +290,7 @@ mod tests {
             thread_id: None,
             received_at: Utc::now(),
             metadata: serde_json::json!({}),
+            timezone: None,
             attachments: Vec::new(),
         };
         let fired1 = engine.check_event_triggers(&msg).await;
@@ -342,10 +345,6 @@ mod tests {
             }],
         );
         let llm = Arc::new(TraceLlm::from_trace(trace));
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
 
         let (tx, mut rx) = tokio::sync::mpsc::channel(16);
 
@@ -357,9 +356,8 @@ mod tests {
             state_dir: _tmp.path().to_path_buf(),
         };
 
-        let runner =
-            HeartbeatRunner::new(HeartbeatConfig::default(), hygiene_config, ws, llm, safety)
-                .with_response_channel(tx);
+        let runner = HeartbeatRunner::new(HeartbeatConfig::default(), hygiene_config, ws, llm)
+            .with_response_channel(tx);
 
         let result = runner.check_heartbeat().await;
         match result {
@@ -396,10 +394,6 @@ mod tests {
         // LLM should NOT be called, so provide a trace that would panic if called.
         let trace = LlmTrace::single_turn("test-heartbeat-skip", "skip", vec![]);
         let llm = Arc::new(TraceLlm::from_trace(trace));
-        let safety = Arc::new(SafetyLayer::new(&SafetyConfig {
-            max_output_length: 100_000,
-            injection_check_enabled: false,
-        }));
 
         let hygiene_config = HygieneConfig {
             enabled: false,
@@ -409,8 +403,7 @@ mod tests {
             state_dir: _tmp.path().to_path_buf(),
         };
 
-        let runner =
-            HeartbeatRunner::new(HeartbeatConfig::default(), hygiene_config, ws, llm, safety);
+        let runner = HeartbeatRunner::new(HeartbeatConfig::default(), hygiene_config, ws, llm);
 
         let result = runner.check_heartbeat().await;
         assert!(

tests/heartbeat_integration.rs

@@ -15,7 +15,6 @@ use ironclaw::{
     config::Config,
     history::Store,
     llm::{create_llm_provider, create_session_manager},
-    safety::SafetyLayer,
     workspace::Workspace,
 };
 
@@ -93,8 +92,7 @@ async fn test_heartbeat_end_to_end() {
 
     let hb_config = ironclaw::agent::HeartbeatConfig::default();
     let hygiene_config = ironclaw::workspace::hygiene::HygieneConfig::default();
-    let safety = Arc::new(SafetyLayer::new(&config.safety));
-    let runner = HeartbeatRunner::new(hb_config, hygiene_config, workspace, llm, safety);
+    let runner = HeartbeatRunner::new(hb_config, hygiene_config, workspace, llm);
 
     let result = runner.check_heartbeat().await;
 

tests/lancedb_integration.rs

@@ -0,0 +1,123 @@
+//! Integration tests for LanceDB vector store with Workspace composition.
+//!
+//! Requires: cargo test --features "libsql,lancedb"
+//!
+//! Verifies that Workspace correctly composes FTS from libSQL with vector
+//! search from LanceDB via the VectorStore trait.
+
+#![cfg(all(feature = "libsql", feature = "lancedb"))]
+
+use std::sync::Arc;
+
+use ironclaw::db::Database;
+use ironclaw::db::libsql::LibSqlBackend;
+use ironclaw::workspace::{LanceDbVectorStore, SearchConfig, Workspace};
+use tempfile::TempDir;
+
+const EMBEDDING_DIM: usize = 1536;
+
+fn make_embedding(seed: f32) -> Vec<f32> {
+    (0..EMBEDDING_DIM)
+        .map(|i| (seed * (i as f32 + 1.0)).sin())
+        .collect()
+}
+
+/// Mock embedding provider that returns deterministic embeddings.
+struct FixedEmbeddings {
+    embedding: Vec<f32>,
+}
+
+#[async_trait::async_trait]
+impl ironclaw::workspace::EmbeddingProvider for FixedEmbeddings {
+    fn dimension(&self) -> usize {
+        EMBEDDING_DIM
+    }
+
+    fn model_name(&self) -> &str {
+        "fixed-test"
+    }
+
+    fn max_input_length(&self) -> usize {
+        8192
+    }
+
+    async fn embed(
+        &self,
+        _text: &str,
+    ) -> Result<Vec<f32>, ironclaw::workspace::embeddings::EmbeddingError> {
+        Ok(self.embedding.clone())
+    }
+}
+
+async fn setup_workspace() -> (Workspace, TempDir, TempDir) {
+    // Use a temp file (not :memory:) because libSQL in-memory DBs are connection-local
+    let db_dir = TempDir::new().unwrap();
+    let db_path = db_dir.path().join("test.db");
+    let libsql = LibSqlBackend::new_local(&db_path).await.unwrap();
+    libsql.run_migrations().await.unwrap();
+
+    let lancedb_dir = TempDir::new().unwrap();
+    let store = LanceDbVectorStore::new(lancedb_dir.path(), None).await.unwrap();
+
+    let embedding = make_embedding(1.0);
+    let ws = Workspace::new_with_db("test_user", Arc::new(libsql) as Arc<dyn Database>)
+        .with_vector_store(Arc::new(store))
+        .with_embeddings(Arc::new(FixedEmbeddings { embedding }));
+
+    (ws, lancedb_dir, db_dir)
+}
+
+#[tokio::test]
+async fn test_workspace_hybrid_search_with_lancedb() {
+    let (ws, _keep_lance, _keep_db) = setup_workspace().await;
+
+    // Write a document — this triggers chunking + embedding + LanceDB sync
+    ws.write(
+        "context/rust.md",
+        "Rust is a systems programming language focused on safety.",
+    )
+    .await
+    .unwrap();
+
+    // Hybrid search: FTS for "Rust" + vector from LanceDB
+    let results = ws.search("Rust", 5).await.unwrap();
+
+    assert!(!results.is_empty(), "hybrid search should return results");
+    assert!(results[0].content.contains("Rust"));
+}
+
+#[tokio::test]
+async fn test_workspace_delete_removes_from_lancedb() {
+    let (ws, _keep_lance, _keep_db) = setup_workspace().await;
+
+    ws.write("notes/deleted.md", "Content to be deleted.")
+        .await
+        .unwrap();
+
+    let before = ws.search("deleted", 5).await.unwrap();
+    assert_eq!(before.len(), 1);
+
+    ws.delete("notes/deleted.md").await.unwrap();
+
+    let after = ws.search("deleted", 5).await.unwrap();
+    assert!(after.is_empty());
+}
+
+#[tokio::test]
+async fn test_workspace_vector_only_search_uses_lancedb() {
+    let (ws, _keep_lance, _keep_db) = setup_workspace().await;
+
+    ws.write("sync/test.md", "Semantic content for vector search")
+        .await
+        .unwrap();
+
+    // Vector-only search should find via LanceDB even with non-matching FTS query
+    let config = SearchConfig::default().vector_only().with_limit(5);
+    let results = ws
+        .search_with_config("nonexistent_fts_term", config)
+        .await
+        .unwrap();
+
+    assert_eq!(results.len(), 1);
+    assert!(results[0].content.contains("Semantic content"));
+}

tests/support/test_rig.rs

@@ -545,16 +545,14 @@ impl TestRigBuilder {
             .await
             .expect("AppBuilder::build_all() failed in test rig");
 
+        let scheduler_slot: ironclaw::tools::builtin::SchedulerSlot =
+            Arc::new(tokio::sync::RwLock::new(None));
+
         // 6. Register job tools, routine tools, and extra tools.
         {
-            use ironclaw::context::ContextManager;
-
-            let ctx_mgr = Arc::new(ContextManager::new(
-                components.config.agent.max_parallel_jobs,
-            ));
             components.tools.register_job_tools(
-                ctx_mgr,
-                None,
+                Arc::clone(&components.context_manager),
+                Some(scheduler_slot.clone()),
                 None,
                 components.db.clone(),
                 None,
@@ -657,10 +655,13 @@ impl TestRigBuilder {
             None, // heartbeat_config
             None, // hygiene_config
             routine_config,
-            None, // context_manager
+            Some(Arc::clone(&components.context_manager)),
             None, // session_manager
         );
 
+        // Match main.rs: fill the scheduler slot once Agent::new has created it.
+        *scheduler_slot.write().await = Some(agent.scheduler());
+
         // 9. Spawn agent in background task.
         let agent_handle = tokio::spawn(async move {
             if let Err(e) = agent.run().await {

tests/support/trace_llm.rs

@@ -513,32 +513,41 @@ impl LlmProvider for TraceLlm {
     }
 
     async fn complete(&self, request: CompletionRequest) -> Result<CompletionResponse, LlmError> {
-        let step = self.next_step(&request.messages)?;
-        match step.response {
-            TraceResponse::Text {
-                content,
-                input_tokens,
-                output_tokens,
-            } => Ok(CompletionResponse {
-                content,
-                input_tokens,
-                output_tokens,
-                finish_reason: FinishReason::Stop,
-                cache_read_input_tokens: 0,
-                cache_creation_input_tokens: 0,
-            }),
-            TraceResponse::ToolCalls { .. } => Err(LlmError::RequestFailed {
-                provider: self.model_name.clone(),
-                reason: "TraceLlm::complete() called but current step is a tool_calls response; \
-                         use complete_with_tools() instead"
-                    .to_string(),
-            }),
-            TraceResponse::UserInput { .. } => Err(LlmError::RequestFailed {
-                provider: self.model_name.clone(),
-                reason: "TraceLlm::complete() encountered a user_input step; \
-                         these should have been filtered out during construction"
-                    .to_string(),
-            }),
+        // complete() is called when Reasoning has force_text=true (no tools
+        // available). Skip any remaining ToolCalls steps in the trace and
+        // return the next Text step, since in real usage the LLM would
+        // produce text when no tools are offered.
+        loop {
+            let step = self.next_step(&request.messages)?;
+            match step.response {
+                TraceResponse::Text {
+                    content,
+                    input_tokens,
+                    output_tokens,
+                } => {
+                    return Ok(CompletionResponse {
+                        content,
+                        input_tokens,
+                        output_tokens,
+                        finish_reason: FinishReason::Stop,
+                        cache_read_input_tokens: 0,
+                        cache_creation_input_tokens: 0,
+                    });
+                }
+                TraceResponse::ToolCalls { .. } => {
+                    // Skip tool_calls steps — complete() is called in
+                    // force_text mode so the LLM can't use tools anyway.
+                    continue;
+                }
+                TraceResponse::UserInput { .. } => {
+                    return Err(LlmError::RequestFailed {
+                        provider: self.model_name.clone(),
+                        reason: "TraceLlm::complete() encountered a user_input step; \
+                                 these should have been filtered out during construction"
+                            .to_string(),
+                    });
+                }
+            }
         }
     }
 

tests/support_unit_tests.rs

@@ -571,22 +571,29 @@ mod trace_llm_tests {
     }
 
     #[tokio::test]
-    async fn complete_errors_on_tool_calls_step() {
+    async fn complete_skips_tool_calls_step() {
+        // complete() is called in force_text mode where tools aren't available.
+        // When the trace has a ToolCalls step followed by a Text step, complete()
+        // should skip the ToolCalls and return the Text response.
         let trace = LlmTrace::single_turn(
             "test-model",
             "hi",
-            vec![tool_calls_step(vec![simple_tool_call("echo")], 10, 5)],
+            vec![
+                tool_calls_step(vec![simple_tool_call("echo")], 10, 5),
+                text_step("skipped past tools", 20, 8),
+            ],
         );
         let llm = TraceLlm::from_trace(trace);
 
-        let result = llm.complete(make_completion_request("hi")).await;
+        let resp = llm
+            .complete(make_completion_request("hi"))
+            .await
+            .expect("complete() should skip ToolCalls and return the Text step");
 
-        assert!(result.is_err());
-        let err_msg = result.unwrap_err().to_string();
-        assert!(
-            err_msg.contains("tool_calls"),
-            "Expected 'tool_calls' in error: {err_msg}"
-        );
+        assert_eq!(resp.content, "skipped past tools");
+        assert_eq!(resp.input_tokens, 20);
+        assert_eq!(resp.output_tokens, 8);
+        assert_eq!(resp.finish_reason, FinishReason::Stop);
     }
 
     #[tokio::test]