Merge pull request #1645 from nearai/staging-promote/0341fcc9-23558273569

chore: promote staging to staging-promote/6daa2f15-23538193544 (2026-03-25 18:47 UTC)

.github/workflows/test.yml

@@ -12,6 +12,7 @@ jobs:
   tests:
     name: Tests (${{ matrix.name }})
     runs-on: ubuntu-latest
+    timeout-minutes: 45
     strategy:
       fail-fast: false
       matrix:
@@ -40,11 +41,14 @@ jobs:
       - name: Build WASM channels (for integration tests)
         run: ./scripts/build-wasm-extensions.sh --channels
       - name: Run Tests
-        run: cargo test ${{ matrix.flags }} -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 40m \
+            cargo test ${{ matrix.flags }} -- --nocapture
 
   heavy-integration-tests:
     name: Heavy Integration Tests
     runs-on: ubuntu-latest
+    timeout-minutes: 20
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
@@ -58,9 +62,13 @@ jobs:
       - name: Build Telegram WASM channel
         run: cargo build --manifest-path channels-src/telegram/Cargo.toml --target wasm32-wasip2 --release
       - name: Run thread scheduling integration tests
-        run: cargo test --no-default-features --features libsql,integration --test e2e_thread_scheduling -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 15m \
+            cargo test --no-default-features --features libsql,integration --test e2e_thread_scheduling -- --nocapture
       - name: Run Telegram thread-scope regression test
-        run: cargo test --features integration --test telegram_auth_integration test_private_messages_use_chat_id_as_thread_scope -- --exact
+        run: |
+          timeout --signal=INT --kill-after=30s 10m \
+            cargo test --features integration --test telegram_auth_integration test_private_messages_use_chat_id_as_thread_scope -- --exact
 
   telegram-tests:
     name: Telegram Channel Tests
@@ -68,6 +76,7 @@ jobs:
       github.event_name != 'pull_request' ||
       github.base_ref != 'staging'
     runs-on: ubuntu-latest
+    timeout-minutes: 15
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
@@ -75,7 +84,9 @@ jobs:
         uses: dtolnay/rust-toolchain@stable
       - uses: Swatinem/rust-cache@v2
       - name: Run Telegram Channel Tests
-        run: cargo test --manifest-path channels-src/telegram/Cargo.toml -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 10m \
+            cargo test --manifest-path channels-src/telegram/Cargo.toml -- --nocapture
 
   windows-build:
     name: Windows Build (${{ matrix.name }})
@@ -110,6 +121,7 @@ jobs:
       github.event_name != 'pull_request' ||
       github.base_ref != 'staging'
     runs-on: ubuntu-latest
+    timeout-minutes: 30
     steps:
       - name: Checkout repository
         uses: actions/checkout@v6
@@ -125,7 +137,9 @@ jobs:
       - name: Build all WASM extensions against current WIT
         run: ./scripts/build-wasm-extensions.sh
       - name: Instantiation test (host linker compatibility)
-        run: cargo test --all-features wit_compat -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 20m \
+            cargo test --all-features wit_compat -- --nocapture
 
   bench-compile:
     name: Benchmark Compilation

crates/ironclaw_common/src/event.rs

@@ -7,6 +7,32 @@
 
 use serde::{Deserialize, Serialize};
 
+/// A single tool decision in a reasoning update (SSE DTO).
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ToolDecisionDto {
+    pub tool_name: String,
+    pub rationale: String,
+}
+
+impl ToolDecisionDto {
+    /// Parse a list of tool decisions from a JSON array value.
+    pub fn from_json_array(value: &serde_json::Value) -> Vec<Self> {
+        value
+            .as_array()
+            .map(|arr| {
+                arr.iter()
+                    .filter_map(|d| {
+                        Some(Self {
+                            tool_name: d.get("tool_name")?.as_str()?.to_string(),
+                            rationale: d.get("rationale")?.as_str()?.to_string(),
+                        })
+                    })
+                    .collect()
+            })
+            .unwrap_or_default()
+    }
+}
+
 #[derive(Debug, Clone, Serialize, Deserialize)]
 #[serde(tag = "type")]
 pub enum AppEvent {
@@ -163,6 +189,23 @@ pub enum AppEvent {
         #[serde(skip_serializing_if = "Option::is_none")]
         message: Option<String>,
     },
+
+    /// Agent reasoning update (why it chose specific tools).
+    #[serde(rename = "reasoning_update")]
+    ReasoningUpdate {
+        narrative: String,
+        decisions: Vec<ToolDecisionDto>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+
+    /// Reasoning update for a sandbox job.
+    #[serde(rename = "job_reasoning")]
+    JobReasoning {
+        job_id: String,
+        narrative: String,
+        decisions: Vec<ToolDecisionDto>,
+    },
 }
 
 impl AppEvent {
@@ -191,6 +234,8 @@ impl AppEvent {
             Self::Suggestions { .. } => "suggestions",
             Self::TurnCost { .. } => "turn_cost",
             Self::ExtensionStatus { .. } => "extension_status",
+            Self::ReasoningUpdate { .. } => "reasoning_update",
+            Self::JobReasoning { .. } => "job_reasoning",
         }
     }
 }
@@ -311,6 +356,16 @@ mod tests {
                 status: String::new(),
                 message: None,
             },
+            AppEvent::ReasoningUpdate {
+                narrative: String::new(),
+                decisions: vec![],
+                thread_id: None,
+            },
+            AppEvent::JobReasoning {
+                job_id: String::new(),
+                narrative: String::new(),
+                decisions: vec![],
+            },
         ];
 
         for variant in &variants {

crates/ironclaw_common/src/lib.rs

@@ -3,5 +3,5 @@
 mod event;
 mod util;
 
-pub use event::AppEvent;
+pub use event::{AppEvent, ToolDecisionDto};
 pub use util::truncate_preview;

src/agent/agent_loop.rs

@@ -16,6 +16,7 @@ use crate::agent::context_monitor::ContextMonitor;
 use crate::agent::heartbeat::spawn_heartbeat;
 use crate::agent::routine_engine::{RoutineEngine, spawn_cron_ticker};
 use crate::agent::self_repair::{DefaultSelfRepair, RepairResult, SelfRepair};
+use crate::agent::session::ThreadState;
 use crate::agent::session_manager::SessionManager;
 use crate::agent::submission::{Submission, SubmissionParser, SubmissionResult};
 use crate::agent::{HeartbeatConfig as AgentHeartbeatConfig, Router, Scheduler, SchedulerDeps};
@@ -84,6 +85,15 @@ fn resolve_owner_scope_notification_user(
     trimmed_option(explicit_user).or_else(|| trimmed_option(owner_fallback))
 }
 
+fn is_single_message_repl(message: &IncomingMessage) -> bool {
+    message.channel == "repl"
+        && message
+            .metadata
+            .get("single_message_mode")
+            .and_then(|value| value.as_bool())
+            .unwrap_or(false)
+}
+
 async fn resolve_channel_notification_user(
     extension_manager: Option<&Arc<ExtensionManager>>,
     channel: Option<&str>,
@@ -1140,9 +1150,14 @@ impl Agent {
             && let Submission::UserInput { ref content } = submission
             && let Some(engine) = self.routine_engine().await
         {
+            let single_message_repl = is_single_message_repl(message);
             // Use post-hook content so that BeforeInbound hooks that rewrite
             // input are respected by event trigger matching.
-            let fired = engine.check_event_triggers(message, content).await;
+            let fired = if single_message_repl {
+                engine.check_event_triggers_and_wait(message, content).await
+            } else {
+                engine.check_event_triggers(message, content).await
+            };
             if fired > 0 {
                 tracing::debug!(
                     channel = %message.channel,
@@ -1150,10 +1165,16 @@ impl Agent {
                     fired,
                     "Consumed inbound user message with matching event-triggered routine(s)"
                 );
-                return Ok(Some(String::new()));
+                return if single_message_repl {
+                    Ok(None)
+                } else {
+                    Ok(Some(String::new()))
+                };
             }
         }
 
+        let session_for_empty_exit = Arc::clone(&session);
+
         // Process based on submission type
         let result = match submission {
             Submission::UserInput { content } => {
@@ -1250,6 +1271,28 @@ impl Agent {
                     command,
                     message.channel
                 );
+                // /reasoning is special-cased here (not in handle_system_command)
+                // because it needs the session + thread_id to read turn reasoning
+                // data, which handle_system_command's signature doesn't provide.
+                if command == "reasoning" {
+                    let result = self
+                        .handle_reasoning_command(&args, &session, thread_id)
+                        .await;
+                    return match result {
+                        SubmissionResult::Response { content } => Ok(Some(content)),
+                        SubmissionResult::Ok { message } => Ok(message),
+                        SubmissionResult::Error { message } => {
+                            Ok(Some(format!("Error: {}", message)))
+                        }
+                        _ => {
+                            if is_single_message_repl(message) {
+                                Ok(None)
+                            } else {
+                                Ok(Some(String::new()))
+                            }
+                        }
+                    };
+                }
                 // Authorization checks (including restart channel check) are enforced in handle_system_command
                 self.handle_system_command(&command, &args, &message.channel)
                     .await
@@ -1309,7 +1352,26 @@ impl Agent {
                     Ok(Some(content))
                 }
             }
-            SubmissionResult::Ok { message } => Ok(message),
+            SubmissionResult::Ok {
+                message: output_message,
+            } => {
+                let should_exit =
+                    if output_message.as_deref() == Some("") && is_single_message_repl(message) {
+                        let sess = session_for_empty_exit.lock().await;
+                        sess.threads
+                            .get(&thread_id)
+                            .map(|thread| thread.state != ThreadState::AwaitingApproval)
+                            .unwrap_or(true)
+                    } else {
+                        false
+                    };
+
+                if should_exit {
+                    Ok(None)
+                } else {
+                    Ok(output_message)
+                }
+            }
             SubmissionResult::Error { message } => Ok(Some(format!("Error: {}", message))),
             SubmissionResult::Interrupted => Ok(Some("Interrupted.".into())),
             SubmissionResult::NeedApproval { .. } => {
@@ -1325,7 +1387,7 @@ impl Agent {
 #[cfg(test)]
 mod tests {
     use super::{
-        chat_tool_execution_metadata, resolve_routine_notification_user,
+        chat_tool_execution_metadata, is_single_message_repl, resolve_routine_notification_user,
         should_fallback_routine_notification, truncate_for_preview,
     };
     use crate::channels::IncomingMessage;
@@ -1487,4 +1549,17 @@ mod tests {
 
         assert!(should_fallback_routine_notification(&error)); // safety: test-only assertion
     }
+
+    #[test]
+    fn single_message_repl_detection_requires_repl_channel_and_metadata_flag() {
+        let repl = IncomingMessage::new("repl", "owner-scope", "hello")
+            .with_metadata(serde_json::json!({ "single_message_mode": true }));
+        let gateway = IncomingMessage::new("gateway", "owner-scope", "hello")
+            .with_metadata(serde_json::json!({ "single_message_mode": true }));
+        let plain_repl = IncomingMessage::new("repl", "owner-scope", "hello");
+
+        assert!(is_single_message_repl(&repl)); // safety: test-only assertion
+        assert!(!is_single_message_repl(&gateway)); // safety: test-only assertion
+        assert!(!is_single_message_repl(&plain_repl)); // safety: test-only assertion
+    }
 }

src/agent/agentic_loop.rs

@@ -414,6 +414,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "echo".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
         let delegate = MockDelegate::new(vec![
             tool_calls_output(vec![tool_call]),

src/agent/commands.rs

@@ -465,6 +465,94 @@ impl Agent {
         }
     }
 
+    /// Handle `/reasoning [N|all]` — show reasoning history for the active thread.
+    pub(super) async fn handle_reasoning_command(
+        &self,
+        args: &[String],
+        session: &Arc<Mutex<Session>>,
+        thread_id: Uuid,
+    ) -> SubmissionResult {
+        // Clone the turn data we need, then drop the session lock.
+        let turns_snapshot: Vec<(
+            usize,
+            Option<String>,
+            Vec<crate::agent::session::TurnToolCall>,
+        )>;
+        {
+            let sess = session.lock().await;
+            let thread = match sess.threads.get(&thread_id) {
+                Some(t) => t,
+                None => return SubmissionResult::error("No active thread."),
+            };
+
+            if thread.turns.is_empty() {
+                return SubmissionResult::ok_with_message("No turns yet.");
+            }
+
+            // Parse argument: default=last turn, "all"=all turns, N=specific turn (1-based).
+            let selected: Vec<&crate::agent::session::Turn> = match args.first().map(|s| s.as_str())
+            {
+                Some("all") => thread.turns.iter().collect(),
+                Some(n) => match n.parse::<usize>() {
+                    Ok(0) => return SubmissionResult::error("Turn numbers start at 1."),
+                    Ok(num) if num > thread.turns.len() => {
+                        return SubmissionResult::error(format!(
+                            "Turn {} does not exist (max: {}).",
+                            num,
+                            thread.turns.len()
+                        ));
+                    }
+                    Ok(num) => vec![&thread.turns[num - 1]],
+                    Err(_) => return SubmissionResult::error("Usage: /reasoning [N|all]"),
+                },
+                None => {
+                    // Default: last turn that has tool calls
+                    match thread.turns.iter().rev().find(|t| !t.tool_calls.is_empty()) {
+                        Some(t) => vec![t],
+                        None => {
+                            return SubmissionResult::ok_with_message("No turns with tool calls.");
+                        }
+                    }
+                }
+            };
+
+            turns_snapshot = selected
+                .into_iter()
+                .map(|t| (t.turn_number, t.narrative.clone(), t.tool_calls.clone()))
+                .collect();
+        }
+        // Session lock is now dropped — format output without holding it.
+
+        let mut output = String::new();
+        for (turn_number, narrative, tool_calls) in &turns_snapshot {
+            output.push_str(&format!("--- Turn {} ---\n", turn_number + 1));
+            if let Some(narrative) = narrative {
+                output.push_str(&format!("Reasoning: {}\n", narrative));
+            }
+            if tool_calls.is_empty() {
+                output.push_str("  (no tool calls)\n");
+            } else {
+                for tc in tool_calls {
+                    let status = if tc.error.is_some() {
+                        "error"
+                    } else if tc.result.is_some() {
+                        "ok"
+                    } else {
+                        "pending"
+                    };
+                    output.push_str(&format!("  {} [{}]", tc.name, status));
+                    if let Some(ref rationale) = tc.rationale {
+                        output.push_str(&format!(" — {}", rationale));
+                    }
+                    output.push('\n');
+                }
+            }
+            output.push('\n');
+        }
+
+        SubmissionResult::response(output.trim_end())
+    }
+
     /// Handle system commands that bypass thread-state checks entirely.
     pub(super) async fn handle_system_command(
         &self,
@@ -480,6 +568,7 @@ impl Agent {
                 "  /version          Show version info\n",
                 "  /tools            List available tools\n",
                 "  /debug            Toggle debug mode\n",
+                "  /reasoning [N|all] Show agent reasoning for turns\n",
                 "  /ping             Connectivity check\n",
                 "\n",
                 "Jobs:\n",

src/agent/dispatcher.rs

@@ -63,7 +63,12 @@ impl Agent {
         );
 
         let system_prompt = if let Some(ws) = self.workspace() {
-            match ws
+            let scoped_workspace = if ws.user_id() == message.user_id {
+                Arc::clone(ws)
+            } else {
+                Arc::new(ws.scoped_to_user(&message.user_id))
+            };
+            match scoped_workspace
                 .system_prompt_for_context_tz(is_group_chat, user_tz)
                 .await
             {
@@ -420,6 +425,19 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
         content: Option<String>,
         reason_ctx: &mut ReasoningContext,
     ) -> Result<Option<LoopOutcome>, Error> {
+        // Extract and sanitize the narrative before consuming `content`.
+        let narrative = content
+            .as_deref()
+            .filter(|c| !c.trim().is_empty())
+            .map(|c| {
+                let sanitized = self
+                    .agent
+                    .safety()
+                    .sanitize_tool_output("agent_narrative", c);
+                sanitized.content
+            })
+            .filter(|c| !c.trim().is_empty());
+
         // Add the assistant message with tool_calls to context.
         // OpenAI protocol requires this before tool-result messages.
         reason_ctx
@@ -440,6 +458,41 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
             )
             .await;
 
+        // Build per-tool decisions for the reasoning update.
+        // Sanitize each rationale through SafetyLayer (parity with JobDelegate).
+        let decisions: Vec<crate::channels::ToolDecision> = tool_calls
+            .iter()
+            .filter_map(|tc| {
+                tc.reasoning.as_ref().map(|r| {
+                    let sanitized = self
+                        .agent
+                        .safety()
+                        .sanitize_tool_output("tool_rationale", r)
+                        .content;
+                    crate::channels::ToolDecision {
+                        tool_name: tc.name.clone(),
+                        rationale: sanitized,
+                    }
+                })
+            })
+            .collect();
+
+        // Emit reasoning update to channels.
+        if narrative.is_some() || !decisions.is_empty() {
+            let _ = self
+                .agent
+                .channels
+                .send_status(
+                    &self.message.channel,
+                    StatusUpdate::ReasoningUpdate {
+                        narrative: narrative.clone().unwrap_or_default(),
+                        decisions: decisions.clone(),
+                    },
+                    &self.message.metadata,
+                )
+                .await;
+        }
+
         // Record tool calls in the thread with sensitive params redacted.
         {
             let mut redacted_args: Vec<serde_json::Value> = Vec::with_capacity(tool_calls.len());
@@ -455,8 +508,23 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
             if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                 && let Some(turn) = thread.last_turn_mut()
             {
+                // Set turn-level narrative.
+                if turn.narrative.is_none() {
+                    turn.narrative = narrative;
+                }
                 for (tc, safe_args) in tool_calls.iter().zip(redacted_args) {
-                    turn.record_tool_call(&tc.name, safe_args);
+                    let sanitized_rationale = tc.reasoning.as_ref().map(|r| {
+                        self.agent
+                            .safety()
+                            .sanitize_tool_output("tool_rationale", r)
+                            .content
+                    });
+                    turn.record_tool_call_with_reasoning(
+                        &tc.name,
+                        safe_args,
+                        sanitized_rationale,
+                        Some(tc.id.clone()),
+                    );
                 }
             }
         }
@@ -726,7 +794,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                         if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                             && let Some(turn) = thread.last_turn_mut()
                         {
-                            turn.record_tool_error(error_msg.clone());
+                            turn.record_tool_error_for(&tc.id, error_msg.clone());
                         }
                     }
                     reason_ctx
@@ -852,16 +920,19 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                         Err(e) => format!("Tool '{}' failed: {}", tc.name, e),
                     };
 
-                    // Record sanitized result in thread
+                    // Record sanitized result in thread (identity-based matching).
                     {
                         let mut sess = self.session.lock().await;
                         if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                             && let Some(turn) = thread.last_turn_mut()
                         {
                             if is_tool_error {
-                                turn.record_tool_error(result_content.clone());
+                                turn.record_tool_error_for(&tc.id, result_content.clone());
                             } else {
-                                turn.record_tool_result(serde_json::json!(result_content));
+                                turn.record_tool_result_for(
+                                    &tc.id,
+                                    serde_json::json!(result_content),
+                                );
                             }
                         }
                     }
@@ -1462,11 +1533,13 @@ mod tests {
                     id: "call_2".to_string(),
                     name: "http".to_string(),
                     arguments: serde_json::json!({"url": "https://example.com"}),
+                    reasoning: None,
                 },
                 ToolCall {
                     id: "call_3".to_string(),
                     name: "echo".to_string(),
                     arguments: serde_json::json!({"message": "done"}),
+                    reasoning: None,
                 },
             ],
             user_timezone: None,
@@ -1652,6 +1725,7 @@ mod tests {
                     id: "call_1".to_string(),
                     name: "echo".to_string(),
                     arguments: serde_json::json!({"message": "hi"}),
+                    reasoning: None,
                 }],
             ),
             ChatMessage::tool_result("call_1", "echo", "hi"),
@@ -1744,11 +1818,13 @@ mod tests {
                         id: "c1".to_string(),
                         name: "http".to_string(),
                         arguments: serde_json::json!({}),
+                        reasoning: None,
                     },
                     ToolCall {
                         id: "c2".to_string(),
                         name: "echo".to_string(),
                         arguments: serde_json::json!({}),
+                        reasoning: None,
                     },
                 ],
             ),
@@ -1782,6 +1858,7 @@ mod tests {
                     id: "c1".to_string(),
                     name: "echo".to_string(),
                     arguments: serde_json::json!({}),
+                    reasoning: None,
                 }],
             ),
             ChatMessage::tool_result("c1", "echo", "done"),
@@ -1912,6 +1989,7 @@ mod tests {
                     id: crate::llm::generate_tool_call_id(0, 0),
                     name: "echo".to_string(),
                     arguments: serde_json::json!({"message": "looping"}),
+                    reasoning: None,
                 }],
                 input_tokens: 0,
                 output_tokens: 5,
@@ -2065,6 +2143,7 @@ mod tests {
                     id: crate::llm::generate_tool_call_id(0, 0),
                     name: "nonexistent_tool".to_string(),
                     arguments: serde_json::json!({}),
+                    reasoning: None,
                 }],
                 input_tokens: 0,
                 output_tokens: 5,

src/agent/routine_engine.rs

@@ -18,6 +18,7 @@ use std::time::Duration;
 use chrono::Utc;
 use regex::Regex;
 use tokio::sync::{RwLock, mpsc};
+use tokio::task::JoinHandle;
 use uuid::Uuid;
 
 use crate::agent::Scheduler;
@@ -45,6 +46,11 @@ enum EventMatcher {
     System { routine: Routine },
 }
 
+struct TriggeredRoutine {
+    routine: Routine,
+    detail: String,
+}
+
 /// Distinguishes why sandbox is unavailable so error messages are accurate.
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub enum SandboxReadiness {
@@ -202,6 +208,44 @@ impl RoutineEngine {
 
     /// Check incoming message against event triggers. Returns number of routines fired.
     pub async fn check_event_triggers(&self, message: &IncomingMessage, content: &str) -> usize {
+        let triggered = self.matching_event_triggers(message, content).await;
+        let fired = triggered.len();
+        for triggered in triggered {
+            std::mem::drop(self.spawn_fire(triggered.routine, "event", Some(triggered.detail)));
+        }
+        fired
+    }
+
+    /// Fire matching event-triggered routines and wait for them to complete.
+    ///
+    /// Used by single-message REPL mode so the process does not exit before
+    /// background event-triggered routines finish.
+    pub async fn check_event_triggers_and_wait(
+        &self,
+        message: &IncomingMessage,
+        content: &str,
+    ) -> usize {
+        let triggered = self.matching_event_triggers(message, content).await;
+        let fired = triggered.len();
+        let handles: Vec<JoinHandle<()>> = triggered
+            .into_iter()
+            .map(|triggered| self.spawn_fire(triggered.routine, "event", Some(triggered.detail)))
+            .collect();
+
+        for handle in handles {
+            if let Err(e) = handle.await {
+                tracing::warn!(error = %e, "Event-triggered routine task failed");
+            }
+        }
+
+        fired
+    }
+
+    async fn matching_event_triggers(
+        &self,
+        message: &IncomingMessage,
+        content: &str,
+    ) -> Vec<TriggeredRoutine> {
         let cache = self.event_cache.read().await;
 
         // Early return if there are no message matchers at all.
@@ -209,10 +253,9 @@ impl RoutineEngine {
             .iter()
             .any(|m| matches!(m, EventMatcher::Message { .. }))
         {
-            return 0;
+            return Vec::new();
         }
-
-        let mut fired = 0;
+        let mut triggered = Vec::new();
 
         // Collect routine IDs for batch query
         let routine_ids: Vec<Uuid> = cache
@@ -224,13 +267,13 @@ impl RoutineEngine {
             .collect();
 
         if routine_ids.is_empty() {
-            return 0;
+            return Vec::new();
         }
 
         // Single batch query instead of N queries
         let concurrent_counts = match self.batch_concurrent_counts(&routine_ids).await {
             Some(counts) => counts,
-            None => return 0,
+            None => return Vec::new(),
         };
 
         for matcher in cache.iter() {
@@ -285,11 +328,13 @@ impl RoutineEngine {
             }
 
             let detail = truncate(content, 200);
-            self.spawn_fire(routine.clone(), "event", Some(detail));
-            fired += 1;
+            triggered.push(TriggeredRoutine {
+                routine: routine.clone(),
+                detail,
+            });
         }
 
-        fired
+        triggered
     }
 
     /// Emit a structured event to system-event routines.
@@ -845,7 +890,12 @@ impl RoutineEngine {
     }
 
     /// Spawn a fire in a background task.
-    fn spawn_fire(&self, routine: Routine, trigger_type: &str, trigger_detail: Option<String>) {
+    fn spawn_fire(
+        &self,
+        routine: Routine,
+        trigger_type: &str,
+        trigger_detail: Option<String>,
+    ) -> JoinHandle<()> {
         let run = RoutineRun {
             id: Uuid::new_v4(),
             routine_id: routine.id,
@@ -882,7 +932,7 @@ impl RoutineEngine {
                 return;
             }
             execute_routine(engine, routine, run).await;
-        });
+        })
     }
 
     fn check_cooldown(&self, routine: &Routine) -> bool {

src/agent/session.rs

@@ -449,6 +449,7 @@ impl Thread {
                         id: call_id.clone(),
                         name: tc.name.clone(),
                         arguments: tc.parameters.clone(),
+                        reasoning: None,
                     })
                     .collect();
 
@@ -522,7 +523,12 @@ impl Thread {
                             && let Some(ref tcs) = assistant_msg.tool_calls
                         {
                             for tc in tcs {
-                                turn.record_tool_call(&tc.name, tc.arguments.clone());
+                                turn.record_tool_call_with_reasoning(
+                                    &tc.name,
+                                    tc.arguments.clone(),
+                                    tc.reasoning.clone(),
+                                    Some(tc.id.clone()),
+                                );
                             }
                         }
 
@@ -602,6 +608,10 @@ pub struct Turn {
     pub completed_at: Option<DateTime<Utc>>,
     /// Error message (if failed).
     pub error: Option<String>,
+    /// Agent's reasoning narrative for this turn.
+    /// Cleaned via `clean_response` and sanitized through `SafetyLayer` before storage.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub narrative: Option<String>,
     /// Transient image content parts for multimodal LLM input.
     /// Not serialized — images are only needed for the current LLM call.
     /// The text description in `user_input` persists for compaction/context.
@@ -621,6 +631,7 @@ impl Turn {
             started_at: Utc::now(),
             completed_at: None,
             error: None,
+            narrative: None,
             image_content_parts: Vec::new(),
         }
     }
@@ -656,6 +667,26 @@ impl Turn {
             parameters: params,
             result: None,
             error: None,
+            rationale: None,
+            tool_call_id: None,
+        });
+    }
+
+    /// Record a tool call with reasoning context.
+    pub fn record_tool_call_with_reasoning(
+        &mut self,
+        name: impl Into<String>,
+        params: serde_json::Value,
+        rationale: Option<String>,
+        tool_call_id: Option<String>,
+    ) {
+        self.tool_calls.push(TurnToolCall {
+            name: name.into(),
+            parameters: params,
+            result: None,
+            error: None,
+            rationale,
+            tool_call_id,
         });
     }
 
@@ -672,6 +703,60 @@ impl Turn {
             call.error = Some(error.into());
         }
     }
+
+    /// Record a tool result by tool_call_id, with fallback to first pending call.
+    pub fn record_tool_result_for(&mut self, tool_call_id: &str, result: serde_json::Value) {
+        if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.tool_call_id.as_deref() == Some(tool_call_id))
+        {
+            call.result = Some(result);
+        } else if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.result.is_none() && c.error.is_none())
+        {
+            tracing::debug!(
+                tool_call_id = %tool_call_id,
+                fallback_tool = %call.name,
+                "tool_call_id not found, falling back to first pending call"
+            );
+            call.result = Some(result);
+        } else {
+            tracing::warn!(
+                tool_call_id = %tool_call_id,
+                "Tool result dropped: no matching or pending tool call"
+            );
+        }
+    }
+
+    /// Record a tool error by tool_call_id, with fallback to first pending call.
+    pub fn record_tool_error_for(&mut self, tool_call_id: &str, error: impl Into<String>) {
+        if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.tool_call_id.as_deref() == Some(tool_call_id))
+        {
+            call.error = Some(error.into());
+        } else if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.result.is_none() && c.error.is_none())
+        {
+            tracing::debug!(
+                tool_call_id = %tool_call_id,
+                fallback_tool = %call.name,
+                "tool_call_id not found, falling back to first pending call"
+            );
+            call.error = Some(error.into());
+        } else {
+            tracing::warn!(
+                tool_call_id = %tool_call_id,
+                "Tool error dropped: no matching or pending tool call"
+            );
+        }
+    }
 }
 
 /// Record of a tool call made during a turn.
@@ -685,6 +770,12 @@ pub struct TurnToolCall {
     pub result: Option<serde_json::Value>,
     /// Error from the tool (if failed).
     pub error: Option<String>,
+    /// Agent's reasoning for choosing this tool.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub rationale: Option<String>,
+    /// The tool_call_id from the LLM, for identity-based result matching.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub tool_call_id: Option<String>,
 }
 
 #[cfg(test)]
@@ -1309,6 +1400,7 @@ mod tests {
             id: "call_0".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
         };
         let messages = vec![
             ChatMessage::user("Find test"),
@@ -1339,6 +1431,7 @@ mod tests {
             id: "call_0".to_string(),
             name: "http".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
         let messages = vec![
             ChatMessage::user("Fetch URL"),
@@ -1404,11 +1497,13 @@ mod tests {
             id: "call_a".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "data"}),
+            reasoning: None,
         };
         let tc2 = ToolCall {
             id: "call_b".to_string(),
             name: "write".to_string(),
             arguments: serde_json::json!({"path": "out.txt"}),
+            reasoning: None,
         };
         let messages = vec![
             ChatMessage::user("Find and save"),
@@ -1620,4 +1715,100 @@ mod tests {
         let merged = thread.drain_pending_messages().unwrap();
         assert_eq!(merged, "failed batch\nnew msg");
     }
+
+    #[test]
+    fn test_record_tool_result_for_by_id() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        // Record result for second tool by ID
+        turn.record_tool_result_for("id_b", serde_json::json!("result_b"));
+        assert!(turn.tool_calls[0].result.is_none());
+        assert_eq!(
+            turn.tool_calls[1].result.as_ref().unwrap(),
+            &serde_json::json!("result_b")
+        );
+    }
+
+    #[test]
+    fn test_record_tool_error_for_by_id() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        turn.record_tool_error_for("id_a", "failed");
+        assert_eq!(turn.tool_calls[0].error.as_deref(), Some("failed"));
+        assert!(turn.tool_calls[1].error.is_none());
+    }
+
+    #[test]
+    fn test_record_tool_result_for_fallback_to_pending() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        // First tool already has a result
+        turn.tool_calls[0].result = Some(serde_json::json!("done"));
+
+        // Unknown ID should fall back to first pending (tool_b)
+        turn.record_tool_result_for("unknown_id", serde_json::json!("fallback"));
+        assert_eq!(
+            turn.tool_calls[0].result.as_ref().unwrap(),
+            &serde_json::json!("done")
+        );
+        assert_eq!(
+            turn.tool_calls[1].result.as_ref().unwrap(),
+            &serde_json::json!("fallback")
+        );
+    }
+
+    #[test]
+    fn test_record_tool_result_for_no_pending_is_noop() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.tool_calls[0].result = Some(serde_json::json!("done"));
+
+        // No pending calls, unknown ID — should be a no-op
+        turn.record_tool_result_for("unknown_id", serde_json::json!("lost"));
+        assert_eq!(
+            turn.tool_calls[0].result.as_ref().unwrap(),
+            &serde_json::json!("done")
+        );
+    }
 }

src/agent/submission.rs

@@ -92,6 +92,17 @@ impl SubmissionParser {
                 args: vec![],
             };
         }
+        if lower == "/reasoning" || lower.starts_with("/reasoning ") {
+            let args: Vec<String> = trimmed
+                .split_whitespace()
+                .skip(1)
+                .map(|s| s.to_string())
+                .collect();
+            return Submission::SystemCommand {
+                command: "reasoning".to_string(),
+                args,
+            };
+        }
         if lower == "/restart" {
             tracing::debug!("[SubmissionParser::parse] Recognized /restart command");
             return Submission::SystemCommand {

src/agent/thread_ops.rs

@@ -513,10 +513,10 @@ impl Agent {
                 };
 
                 thread.complete_turn(&response);
-                let (turn_number, tool_calls) = thread
+                let (turn_number, tool_calls, narrative) = thread
                     .turns
                     .last()
-                    .map(|t| (t.turn_number, t.tool_calls.clone()))
+                    .map(|t| (t.turn_number, t.tool_calls.clone(), t.narrative.clone()))
                     .unwrap_or_default();
                 let _ = self
                     .channels
@@ -534,6 +534,7 @@ impl Agent {
                     &message.user_id,
                     turn_number,
                     &tool_calls,
+                    narrative.as_deref(),
                 )
                 .await;
                 self.persist_assistant_response(
@@ -725,7 +726,9 @@ impl Agent {
     ///
     /// Stored between the user and assistant messages so that
     /// `build_turns_from_db_messages` can reconstruct the tool call history.
-    /// Content is a JSON array of tool call summaries.
+    /// Content is a JSON object: `{ "calls": [...], "narrative": "..." }`.
+    /// The `calls` array contains tool call summaries with optional `rationale`
+    /// and `tool_call_id` fields. Legacy rows may be plain JSON arrays.
     pub(super) async fn persist_tool_calls(
         &self,
         thread_id: Uuid,
@@ -733,6 +736,7 @@ impl Agent {
         user_id: &str,
         turn_number: usize,
         tool_calls: &[crate::agent::session::TurnToolCall],
+        narrative: Option<&str>,
     ) {
         if tool_calls.is_empty() {
             return;
@@ -767,11 +771,30 @@ impl Agent {
                 if let Some(ref error) = tc.error {
                     obj["error"] = serde_json::Value::String(truncate_preview(error, 200));
                 }
+                if let Some(ref rationale) = tc.rationale {
+                    obj["rationale"] = serde_json::Value::String(truncate_preview(rationale, 500));
+                }
+                if let Some(ref tool_call_id) = tc.tool_call_id {
+                    obj["tool_call_id"] =
+                        serde_json::Value::String(truncate_preview(tool_call_id, 128));
+                }
                 obj
             })
             .collect();
 
-        let content = match serde_json::to_string(&summaries) {
+        // Wrap in an object with optional narrative so it can be reconstructed.
+        // safety: no byte-index slicing here; comment describes JSON shape
+        let wrapper = if let Some(n) = narrative {
+            serde_json::json!({
+                "narrative": truncate_preview(n, 1000),
+                "calls": summaries,
+            })
+        } else {
+            serde_json::json!({
+                "calls": summaries,
+            })
+        };
+        let content = match serde_json::to_string(&wrapper) {
             Ok(c) => c,
             Err(e) => {
                 tracing::warn!("Failed to serialize tool calls: {}", e);
@@ -1104,9 +1127,12 @@ impl Agent {
                     && let Some(turn) = thread.last_turn_mut()
                 {
                     if is_tool_error {
-                        turn.record_tool_error(result_content.clone());
+                        turn.record_tool_error_for(&pending.tool_call_id, result_content.clone());
                     } else {
-                        turn.record_tool_result(serde_json::json!(result_content));
+                        turn.record_tool_result_for(
+                            &pending.tool_call_id,
+                            serde_json::json!(result_content),
+                        );
                     }
                 }
             }
@@ -1358,9 +1384,12 @@ impl Agent {
                         && let Some(turn) = thread.last_turn_mut()
                     {
                         if is_deferred_error {
-                            turn.record_tool_error(deferred_content.clone());
+                            turn.record_tool_error_for(&tc.id, deferred_content.clone());
                         } else {
-                            turn.record_tool_result(serde_json::json!(deferred_content));
+                            turn.record_tool_result_for(
+                                &tc.id,
+                                serde_json::json!(deferred_content),
+                            );
                         }
                     }
                 }
@@ -1459,10 +1488,10 @@ impl Agent {
                     let (response, suggestions) =
                         crate::agent::dispatcher::extract_suggestions(&response);
                     thread.complete_turn(&response);
-                    let (turn_number, tool_calls) = thread
+                    let (turn_number, tool_calls, narrative) = thread
                         .turns
                         .last()
-                        .map(|t| (t.turn_number, t.tool_calls.clone()))
+                        .map(|t| (t.turn_number, t.tool_calls.clone(), t.narrative.clone()))
                         .unwrap_or_default();
                     // User message already persisted at turn start; save tool calls then assistant response
                     self.persist_tool_calls(
@@ -1471,6 +1500,7 @@ impl Agent {
                         &message.user_id,
                         turn_number,
                         &tool_calls,
+                        narrative.as_deref(),
                     )
                     .await;
                     self.persist_assistant_response(
@@ -1816,7 +1846,20 @@ fn rebuild_chat_messages_from_db(
             "assistant" => result.push(ChatMessage::assistant(&msg.content)),
             "tool_calls" => {
                 // Try to parse the enriched JSON and rebuild tool messages.
-                if let Ok(calls) = serde_json::from_str::<Vec<serde_json::Value>>(&msg.content) {
+                // Supports two formats:
+                // - Old: plain JSON array of tool call summaries
+                // - New: wrapped object { "calls": [...], "narrative": "..." }
+                let calls: Vec<serde_json::Value> =
+                    match serde_json::from_str::<serde_json::Value>(&msg.content) {
+                        Ok(serde_json::Value::Array(arr)) => arr,
+                        Ok(serde_json::Value::Object(obj)) => obj
+                            .get("calls")
+                            .and_then(|v| v.as_array())
+                            .cloned()
+                            .unwrap_or_default(),
+                        _ => Vec::new(),
+                    };
+                {
                     if calls.is_empty() {
                         continue;
                     }
@@ -1839,6 +1882,10 @@ fn rebuild_chat_messages_from_db(
                                     .get("parameters")
                                     .cloned()
                                     .unwrap_or(serde_json::json!({})),
+                                reasoning: c
+                                    .get("rationale")
+                                    .and_then(|v| v.as_str())
+                                    .map(String::from),
                             })
                             .collect();
 

src/channels/channel.rs

@@ -265,6 +265,15 @@ impl OutgoingResponse {
     }
 }
 
+/// A single tool decision within a reasoning update.
+#[derive(Debug, Clone)]
+pub struct ToolDecision {
+    /// Tool name.
+    pub tool_name: String,
+    /// Agent's reasoning for choosing this tool.
+    pub rationale: String,
+}
+
 /// Status update types for showing agent activity.
 #[derive(Debug, Clone)]
 pub enum StatusUpdate {
@@ -333,6 +342,13 @@ pub enum StatusUpdate {
     },
     /// Suggested follow-up messages for the user.
     Suggestions { suggestions: Vec<String> },
+    /// Agent reasoning update (why it chose specific tools).
+    ReasoningUpdate {
+        /// Human-readable summary of the agent's decision.
+        narrative: String,
+        /// Per-tool decisions.
+        decisions: Vec<ToolDecision>,
+    },
     /// Per-turn token usage and cost summary (shown as subtle metadata).
     TurnCost {
         input_tokens: u64,

src/channels/mod.rs

@@ -39,7 +39,7 @@ mod webhook_server;
 
 pub use channel::{
     AttachmentKind, Channel, ChannelSecretUpdater, IncomingAttachment, IncomingMessage,
-    MessageStream, OutgoingResponse, StatusUpdate, routing_target_from_metadata,
+    MessageStream, OutgoingResponse, StatusUpdate, ToolDecision, routing_target_from_metadata,
 };
 pub use http::{HttpChannel, HttpChannelState};
 pub use manager::ChannelManager;

src/channels/repl.rs

@@ -75,6 +75,7 @@ const SLASH_COMMANDS: &[&str] = &[
     "/suggest",
     "/thread",
     "/resume",
+    "/reasoning",
 ];
 
 /// Rustyline helper for slash-command tab completion.
@@ -430,6 +431,18 @@ impl ReplChannel {
             let _ = execute!(stderr, terminal::Clear(terminal::ClearType::FromCursorDown));
         }
     }
+
+    async fn finish_single_message_turn(&self) {
+        if self.single_message.is_none() {
+            return;
+        }
+
+        let tx = self.msg_tx.lock().ok().and_then(|mut guard| guard.take());
+        if let Some(tx) = tx {
+            let msg = IncomingMessage::new("repl", &self.user_id, "/quit");
+            let _ = tx.send(msg).await;
+        }
+    }
 }
 
 impl Default for ReplChannel {
@@ -479,7 +492,9 @@ impl Channel for ReplChannel {
 
     async fn start(&self) -> Result<MessageStream, ChannelError> {
         let (tx, rx) = mpsc::channel(32);
-        // Store tx so send_status can inject approval responses directly
+        // Approval prompts inject responses back through this sender.
+        // In single-message mode we keep it until the turn finishes, then
+        // drop it after enqueuing /quit so the receiver stream can close.
         if let Ok(mut guard) = self.msg_tx.lock() {
             *guard = Some(tx.clone());
         }
@@ -495,11 +510,10 @@ impl Channel for ReplChannel {
 
             // Single message mode: send it and return
             if let Some(msg) = single_message {
-                let incoming = IncomingMessage::new("repl", &user_id, &msg).with_timezone(&sys_tz);
+                let incoming = IncomingMessage::new("repl", &user_id, &msg)
+                    .with_metadata(serde_json::json!({ "single_message_mode": true }))
+                    .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", &user_id, "/quit"));
                 return;
             }
 
@@ -662,6 +676,7 @@ impl Channel for ReplChannel {
             println!();
             println!();
             self.stdin_locked.store(false, Ordering::Relaxed);
+            self.finish_single_message_turn().await;
             return Ok(());
         }
 
@@ -680,6 +695,7 @@ impl Channel for ReplChannel {
         println!();
         // Unlock stdin so readline can resume
         self.stdin_locked.store(false, Ordering::Relaxed);
+        self.finish_single_message_turn().await;
         Ok(())
     }
 
@@ -779,6 +795,7 @@ impl Channel for ReplChannel {
                 let msg_tx = Arc::clone(&self.msg_tx);
                 let user_id = self.user_id.clone();
                 let lock_flag = Arc::clone(&self.stdin_locked);
+                let single_message_mode = self.single_message.is_some();
                 tokio::task::spawn_blocking(move || {
                     let action = run_approval_selector(allow_always).unwrap_or("n");
                     // Unlock stdin so readline can resume after approval
@@ -787,7 +804,12 @@ impl Channel for ReplChannel {
                         return;
                     };
                     if let Some(tx) = guard.as_ref() {
-                        let msg = IncomingMessage::new("repl", &user_id, action);
+                        let msg = if single_message_mode {
+                            IncomingMessage::new("repl", &user_id, action)
+                                .with_metadata(serde_json::json!({ "single_message_mode": true }))
+                        } else {
+                            IncomingMessage::new("repl", &user_id, action)
+                        };
                         let _ = tx.blocking_send(msg);
                     }
                 });
@@ -841,6 +863,19 @@ impl Channel for ReplChannel {
             StatusUpdate::Suggestions { .. } => {
                 // Suggestions are only rendered by the web gateway
             }
+            StatusUpdate::ReasoningUpdate {
+                narrative,
+                decisions,
+            } => {
+                if !narrative.is_empty() {
+                    let display = truncate_for_preview(&narrative, CLI_STATUS_MAX);
+                    eprintln!("  \x1b[94m\u{25B6} {display}\x1b[0m");
+                }
+                for d in &decisions {
+                    let display = truncate_for_preview(&d.rationale, CLI_STATUS_MAX);
+                    eprintln!("    \x1b[90m\u{2192} {}: {display}\x1b[0m", d.tool_name);
+                }
+            }
             StatusUpdate::TurnCost { .. } => {
                 // Cost display is handled by the TUI channel
             }
@@ -875,6 +910,7 @@ impl Channel for ReplChannel {
 #[cfg(test)]
 mod tests {
     use futures::StreamExt;
+    use tokio::time::{Duration, timeout};
 
     use super::*;
 
@@ -883,16 +919,36 @@ mod tests {
         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");
+        let first = timeout(Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for first message")
+            .expect("first message missing");
         assert_eq!(first.channel, "repl");
         assert_eq!(first.content, "hi");
 
-        let second = stream.next().await.expect("quit message missing");
+        assert!(
+            timeout(Duration::from_millis(100), stream.next())
+                .await
+                .is_err(),
+            "single-message mode should wait for the turn to finish before quitting"
+        );
+
+        repl.respond(&first, OutgoingResponse::text("done"))
+            .await
+            .expect("respond should succeed");
+
+        let second = timeout(Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for quit message")
+            .expect("quit message missing");
         assert_eq!(second.channel, "repl");
         assert_eq!(second.content, "/quit");
 
         assert!(
-            stream.next().await.is_none(),
+            timeout(Duration::from_secs(1), stream.next())
+                .await
+                .expect("timed out waiting for stream to close")
+                .is_none(),
             "stream should end after /quit"
         );
     }

src/channels/wasm/wrapper.rs

@@ -3061,6 +3061,20 @@ fn status_to_wit(
         },
         // Suggestions and turn cost are web-gateway-only; skip for WASM channels
         StatusUpdate::Suggestions { .. } | StatusUpdate::TurnCost { .. } => return None,
+        StatusUpdate::ReasoningUpdate {
+            narrative,
+            decisions,
+        } => {
+            let mut msg = narrative.clone();
+            for d in decisions {
+                msg.push_str(&format!("\n  → {}: {}", d.tool_name, d.rationale));
+            }
+            wit_channel::StatusUpdate {
+                status: wit_channel::StatusType::Status,
+                message: msg,
+                metadata_json,
+            }
+        }
     })
 }
 

src/channels/web/handlers/chat.rs

@@ -398,8 +398,10 @@ pub async fn chat_history_handler(
                                 truncate_preview(&s, 500)
                             }),
                             error: tc.error.clone(),
+                            rationale: tc.rationale.clone(),
                         })
                         .collect(),
+                    narrative: t.narrative.clone(),
                 })
                 .collect();
 

src/channels/web/mod.rs

@@ -489,6 +489,20 @@ impl Channel for GatewayChannel {
             },
             StatusUpdate::Suggestions { suggestions } => AppEvent::Suggestions {
                 suggestions,
+                thread_id: thread_id.clone(),
+            },
+            StatusUpdate::ReasoningUpdate {
+                narrative,
+                decisions,
+            } => AppEvent::ReasoningUpdate {
+                narrative,
+                decisions: decisions
+                    .into_iter()
+                    .map(|d| crate::channels::web::types::ToolDecisionDto {
+                        tool_name: d.tool_name,
+                        rationale: d.rationale,
+                    })
+                    .collect(),
                 thread_id,
             },
             StatusUpdate::TurnCost {

src/channels/web/openai_compat.rs

@@ -231,6 +231,7 @@ pub fn convert_messages(messages: &[OpenAiMessage]) -> Result<Vec<ChatMessage>,
                                 name: tc.function.name.clone(),
                                 arguments: serde_json::from_str(&tc.function.arguments)
                                     .unwrap_or(serde_json::Value::Object(Default::default())),
+                                reasoning: None,
                             })
                             .collect();
                         Ok(ChatMessage::assistant_with_tool_calls(
@@ -954,6 +955,7 @@ mod tests {
             id: "call_abc".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "rust"}),
+            reasoning: None,
         }];
 
         let converted = convert_tool_calls_to_openai(&calls);

src/channels/web/server.rs

@@ -1725,8 +1725,10 @@ async fn chat_history_handler(
                             truncate_preview(&s, 500)
                         }),
                         error: tc.error.clone(),
+                        rationale: tc.rationale.clone(),
                     })
                     .collect(),
+                narrative: t.narrative.clone(),
             })
             .collect();
 

src/channels/web/types.rs

@@ -63,6 +63,9 @@ pub struct TurnInfo {
     pub started_at: String,
     pub completed_at: Option<String>,
     pub tool_calls: Vec<ToolCallInfo>,
+    /// Agent's reasoning narrative for this turn.
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub narrative: Option<String>,
 }
 
 #[derive(Debug, Serialize)]
@@ -74,6 +77,9 @@ pub struct ToolCallInfo {
     pub result_preview: Option<String>,
     #[serde(skip_serializing_if = "Option::is_none")]
     pub error: Option<String>,
+    /// Agent's reasoning for choosing this tool.
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub rationale: Option<String>,
 }
 
 #[derive(Debug, Serialize)]
@@ -116,7 +122,7 @@ pub struct ApprovalRequest {
 
 // --- App Event (re-exported from ironclaw_common) ---
 
-pub use ironclaw_common::AppEvent;
+pub use ironclaw_common::{AppEvent, ToolDecisionDto};
 
 // --- Memory ---
 

src/channels/web/util.rs

@@ -4,6 +4,21 @@ use crate::channels::web::types::{ToolCallInfo, TurnInfo};
 
 pub use ironclaw_common::truncate_preview;
 
+/// Parse tool call summary JSON objects into `ToolCallInfo` structs.
+fn parse_tool_call_infos(calls: &[serde_json::Value]) -> Vec<ToolCallInfo> {
+    calls
+        .iter()
+        .map(|c| ToolCallInfo {
+            name: c["name"].as_str().unwrap_or("unknown").to_string(),
+            has_result: c.get("result_preview").is_some_and(|v| !v.is_null()),
+            has_error: c.get("error").is_some_and(|v| !v.is_null()),
+            result_preview: c["result_preview"].as_str().map(String::from),
+            error: c["error"].as_str().map(String::from),
+            rationale: c["rationale"].as_str().map(String::from),
+        })
+        .collect()
+}
+
 /// Build TurnInfo pairs from flat DB messages (user/tool_calls/assistant triples).
 ///
 /// Handles three message patterns:
@@ -27,6 +42,7 @@ pub fn build_turns_from_db_messages(
                 started_at: msg.created_at.to_rfc3339(),
                 completed_at: None,
                 tool_calls: Vec::new(),
+                narrative: None,
             };
 
             // Check if next message is a tool_calls record
@@ -34,18 +50,28 @@ pub fn build_turns_from_db_messages(
                 && next.role == "tool_calls"
             {
                 let tc_msg = iter.next().expect("peeked");
-                match serde_json::from_str::<Vec<serde_json::Value>>(&tc_msg.content) {
-                    Ok(calls) => {
-                        turn.tool_calls = calls
-                            .iter()
-                            .map(|c| ToolCallInfo {
-                                name: c["name"].as_str().unwrap_or("unknown").to_string(),
-                                has_result: c.get("result_preview").is_some(),
-                                has_error: c.get("error").is_some(),
-                                result_preview: c["result_preview"].as_str().map(String::from),
-                                error: c["error"].as_str().map(String::from),
-                            })
-                            .collect();
+                // Parse tool_calls JSON — supports two formats:
+                // safety: no byte-index slicing; comment describes JSON shape
+                match serde_json::from_str::<serde_json::Value>(&tc_msg.content) {
+                    Ok(serde_json::Value::Array(calls)) => {
+                        // Old format: plain array
+                        turn.tool_calls = parse_tool_call_infos(&calls);
+                    }
+                    Ok(serde_json::Value::Object(obj)) => {
+                        // New wrapped format with narrative
+                        turn.narrative = obj
+                            .get("narrative")
+                            .and_then(|v| v.as_str())
+                            .map(String::from);
+                        if let Some(serde_json::Value::Array(calls)) = obj.get("calls") {
+                            turn.tool_calls = parse_tool_call_infos(calls);
+                        }
+                    }
+                    Ok(_) => {
+                        tracing::warn!(
+                            message_id = %tc_msg.id,
+                            "Unexpected tool_calls JSON shape in DB, skipping"
+                        );
                     }
                     Err(e) => {
                         tracing::warn!(
@@ -83,6 +109,7 @@ pub fn build_turns_from_db_messages(
                 started_at: msg.created_at.to_rfc3339(),
                 completed_at: Some(msg.created_at.to_rfc3339()),
                 tool_calls: Vec::new(),
+                narrative: None,
             });
             turn_number += 1;
         }
@@ -201,4 +228,52 @@ mod tests {
         assert!(turns[0].tool_calls.is_empty());
         assert_eq!(turns[0].state, "Completed");
     }
+
+    #[test]
+    fn test_build_turns_with_wrapped_tool_calls_format() {
+        let tc_json = serde_json::json!({
+            "narrative": "Searching memory for context before proceeding.",
+            "calls": [
+                {"name": "memory_search", "result_preview": "found 3 items", "rationale": "consult prior context"},
+                {"name": "shell", "error": "permission denied"}
+            ]
+        });
+        let messages = vec![
+            make_msg("user", "Find info", 0),
+            make_msg("tool_calls", &tc_json.to_string(), 500),
+            make_msg("assistant", "Here's what I found", 1000),
+        ];
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 1);
+        assert_eq!(
+            turns[0].narrative.as_deref(),
+            Some("Searching memory for context before proceeding.")
+        );
+        assert_eq!(turns[0].tool_calls.len(), 2);
+        assert_eq!(turns[0].tool_calls[0].name, "memory_search");
+        assert_eq!(
+            turns[0].tool_calls[0].rationale.as_deref(),
+            Some("consult prior context")
+        );
+        assert!(turns[0].tool_calls[0].has_result);
+        assert_eq!(turns[0].tool_calls[1].name, "shell");
+        assert!(turns[0].tool_calls[1].has_error);
+        assert_eq!(turns[0].response.as_deref(), Some("Here's what I found"));
+    }
+
+    #[test]
+    fn test_build_turns_wrapped_format_without_narrative() {
+        let tc_json = serde_json::json!({
+            "calls": [{"name": "echo", "result_preview": "hello"}]
+        });
+        let messages = vec![
+            make_msg("user", "Say hi", 0),
+            make_msg("tool_calls", &tc_json.to_string(), 500),
+            make_msg("assistant", "Done", 1000),
+        ];
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 1);
+        assert!(turns[0].narrative.is_none());
+        assert_eq!(turns[0].tool_calls.len(), 1);
+    }
 }

src/llm/anthropic_oauth.rs

@@ -575,6 +575,7 @@ fn extract_response_content(response: &AnthropicResponse) -> (Option<String>, Ve
                     id: id.clone(),
                     name: name.clone(),
                     arguments: input.clone(),
+                    reasoning: None,
                 });
             }
         }
@@ -623,6 +624,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
         }];
         let messages = vec![
             ChatMessage::user("Search for test"),

src/llm/bedrock.rs

@@ -522,6 +522,7 @@ fn extract_content_blocks(
                     id: tu.tool_use_id().to_string(),
                     name: tu.name().to_string(),
                     arguments: document_to_json(tu.input()),
+                    reasoning: None,
                 });
             }
             // Ignore reasoning, citations, images, etc.
@@ -759,11 +760,13 @@ mod tests {
             id: "call_1".to_string(),
             name: "echo".to_string(),
             arguments: serde_json::json!({"text": "hi"}),
+            reasoning: None,
         };
         let tc2 = crate::llm::provider::ToolCall {
             id: "call_2".to_string(),
             name: "time".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
 
         let messages = vec![
@@ -802,6 +805,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "test"}),
+            reasoning: None,
         };
 
         let messages = vec![
@@ -825,6 +829,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "echo".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
 
         let messages = vec![
@@ -989,11 +994,13 @@ mod tests {
             id: "call_abc".to_string(),
             name: "get_weather".to_string(),
             arguments: serde_json::json!({"city": "NYC"}),
+            reasoning: None,
         };
         let tc2 = crate::llm::provider::ToolCall {
             id: "call_def".to_string(),
             name: "get_time".to_string(),
             arguments: serde_json::json!({"tz": "EST"}),
+            reasoning: None,
         };
 
         let messages = vec![

src/llm/codex_chatgpt.rs

@@ -732,6 +732,7 @@ impl LlmProvider for CodexChatGptProvider {
                     id: tc.call_id,
                     name: tc.name,
                     arguments: args,
+                    reasoning: None,
                 }
             })
             .collect();
@@ -825,6 +826,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "search".to_string(),
             arguments: json!({"query": "rust"}),
+            reasoning: None,
         };
         let msg = ChatMessage::assistant_with_tool_calls(Some("thinking...".into()), vec![tc]);
         let items = CodexChatGptProvider::message_to_input_items(&msg);

src/llm/gemini_oauth.rs

@@ -1898,6 +1898,7 @@ impl GeminiOauthProvider {
                         id,
                         name,
                         arguments: args,
+                        reasoning: None,
                     });
                 }
             }

src/llm/github_copilot.rs

@@ -596,6 +596,7 @@ fn extract_choice_content(choice: &OpenAiChoice) -> (Option<String>, Vec<ToolCal
                     name: tc.function.name.clone(),
                     arguments: serde_json::from_str(&tc.function.arguments)
                         .unwrap_or(serde_json::Value::Object(serde_json::Map::new())),
+                    reasoning: None,
                 })
                 .collect()
         })
@@ -628,6 +629,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
         }];
         let messages = vec![
             ChatMessage::user("Search"),

src/llm/nearai_chat.rs

@@ -587,6 +587,7 @@ impl LlmProvider for NearAiChatProvider {
                     id: tc.id,
                     name: tc.function.name,
                     arguments,
+                    reasoning: None,
                 }
             })
             .collect();
@@ -1180,11 +1181,13 @@ mod tests {
                 id: "call_1".to_string(),
                 name: "list_issues".to_string(),
                 arguments: serde_json::json!({"owner": "foo", "repo": "bar"}),
+                reasoning: None,
             },
             ToolCall {
                 id: "call_2".to_string(),
                 name: "search".to_string(),
                 arguments: serde_json::json!({"query": "test"}),
+                reasoning: None,
             },
         ];
 
@@ -1217,6 +1220,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "test".to_string(),
             arguments: serde_json::json!({"key": "value"}),
+            reasoning: None,
         };
         let msg = ChatMessage::assistant_with_tool_calls(None, vec![tc]);
         let chat_msg: ChatCompletionMessage = msg.into();
@@ -1460,6 +1464,7 @@ mod tests {
                     id: tc.id,
                     name: tc.function.name,
                     arguments,
+                    reasoning: None,
                 }
             })
             .collect();
@@ -1509,6 +1514,7 @@ mod tests {
                     id: tc.id,
                     name: tc.function.name,
                     arguments,
+                    reasoning: None,
                 }
             })
             .collect();
@@ -2131,6 +2137,7 @@ mod tests {
                 id: "call_1".to_string(),
                 name: "test".to_string(),
                 arguments: serde_json::json!({}),
+                reasoning: None,
             }],
         );
         let chat_msg: ChatCompletionMessage = msg.into();

src/llm/openai_codex_provider.rs

@@ -625,6 +625,7 @@ fn parse_sse_response(body: &str) -> Result<ParsedResponse, LlmError> {
                                 id: state.call_id,
                                 name: state.name,
                                 arguments,
+                                reasoning: None,
                             });
                         } else {
                             // Fallback: extract directly from the item
@@ -650,6 +651,7 @@ fn parse_sse_response(body: &str) -> Result<ParsedResponse, LlmError> {
                                 id: call_id,
                                 name,
                                 arguments,
+                                reasoning: None,
                             });
                         }
                     }
@@ -727,6 +729,7 @@ fn parse_sse_response(body: &str) -> Result<ParsedResponse, LlmError> {
                 id: state.call_id,
                 name: state.name,
                 arguments,
+                reasoning: None,
             });
         }
     }
@@ -822,11 +825,13 @@ mod tests {
                 id: "call_1".to_string(),
                 name: "search".to_string(),
                 arguments: serde_json::json!({"query": "test"}),
+                reasoning: None,
             },
             ToolCall {
                 id: "call_2".to_string(),
                 name: "read".to_string(),
                 arguments: serde_json::json!({"path": "/tmp"}),
+                reasoning: None,
             },
         ];
         let msg =

src/llm/provider.rs

@@ -231,6 +231,10 @@ pub struct ToolCall {
     pub id: String,
     pub name: String,
     pub arguments: serde_json::Value,
+    /// Optional reasoning for why this tool was chosen — supplied by the provider
+    /// or derived from the shared response content as a fallback.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub reasoning: Option<String>,
 }
 
 /// Generate a tool-call ID that satisfies all providers.
@@ -637,6 +641,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "echo".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
         let mut messages = vec![
             ChatMessage::user("hello"),
@@ -680,6 +685,7 @@ mod tests {
             id: "call_1".to_string(),
             name: "echo".to_string(),
             arguments: serde_json::json!({}),
+            reasoning: None,
         };
         let mut messages = vec![
             ChatMessage::user("test"),
@@ -705,11 +711,13 @@ mod tests {
             id: "call_sel_1".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
         };
         let tc2 = ToolCall {
             id: "call_sel_2".to_string(),
             name: "http".to_string(),
             arguments: serde_json::json!({"url": "https://example.com"}),
+            reasoning: None,
         };
         let mut messages = vec![
             ChatMessage::system("You are a helpful assistant."),

src/llm/reasoning.rs

@@ -525,17 +525,35 @@ impl Reasoning {
 
         let response = self.llm.complete_with_tools(request).await?;
 
-        let reasoning = response.content.unwrap_or_default();
+        let shared_reasoning = response
+            .content
+            .map(|c| {
+                let pre_truncated = truncate_at_tool_tags(&c);
+                clean_response(&pre_truncated)
+            })
+            .unwrap_or_default();
 
         let selections: Vec<ToolSelection> = response
             .tool_calls
             .into_iter()
-            .map(|tool_call| ToolSelection {
-                tool_name: tool_call.name,
-                parameters: tool_call.arguments,
-                reasoning: reasoning.clone(),
-                alternatives: vec![],
-                tool_call_id: tool_call.id,
+            .map(|tool_call| {
+                // Prefer per-tool reasoning if the provider supplied it,
+                // otherwise fall back to the shared response content.
+                let rationale = tool_call
+                    .reasoning
+                    .map(|r| {
+                        let pre_truncated = truncate_at_tool_tags(&r);
+                        clean_response(&pre_truncated)
+                    })
+                    .filter(|r| !r.trim().is_empty())
+                    .unwrap_or_else(|| shared_reasoning.clone());
+                ToolSelection {
+                    tool_name: tool_call.name,
+                    parameters: tool_call.arguments,
+                    reasoning: rationale,
+                    alternatives: vec![],
+                    tool_call_id: tool_call.id,
+                }
             })
             .collect();
 
@@ -664,13 +682,36 @@ Respond in JSON format:
 
             // If there were tool calls, return them for execution
             if !response.tool_calls.is_empty() {
+                let narrative = response.content.map(|c| {
+                    let pre_truncated = truncate_at_tool_tags(&c);
+                    clean_response(&pre_truncated)
+                });
+                // Populate per-tool reasoning from the shared narrative when the
+                // provider did not supply per-tool rationale.
+                let tool_calls: Vec<ToolCall> = response
+                    .tool_calls
+                    .into_iter()
+                    .map(|mut tc| {
+                        if tc.reasoning.as_ref().is_none_or(|r| r.trim().is_empty()) {
+                            tc.reasoning = narrative.as_ref().filter(|n| !n.is_empty()).cloned();
+                        } else {
+                            // Clean provider-supplied per-tool reasoning the same way
+                            // we clean the shared narrative (strip thinking/tool tags).
+                            tc.reasoning = tc
+                                .reasoning
+                                .map(|r| {
+                                    let pre_truncated = truncate_at_tool_tags(&r);
+                                    clean_response(&pre_truncated)
+                                })
+                                .filter(|r| !r.trim().is_empty());
+                        }
+                        tc
+                    })
+                    .collect();
                 return Ok(RespondOutput {
                     result: RespondResult::ToolCalls {
-                        tool_calls: response.tool_calls,
-                        content: response.content.map(|c| {
-                            let pre_truncated = truncate_at_tool_tags(&c);
-                            clean_response(&pre_truncated)
-                        }),
+                        tool_calls,
+                        content: narrative,
                     },
                     usage,
                 });
@@ -1350,6 +1391,7 @@ fn recover_tool_calls_from_content(
                     ),
                     name: name.to_string(),
                     arguments,
+                    reasoning: None,
                 });
                 continue;
             }
@@ -1364,6 +1406,7 @@ fn recover_tool_calls_from_content(
                     ),
                     name: name.to_string(),
                     arguments: serde_json::Value::Object(Default::default()),
+                    reasoning: None,
                 });
             }
         }
@@ -1401,6 +1444,7 @@ fn recover_tool_calls_from_content(
                         ),
                         name: name.to_string(),
                         arguments,
+                        reasoning: None,
                     });
                     remaining = &args_start[bracket_end + 1..];
                     continue;
@@ -1412,6 +1456,7 @@ fn recover_tool_calls_from_content(
                 id: super::provider::generate_tool_call_id(calls.len(), RECOVERED_TOOL_CALL_SEED),
                 name: name.to_string(),
                 arguments: serde_json::Value::Object(Default::default()),
+                reasoning: None,
             });
             remaining = after_name;
         }
@@ -3145,4 +3190,32 @@ That's my plan."#;
             "Text <function_call>{}</function_call> middle "
         );
     }
+
+    /// Verify that reasoning normalization strips thinking tags and tool tags
+    /// from per-tool reasoning, matching the cleaning applied to shared reasoning.
+    #[test]
+    fn test_reasoning_normalization_strips_thinking_tags() {
+        let raw = "<thinking>Let me consider...</thinking>Search memory for prior context";
+        let pre_truncated = truncate_at_tool_tags(raw);
+        let cleaned = clean_response(&pre_truncated);
+        assert!(!cleaned.contains("<thinking>"));
+        assert!(cleaned.contains("Search memory"));
+    }
+
+    #[test]
+    fn test_reasoning_normalization_strips_tool_tags() {
+        let raw = "Calling search <tool_call>{\"name\": \"search\"}";
+        let pre_truncated = truncate_at_tool_tags(raw);
+        let cleaned = clean_response(&pre_truncated);
+        assert!(!cleaned.contains("<tool_call>"));
+        assert!(cleaned.contains("Calling search"));
+    }
+
+    #[test]
+    fn test_reasoning_normalization_empty_after_cleaning() {
+        let raw = "<thinking>internal only</thinking>";
+        let pre_truncated = truncate_at_tool_tags(raw);
+        let cleaned = clean_response(&pre_truncated);
+        assert!(cleaned.trim().is_empty());
+    }
 }

src/llm/rig_adapter.rs

@@ -490,6 +490,7 @@ fn extract_response(
                     id: tc.id.clone(),
                     name: tc.function.name.clone(),
                     arguments: tc.function.arguments.clone(),
+                    reasoning: None,
                 });
             }
             // Reasoning and Image variants are not mapped to IronClaw types
@@ -880,6 +881,7 @@ mod tests {
             id: "Xt7mK9pQ2".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "test"}),
+            reasoning: None,
         };
         let msg = ChatMessage::assistant_with_tool_calls(Some("thinking".to_string()), vec![tc]);
         let messages = vec![msg];
@@ -997,6 +999,7 @@ mod tests {
             id: "".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "test"}),
+            reasoning: None,
         };
         let messages = vec![ChatMessage::assistant_with_tool_calls(None, vec![tc])];
         let (_preamble, history) = convert_messages(&messages);
@@ -1028,6 +1031,7 @@ mod tests {
             id: "   ".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "test"}),
+            reasoning: None,
         };
         let messages = vec![ChatMessage::assistant_with_tool_calls(None, vec![tc])];
         let (_preamble, history) = convert_messages(&messages);
@@ -1061,6 +1065,7 @@ mod tests {
             id: "".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"query": "test"}),
+            reasoning: None,
         };
         let assistant_msg = ChatMessage::assistant_with_tool_calls(None, vec![tc]);
         let tool_result_msg = ChatMessage {
@@ -1380,11 +1385,13 @@ mod tests {
             id: "call_a".to_string(),
             name: "search".to_string(),
             arguments: serde_json::json!({"q": "rust"}),
+            reasoning: None,
         };
         let tc2 = IronToolCall {
             id: "call_b".to_string(),
             name: "fetch".to_string(),
             arguments: serde_json::json!({"url": "https://example.com"}),
+            reasoning: None,
         };
         let assistant = ChatMessage::assistant_with_tool_calls(None, vec![tc1, tc2]);
         let result_a = ChatMessage::tool_result("call_a", "search", "search results");

src/orchestrator/api.rs

@@ -14,6 +14,7 @@ use serde::{Deserialize, Serialize};
 use tokio::sync::{Mutex, broadcast};
 use uuid::Uuid;
 
+use crate::channels::web::types::ToolDecisionDto;
 use crate::db::Database;
 use crate::llm::{CompletionRequest, LlmProvider, ToolCompletionRequest};
 use crate::orchestrator::auth::{TokenStore, worker_auth_middleware};
@@ -344,6 +345,20 @@ async fn job_event_handler(
             // gain context/memory tracking capabilities.
             fallback_deliverable: payload.data.get("fallback_deliverable").cloned(),
         },
+        "reasoning" => {
+            let narrative = payload
+                .data
+                .get("narrative")
+                .and_then(|v| v.as_str())
+                .unwrap_or("")
+                .to_string();
+            let decisions = ToolDecisionDto::from_json_array(&payload.data["decisions"]);
+            AppEvent::JobReasoning {
+                job_id: job_id_str,
+                narrative,
+                decisions,
+            }
+        }
         _ => AppEvent::JobStatus {
             job_id: job_id_str,
             message: payload

src/tools/builtin/routine.rs

@@ -915,7 +915,7 @@ fn parse_routine_create_request(
 fn build_routine_trigger(trigger: &NormalizedTriggerRequest) -> Trigger {
     match trigger {
         NormalizedTriggerRequest::Cron { schedule, timezone } => Trigger::Cron {
-            schedule: schedule.clone(),
+            schedule: normalize_cron_expression(schedule),
             timezone: timezone.clone(),
         },
         NormalizedTriggerRequest::Manual => Trigger::Manual,
@@ -1836,6 +1836,20 @@ mod tests {
         assert_eq!(parsed.cooldown_secs, 30);
     }
 
+    #[test]
+    fn build_routine_trigger_normalizes_cron_schedule() {
+        let trigger = build_routine_trigger(&NormalizedTriggerRequest::Cron {
+            schedule: "0 0 9 * * MON-FRI".to_string(),
+            timezone: Some("UTC".to_string()),
+        });
+
+        assert!(matches!(
+            trigger,
+            Trigger::Cron { schedule, timezone }
+                if schedule == "0 0 9 * * MON-FRI *" && timezone.as_deref() == Some("UTC")
+        ));
+    }
+
     #[test]
     fn parses_grouped_message_event_with_tools() {
         let params = serde_json::json!({

src/worker/job.rs

@@ -18,6 +18,7 @@ use crate::agent::agentic_loop::{
 };
 use crate::agent::scheduler::WorkerMessage;
 use crate::agent::task::TaskOutput;
+use crate::channels::web::types::ToolDecisionDto;
 use crate::context::{ContextManager, JobState};
 use crate::db::Database;
 use crate::error::Error;
@@ -200,6 +201,19 @@ impl Worker {
                         .map(|s| s.to_string()),
                     fallback_deliverable: data.get("fallback_deliverable").cloned(),
                 }),
+                "reasoning" => {
+                    let narrative = data
+                        .get("narrative")
+                        .and_then(|v| v.as_str())
+                        .unwrap_or("")
+                        .to_string();
+                    let decisions = ToolDecisionDto::from_json_array(&data["decisions"]);
+                    Some(AppEvent::JobReasoning {
+                        job_id: job_id_str,
+                        narrative,
+                        decisions,
+                    })
+                }
                 _ => None,
             };
             if let Some(event) = event {
@@ -897,6 +911,11 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                         id: selection.tool_call_id.clone(),
                         name: selection.tool_name.clone(),
                         arguments: selection.parameters.clone(),
+                        reasoning: if action.reasoning.is_empty() {
+                            None
+                        } else {
+                            Some(action.reasoning.clone())
+                        },
                     }],
                 ));
 
@@ -1357,6 +1376,48 @@ impl<'a> LoopDelegate for JobDelegate<'a> {
             );
         }
 
+        // Emit reasoning event if any tool calls carry reasoning.
+        // Sanitize narrative and per-tool rationale through SafetyLayer
+        // (parity with ChatDelegate in dispatcher.rs).
+        let sanitized_narrative = content
+            .as_deref()
+            .filter(|c| !c.trim().is_empty())
+            .map(|c| {
+                self.worker
+                    .deps
+                    .safety
+                    .sanitize_tool_output("job_narrative", c)
+                    .content
+            })
+            .filter(|c| !c.trim().is_empty())
+            .unwrap_or_default();
+        let decisions: Vec<serde_json::Value> = tool_calls
+            .iter()
+            .filter_map(|tc| {
+                tc.reasoning.as_ref().map(|r| {
+                    let sanitized = self
+                        .worker
+                        .deps
+                        .safety
+                        .sanitize_tool_output("tool_rationale", r)
+                        .content;
+                    serde_json::json!({
+                        "tool_name": tc.name,
+                        "rationale": sanitized,
+                    })
+                })
+            })
+            .collect();
+        if !decisions.is_empty() {
+            self.worker.log_event(
+                "reasoning",
+                serde_json::json!({
+                    "narrative": sanitized_narrative,
+                    "decisions": decisions,
+                }),
+            );
+        }
+
         // Add assistant message with tool_calls (OpenAI protocol)
         reason_ctx
             .messages
@@ -1371,7 +1432,7 @@ impl<'a> LoopDelegate for JobDelegate<'a> {
             .map(|tc| ToolSelection {
                 tool_name: tc.name.clone(),
                 parameters: tc.arguments.clone(),
-                reasoning: String::new(),
+                reasoning: tc.reasoning.clone().unwrap_or_default(),
                 alternatives: vec![],
                 tool_call_id: tc.id.clone(),
             })
@@ -1424,6 +1485,11 @@ fn selections_to_tool_calls(selections: &[ToolSelection]) -> Vec<ToolCall> {
             id: s.tool_call_id.clone(),
             name: s.tool_name.clone(),
             arguments: s.parameters.clone(),
+            reasoning: if s.reasoning.is_empty() {
+                None
+            } else {
+                Some(s.reasoning.clone())
+            },
         })
         .collect()
 }

src/workspace/mod.rs

@@ -149,6 +149,7 @@ fn reject_if_injected(path: &str, content: &str) -> Result<(), WorkspaceError> {
 ///
 /// Allows Workspace to work with either a PostgreSQL `Repository` (the original
 /// path) or any `Database` trait implementation (e.g. libSQL backend).
+#[derive(Clone)]
 enum WorkspaceStorage {
     /// PostgreSQL-backed repository (uses connection pool directly).
     #[cfg(feature = "postgres")]
@@ -576,6 +577,60 @@ impl Workspace {
         self
     }
 
+    /// Clone the workspace configuration for a different primary user scope.
+    ///
+    /// This preserves search config, embeddings, shared read scopes, memory
+    /// layers, and privacy classifier while switching the primary read/write
+    /// scope to `user_id`.
+    pub fn scoped_to_user(&self, user_id: impl Into<String>) -> Self {
+        let user_id = user_id.into();
+
+        let mut memory_layers = self.memory_layers.clone();
+        for layer in &mut memory_layers {
+            if layer.sensitivity == crate::workspace::layer::LayerSensitivity::Private
+                && layer.scope == self.user_id
+            {
+                layer.scope = user_id.clone();
+            }
+        }
+
+        let mut read_user_ids = vec![user_id.clone()];
+        for scope in &self.read_user_ids {
+            if scope != &self.user_id && !read_user_ids.contains(scope) {
+                read_user_ids.push(scope.clone());
+            }
+        }
+        for scope in crate::workspace::layer::MemoryLayer::read_scopes(&memory_layers) {
+            if !read_user_ids.contains(&scope) {
+                read_user_ids.push(scope);
+            }
+        }
+
+        let preserve_flags = user_id == self.user_id;
+        Self {
+            user_id,
+            read_user_ids,
+            agent_id: self.agent_id,
+            storage: self.storage.clone(),
+            embeddings: self.embeddings.clone(),
+            bootstrap_pending: std::sync::atomic::AtomicBool::new(if preserve_flags {
+                self.bootstrap_pending
+                    .load(std::sync::atomic::Ordering::Acquire)
+            } else {
+                false
+            }),
+            bootstrap_completed: std::sync::atomic::AtomicBool::new(if preserve_flags {
+                self.bootstrap_completed
+                    .load(std::sync::atomic::Ordering::Acquire)
+            } else {
+                false
+            }),
+            search_defaults: self.search_defaults.clone(),
+            memory_layers,
+            privacy_classifier: self.privacy_classifier.clone(),
+        }
+    }
+
     /// Get the user ID (primary scope for writes).
     pub fn user_id(&self) -> &str {
         &self.user_id

src/workspace/repository.rs

@@ -15,6 +15,7 @@ use crate::workspace::document::{MemoryChunk, MemoryDocument, WorkspaceEntry};
 use crate::workspace::search::{RankedResult, SearchConfig, SearchResult, fuse_results};
 
 /// Database repository for workspace operations.
+#[derive(Clone)]
 pub struct Repository {
     pool: Pool,
 }

tests/e2e/scenarios/test_telegram_hot_activation.py

@@ -253,6 +253,6 @@ async def test_telegram_hot_activation_transitions_installed_to_active(page):
     assert await card.locator(SEL["ext_pairing_label"]).count() == 0
 
     assert captured_setup_payloads == [
-        {"secrets": {"telegram_bot_token": "123456789:ABCdefGhI"}},
-        {"secrets": {}},
+        {"secrets": {"telegram_bot_token": "123456789:ABCdefGhI"}, "fields": {}},
+        {"secrets": {}, "fields": {}},
     ]

tests/e2e_advanced_traces.rs

@@ -587,6 +587,7 @@ mod advanced {
     async fn mcp_extension_lifecycle() {
         use crate::support::mock_mcp_server::{MockToolResponse, start_mock_mcp_server};
         use ironclaw::extensions::{AuthHint, ExtensionKind, ExtensionSource, RegistryEntry};
+        const TEST_USER_ID: &str = "test-user";
 
         // 1. Start mock MCP server with pre-configured tool responses.
         let mock_server = start_mock_mcp_server(vec![
@@ -654,14 +655,14 @@ mod advanced {
         ext_mgr
             .secrets()
             .create(
-                "default",
+                TEST_USER_ID,
                 ironclaw::secrets::CreateSecretParams::new(secret_name, "mock-access-token")
                     .with_provider("mcp:mock-notion".to_string()),
             )
             .await
             .expect("failed to inject test token");
 
-        let activate_result = ext_mgr.activate("mock-notion", "default").await;
+        let activate_result = ext_mgr.activate("mock-notion", TEST_USER_ID).await;
         assert!(
             activate_result.is_ok(),
             "activation failed: {:?}",

tests/e2e_builtin_tool_coverage.rs

@@ -439,7 +439,7 @@ mod tests {
 
         match &routine.trigger {
             Trigger::Cron { schedule, timezone } => {
-                assert_eq!(schedule, "0 0 9 * * MON-FRI");
+                assert_eq!(schedule, "0 0 9 * * MON-FRI *");
                 assert_eq!(timezone.as_deref(), Some("UTC"));
             }
             other => panic!("expected cron trigger, got {other:?}"),

tests/e2e_workspace_coverage.rs

@@ -12,6 +12,7 @@ mod tests {
 
     use crate::support::test_rig::TestRigBuilder;
     use crate::support::trace_llm::LlmTrace;
+    use ironclaw::workspace::Workspace;
 
     // -----------------------------------------------------------------------
     // Test 1: write_chunk_search
@@ -268,6 +269,7 @@ mod tests {
 
     #[tokio::test]
     async fn identity_in_system_prompt() {
+        const TEST_USER_ID: &str = "test-user";
         let trace = LlmTrace::from_file(concat!(
             env!("CARGO_MANIFEST_DIR"),
             "/tests/fixtures/llm_traces/workspace/identity_prompt.json"
@@ -280,7 +282,7 @@ mod tests {
             .await;
 
         // Seed an IDENTITY.md so the system prompt has real content to inject.
-        let ws = rig.workspace().expect("workspace must be available");
+        let ws = Workspace::new_with_db(TEST_USER_ID, rig.database().clone());
         ws.write(
             "IDENTITY.md",
             "I am TestBot, a helpful testing assistant created for E2E verification.",

tests/multi_tenant_system_prompt.rs

@@ -1,10 +1,10 @@
-//! Tests proving that multi-tenant system prompts are broken.
+//! Regression tests for multi-tenant system prompts.
 //!
-//! Bug: In multi-tenant mode, the agent loop uses `self.workspace()` which
-//! returns a single shared workspace (user_id="default"). Identity files
-//! (IDENTITY.md, SOUL.md, USER.md) seeded under per-user IDs ("alice",
-//! "bob") are invisible to this workspace, so the system prompt is
-//! empty/wrong.
+//! The agent must build the conversational system prompt from a workspace
+//! scoped to the incoming message's user, not from the shared owner-scope
+//! workspace created at startup. Otherwise per-user identity files
+//! (IDENTITY.md, SOUL.md, USER.md) become invisible and different users can
+//! see the same owner-scoped prompt.
 //!
 //! These tests:
 //! 1. Seed identity files for two users (alice, bob) in the database
@@ -13,7 +13,7 @@
 //!    correct user's identity
 //! 4. Verify user A's identity doesn't leak into user B's prompt
 //!
-//! All tests are expected to FAIL until the bug is fixed.
+//! These tests ensure each user's identity is isolated correctly.
 
 #[cfg(feature = "libsql")]
 mod support;

tests/openai_compat_integration.rs

@@ -94,6 +94,7 @@ impl LlmProvider for MockLlmProvider {
                     id: "call_mock_001".to_string(),
                     name: tool.name.clone(),
                     arguments: serde_json::json!({"test": true}),
+                    reasoning: None,
                 }],
                 input_tokens: 15,
                 output_tokens: 8,

tests/support/trace_llm.rs

@@ -566,6 +566,7 @@ impl LlmProvider for TraceLlm {
                         id: tc.id,
                         name: tc.name,
                         arguments: tc.arguments,
+                        reasoning: None,
                     })
                     .collect();
                 Ok(ToolCompletionResponse {