chore: add __pycache__ and *.pyc to .gitignore

Prevent Python bytecode from being committed. Several open PRs
accidentally included __pycache__/ directories.

Co-Authored-By: Claude Opus 4.6 (1M context) <[email protected]>

.github/workflows/code_style.yml

@@ -78,15 +78,55 @@ jobs:
     - name: Check lints
       run: cargo clippy --all --benches --tests --examples ${{ matrix.flags }} -- -D warnings
 
+  no-panics:
+    name: No panics in production code
+    runs-on: ubuntu-latest
+    steps:
+    - name: Checkout repository
+      uses: actions/checkout@v6
+      with:
+        fetch-depth: 0
+    - name: Check for .unwrap(), .expect(), assert!() in production code
+      run: |
+        BASE="${{ github.event.pull_request.base.sha }}"
+        # Get added lines in .rs files (production only, exclude tests/)
+        ADDED=$(git diff "$BASE"...HEAD -- 'src/**/*.rs' 'crates/**/*.rs' \
+          | grep -E '^\+[^+]' || true)
+
+        if [ -z "$ADDED" ]; then
+          echo "No production Rust changes detected."
+          exit 0
+        fi
+
+        # Match panic-inducing patterns, excluding test code and safety suppressions
+        VIOLATIONS=$(echo "$ADDED" \
+          | grep -E '\.(unwrap|expect)\(|[^_]assert(_eq|_ne)?!' \
+          | grep -Ev 'debug_assert|// safety:|#\[cfg\(test\)\]|#\[test\]|mod tests' \
+          || true)
+
+        if [ -n "$VIOLATIONS" ]; then
+          echo "::error::Found .unwrap(), .expect(), or assert!() in production code."
+          echo "Production code must use proper error handling instead of panicking."
+          echo "Suppress false positives with an inline '// safety: <reason>' comment."
+          echo ""
+          echo "$VIOLATIONS" | head -20
+          echo ""
+          COUNT=$(echo "$VIOLATIONS" | wc -l | tr -d ' ')
+          echo "Total: $COUNT violation(s)"
+          exit 1
+        fi
+
+        echo "OK: No panic-inducing calls in changed production code."
+
   # Roll-up job for branch protection
   code-style:
     name: Code Style (fmt + clippy + deny)
     runs-on: ubuntu-latest
     if: always()
-    needs: [format, clippy, clippy-windows, deny-check]
+    needs: [format, clippy, clippy-windows, deny-check, no-panics]
     steps:
       - run: |
-          if [[ "${{ needs.format.result }}" != "success" || "${{ needs.clippy.result }}" != "success" || "${{ needs.deny-check.result }}" != "success" ]]; then
+          if [[ "${{ needs.format.result }}" != "success" || "${{ needs.clippy.result }}" != "success" || "${{ needs.deny-check.result }}" != "success" || "${{ needs.no-panics.result }}" != "success" ]]; then
             echo "One or more jobs failed"
             exit 1
           fi

.gitignore

@@ -14,6 +14,10 @@
 
 target/
 
+# Python
+__pycache__/
+*.pyc
+
 # Benchmark results (local runs, not committed)
 bench-results/
 

registry/channels/discord.json

@@ -2,7 +2,7 @@
   "name": "discord",
   "display_name": "Discord Channel",
   "kind": "channel",
-  "version": "0.2.0",
+  "version": "0.2.1",
   "wit_version": "0.3.0",
   "description": "Talk to your agent in Discord",
   "keywords": [

registry/tools/github.json

@@ -2,7 +2,7 @@
   "name": "github",
   "display_name": "GitHub",
   "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
   "wit_version": "0.3.0",
   "description": "GitHub integration for issues, PRs, repos, and code search",
   "keywords": [

registry/tools/web-search.json

@@ -2,7 +2,7 @@
   "name": "web-search",
   "display_name": "Web Search",
   "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
   "wit_version": "0.3.0",
   "description": "Search the web using Brave Search API",
   "keywords": [

scripts/check-boundaries.sh

@@ -70,19 +70,21 @@ echo
 # This is a WARNING, not a hard violation.
 # --------------------------------------------------------------------------
 
-echo "--- Check 2: .unwrap() / .expect() in production code ---"
+echo "--- Check 2: .unwrap() / .expect() / assert!() in production code ---"
 
-# Collect raw matches excluding obvious test-only files and lines
+# Collect raw matches excluding obvious test-only files and lines.
-raw_results=$(grep -rn '\.unwrap()\|\.expect(' src/ \
+# Also catches assert!(), assert_eq!(), assert_ne!() but NOT debug_assert variants.
+raw_results=$(grep -rnE '\.(unwrap|expect)\(|[^_]assert(_eq|_ne)?!' src/ \
     --include='*.rs' \
     | grep -v 'src/main.rs' \
     | grep -v 'src/testing.rs' \
     | grep -v 'src/setup/' \
+    | grep -Ev 'debug_assert|// safety:' \
     || true)
 
 if [ -n "$raw_results" ]; then
     total=$(echo "$raw_results" | wc -l | tr -d ' ')
-    echo "WARNING: ~$total .unwrap()/.expect() calls found in src/ (excluding main/testing/setup)."
+    echo "WARNING: ~$total .unwrap()/.expect()/assert!() calls found in src/ (excluding main/testing/setup)."
     echo "Many are in test modules; a per-file breakdown helps triage:"
     echo
     # Show per-file counts, sorted by count descending, top 15

scripts/pre-commit-safety.sh

@@ -10,6 +10,7 @@
 #   3. Hardcoded /tmp paths in tests (flaky in parallel runs)
 #   4. Tool parameters logged without redaction (secret leaks)
 #   5. Multi-step DB operations without transaction wrapping
+#   6. .unwrap(), .expect(), assert!() in production code (panics)
 #
 # Suppress individual lines with an inline "// safety: <reason>" comment.
 
@@ -128,6 +129,24 @@ if [ -n "$DIFF_W_OUTPUT" ]; then
     fi
 fi
 
+# 6. .unwrap(), .expect(), assert!() in production code
+#    Matches added lines containing panic-inducing calls.
+#    Excludes test files, test modules, and debug_assert (compiled out in release).
+#    Suppress with "// safety: <reason>".
+PROD_DIFF="$DIFF_OUTPUT"
+# Strip hunks from test-only files (tests/ directory, *_test.rs, test_*.rs)
+PROD_DIFF=$(echo "$PROD_DIFF" | grep -v '^+++ b/tests/' || true)
+if echo "$PROD_DIFF" | grep -nE '^\+' \
+    | grep -E '\.(unwrap|expect)\(|[^_]assert(_eq|_ne)?!' \
+    | grep -vE 'debug_assert|// safety:|#\[cfg\(test\)\]|#\[test\]|mod tests' \
+    | head -5 | grep -q .; then
+    warn "PANIC" "Production code must not use .unwrap(), .expect(), or assert!(). Use proper error handling."
+    echo "$PROD_DIFF" | grep -nE '^\+' \
+        | grep -E '\.(unwrap|expect)\(|[^_]assert(_eq|_ne)?!' \
+        | grep -vE 'debug_assert|// safety:|#\[cfg\(test\)\]|#\[test\]|mod tests' \
+        | head -5 | sed 's/^/    /'
+fi
+
 if [ "$WARNINGS" -gt 0 ]; then
     echo ""
     echo "Found $WARNINGS potential issue(s). Fix them or add '// safety: <reason>' to suppress."

src/agent/routine_engine.rs

@@ -93,19 +93,26 @@ impl RoutineEngine {
                 let mut cache = Vec::new();
                 for routine in routines {
                     match &routine.trigger {
-                        Trigger::Event { pattern, .. } => match Regex::new(pattern) {
+                        Trigger::Event { pattern, .. } => {
-                            Ok(re) => cache.push(EventMatcher::Message {
+                            // Use RegexBuilder with size limit to prevent ReDoS
-                                routine: routine.clone(),
+                            // from user-supplied patterns (issue #825).
-                                regex: re,
+                            match regex::RegexBuilder::new(pattern)
-                            }),
+                                .size_limit(64 * 1024) // 64KB compiled size limit
-                            Err(e) => {
+                                .build()
-                                tracing::warn!(
+                            {
-                                    routine = %routine.name,
+                                Ok(re) => cache.push(EventMatcher::Message {
-                                    "Invalid event regex '{}': {}",
+                                    routine: routine.clone(),
-                                    pattern, e
+                                    regex: re,
-                                );
+                                }),
+                                Err(e) => {
+                                    tracing::warn!(
+                                        routine = %routine.name,
+                                        "Invalid or too complex event regex '{}': {}",
+                                        pattern, e
+                                    );
+                                }
                             }
-                        },
+                        }
                         Trigger::SystemEvent { .. } => {
                             cache.push(EventMatcher::System {
                                 routine: routine.clone(),
@@ -973,6 +980,18 @@ async fn execute_lightweight_with_tools(
                     }
                 };
 
+                // Truncate oversized tool output to prevent unbounded context growth.
+                // Routine tool loops are lightweight and should not accumulate
+                // large payloads across iterations.
+                const MAX_TOOL_OUTPUT_CHARS: usize = 8192;
+                let result_content = if result_content.len() > MAX_TOOL_OUTPUT_CHARS {
+                    let truncated = &result_content
+                        [..result_content.floor_char_boundary(MAX_TOOL_OUTPUT_CHARS)];
+                    format!("{truncated}\n... [output truncated to {MAX_TOOL_OUTPUT_CHARS} chars]")
+                } else {
+                    result_content
+                };
+
                 // Add tool result to context
                 messages.push(ChatMessage::tool_result(&tc.id, &tc.name, &result_content));
             }

src/channels/http.rs

@@ -269,21 +269,24 @@ async fn webhook_handler(
     let mut fallback_req = None;
     {
         let webhook_secret = state.webhook_secret.read().await;
-        let Some(expected_secret) = webhook_secret.as_ref() else {
+        let expected_secret = match webhook_secret.as_ref() {
-            return (
+            Some(secret) => secret.expose_secret(),
-                StatusCode::UNAUTHORIZED,
+            None => {
-                Json(WebhookResponse {
+                // No secret configured — reject all requests. This guards against
-                    message_id: Uuid::nil(),
+                // the secret being cleared at runtime via update_secret(None).
-                    status: "error".to_string(),
+                // The start() method also prevents startup without a secret, but
-                    response: Some(
+                // this is defense-in-depth for the SIGHUP hot-swap path.
-                        "Webhook authentication required: HTTP webhook secret is not configured."
+                return (
-                            .to_string(),
+                    StatusCode::SERVICE_UNAVAILABLE,
-                    ),
+                    Json(WebhookResponse {
-                }),
+                        message_id: Uuid::nil(),
-            )
+                        status: "error".to_string(),
-                .into_response();
+                        response: Some("Webhook authentication not configured".to_string()),
+                    }),
+                )
+                    .into_response();
+            }
         };
-        let expected_secret = expected_secret.expose_secret();
 
         match headers.get("x-ironclaw-signature") {
             Some(raw_signature) => match raw_signature.to_str() {
@@ -1085,7 +1088,7 @@ mod tests {
             .unwrap();
 
         let resp = app.oneshot(req).await.unwrap();
-        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+        assert_eq!(resp.status(), StatusCode::SERVICE_UNAVAILABLE); // safety: test assertion
     }
 
     #[tokio::test]
@@ -1206,4 +1209,34 @@ mod tests {
         let body = b"test body content";
         assert!(!verify_hmac_signature(secret, body, "sha256=not-hex!"));
     }
+
+    /// Regression test for issue #1033: when the webhook secret is cleared at
+    /// runtime via update_secret(None), subsequent requests must be rejected
+    /// instead of being processed without authentication.
+    #[tokio::test]
+    async fn webhook_rejects_when_secret_cleared_at_runtime() {
+        let channel = test_channel(Some("initial-secret"));
+        let _stream = channel.start().await.unwrap();
+
+        // Clear the secret at runtime (simulates a bad SIGHUP config reload)
+        channel.update_secret(None).await;
+
+        let app = channel.routes();
+        let body = serde_json::json!({
+            "content": "hello"
+        });
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .body(Body::from(serde_json::to_vec(&body).unwrap()))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::SERVICE_UNAVAILABLE,
+            "requests must be rejected when webhook secret is cleared at runtime"
+        );
+    }
 }

src/channels/relay/channel.rs

@@ -294,6 +294,8 @@ impl Channel for RelayChannel {
                 match client.connect_stream(&token, stream_timeout_secs).await {
                     Ok((new_stream, new_parser)) => {
                         tracing::info!("Relay SSE stream reconnected");
+                        consecutive_failures = 0;
+                        backoff_ms = backoff_initial_ms;
                         current_stream = new_stream;
                         // Abort old parser before replacing
                         if let Some(old) = parser_handle.write().await.take() {
@@ -312,6 +314,8 @@ impl Channel for RelayChannel {
                                         tracing::info!(
                                             "Relay SSE stream reconnected with new token"
                                         );
+                                        consecutive_failures = 0;
+                                        backoff_ms = backoff_initial_ms;
                                         current_stream = new_stream;
                                         if let Some(old) = parser_handle.write().await.take() {
                                             old.abort();

src/channels/web/handlers/routines.rs

@@ -190,12 +190,21 @@ pub async fn routines_toggle_handler(
         None => !routine.enabled,
     };
 
+    // When re-enabling a cron routine, recompute next_fire_at so the cron
+    // ticker can pick it up. Mirrors the CLI behavior (issue #1077).
     if routine.enabled
         && !was_enabled
-        && let Trigger::Cron { schedule, timezone } = &routine.trigger
+        && let Trigger::Cron {
+            ref schedule,
+            ref timezone,
+        } = routine.trigger
     {
-        routine.next_fire_at = next_cron_fire(schedule, timezone.as_deref())
+        routine.next_fire_at = next_cron_fire(schedule, timezone.as_deref()).map_err(|e| {
-            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Failed to compute next fire: {e}"),
+            )
+        })?;
     }
 
     store
@@ -203,6 +212,12 @@ pub async fn routines_toggle_handler(
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
+    // Refresh the in-memory event trigger cache so event/system_event
+    // routines reflect the new enabled state immediately (issue #1076).
+    if let Some(engine) = state.routine_engine.read().await.as_ref() {
+        engine.refresh_event_cache().await;
+    }
+
     Ok(Json(serde_json::json!({
         "status": if routine.enabled { "enabled" } else { "disabled" },
         "routine_id": routine_id,
@@ -227,6 +242,12 @@ pub async fn routines_delete_handler(
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
     if deleted {
+        // Refresh the in-memory event trigger cache so deleted event/system_event
+        // routines stop firing immediately (issue #1076).
+        if let Some(engine) = state.routine_engine.read().await.as_ref() {
+            engine.refresh_event_cache().await;
+        }
+
         Ok(Json(serde_json::json!({
             "status": "deleted",
             "routine_id": routine_id,

src/channels/web/static/app.js

@@ -434,8 +434,7 @@ function sendMessage() {
   const content = input.value.trim();
   if (!content && stagedImages.length === 0) return;
 
-  const imagesToDisplay = stagedImages.slice(); // snapshot before clearing
+  addMessage('user', content || '(images attached)');
-  addMessage('user', content, imagesToDisplay);
   input.value = '';
   autoResizeTextarea(input);
   input.focus();
@@ -541,24 +540,6 @@ document.getElementById('chat-input').addEventListener('paste', (e) => {
   }
 });
 
-document.getElementById('chat-input').addEventListener('dragover', (e) => {
-  const hasImage = Array.from(e.dataTransfer.items || []).some(
-    item => item.kind === 'file' && item.type.startsWith('image/')
-  );
-  if (hasImage) {
-    e.preventDefault();
-    e.dataTransfer.dropEffect = 'copy';
-  }
-});
-
-document.getElementById('chat-input').addEventListener('drop', (e) => {
-  const files = Array.from(e.dataTransfer.files || []).filter(f => f.type.startsWith('image/'));
-  if (files.length > 0) {
-    e.preventDefault();
-    handleImageFiles(files);
-  }
-});
-
 function addGeneratedImage(dataUrl, path) {
   const container = document.getElementById('chat-messages');
   const card = document.createElement('div');
@@ -733,32 +714,9 @@ function copyMessage(btn) {
   });
 }
 
-function addMessage(role, content, images) {
+function addMessage(role, content) {
   const container = document.getElementById('chat-messages');
-  const div = document.createElement('div');
+  const div = createMessageElement(role, content);
-  div.className = 'message ' + role;
-  if (role === 'user') {
-    if (images && images.length > 0) {
-      const imgStrip = document.createElement('div');
-      imgStrip.className = 'message-images';
-      images.forEach(img => {
-        const thumb = document.createElement('img');
-        thumb.className = 'message-image-thumb';
-        thumb.src = img.dataUrl;
-        thumb.alt = 'Attached image';
-        imgStrip.appendChild(thumb);
-      });
-      div.appendChild(imgStrip);
-    }
-    if (content) {
-      const textDiv = document.createElement('div');
-      textDiv.textContent = content;
-      div.appendChild(textDiv);
-    }
-  } else {
-    div.setAttribute('data-raw', content);
-    div.innerHTML = renderMarkdown(content);
-  }
   container.appendChild(div);
   container.scrollTop = container.scrollHeight;
 }

src/channels/web/static/style.css

@@ -3903,9 +3903,8 @@ mark {
   display: flex;
   flex-direction: row;
   gap: 8px;
-  padding: 10px 4px 4px;
+  padding: 4px;
   overflow-x: auto;
-  overflow-y: visible;
   min-height: 0;
   width: 100%;
 }
@@ -3926,7 +3925,6 @@ mark {
   border-radius: 6px;
   object-fit: cover;
   display: block;
-  border: 1px solid var(--border);
 }
 
 .image-preview-remove {
@@ -3935,41 +3933,21 @@ mark {
   right: -6px;
   width: 18px;
   height: 18px;
-  padding: 4px !important;
   border-radius: 50%;
   background: var(--danger);
   color: #fff;
-  border: 2px solid var(--bg-secondary);
+  border: none;
-  font-size: 10px;
+  font-size: 12px;
-  line-height: 14px;
+  line-height: 18px;
   text-align: center;
   cursor: pointer;
   padding: 0;
-  display: flex;
-  align-items: center;
-  justify-content: center;
 }
 
 .image-preview-remove:hover {
   background: #c33;
 }
 
-/* Images in user message bubbles */
-.message.user .message-images {
-  display: flex;
-  flex-wrap: wrap;
-  gap: 6px;
-  margin-bottom: 4px;
-}
-
-.message.user .message-image-thumb {
-  max-width: 240px;
-  max-height: 200px;
-  border-radius: 8px;
-  object-fit: cover;
-  display: block;
-}
-
 /* Generated Image */
 .generated-image-card {
   max-width: 512px;

src/tools/builtin/http.rs

@@ -214,6 +214,7 @@ fn is_disallowed_ipv4(v4: &Ipv4Addr) -> bool {
         || v4.is_multicast()
         || v4.is_unspecified()
         || *v4 == Ipv4Addr::new(169, 254, 169, 254)
+        || (v4.octets()[0] == 100 && (v4.octets()[1] & 0xC0) == 64)
 }
 
 fn is_disallowed_ip(ip: &IpAddr) -> bool {
@@ -913,6 +914,8 @@ mod tests {
         assert!(is_disallowed_ip(&IpAddr::V4(Ipv4Addr::new(
             169, 254, 169, 254
         ))));
+        // Carrier-grade NAT
+        assert!(is_disallowed_ip(&IpAddr::V4(Ipv4Addr::new(100, 64, 0, 1))));
         // Public
         assert!(!is_disallowed_ip(&IpAddr::V4(Ipv4Addr::new(8, 8, 8, 8))));
     }

src/tools/builtin/routine.rs

@@ -24,6 +24,132 @@ use crate::context::JobContext;
 use crate::db::Database;
 use crate::tools::tool::{ApprovalRequirement, Tool, ToolError, ToolOutput, require_str};
 
+pub(crate) fn routine_create_parameters_schema() -> serde_json::Value {
+    serde_json::json!({
+        "type": "object",
+        "properties": {
+            "name": {
+                "type": "string",
+                "description": "Unique routine name, for example 'daily-pr-review'."
+            },
+            "description": {
+                "type": "string",
+                "description": "Short summary of what the routine is for."
+            },
+            "trigger_type": {
+                "type": "string",
+                "enum": ["cron", "event", "system_event", "manual"],
+                "description": "When the routine fires: 'cron' for schedules, 'event' for incoming messages, 'system_event' for structured emitted events, or 'manual' for explicit runs."
+            },
+            "schedule": {
+                "type": "string",
+                "description": "Cron schedule for 'cron' triggers. Uses 6 fields: second minute hour day month weekday."
+            },
+            "event_pattern": {
+                "type": "string",
+                "description": "Regex matched against incoming message text for 'event' triggers, for example '^bug\\\\b'."
+            },
+            "event_channel": {
+                "type": "string",
+                "description": "Optional platform filter for 'event' triggers, for example 'telegram'. Omit to match any channel. Not a chat or thread ID."
+            },
+            "event_source": {
+                "type": "string",
+                "description": "Structured event source for 'system_event' triggers, for example 'github'."
+            },
+            "event_type": {
+                "type": "string",
+                "description": "Structured event type for 'system_event' triggers, for example 'issue.opened'."
+            },
+            "event_filters": {
+                "type": "object",
+                "properties": {},
+                "additionalProperties": {
+                    "type": ["string", "number", "boolean"]
+                },
+                "description": "Optional exact-match payload filters for 'system_event' triggers. Values can be strings, numbers, or booleans."
+            },
+            "prompt": {
+                "type": "string",
+                "description": "Instructions for what the routine should do after it fires."
+            },
+            "context_paths": {
+                "type": "array",
+                "items": { "type": "string" },
+                "description": "Workspace paths to load as extra context before running the routine."
+            },
+            "action_type": {
+                "type": "string",
+                "enum": ["lightweight", "full_job"],
+                "description": "Execution mode: 'lightweight' for one LLM turn or 'full_job' for a multi-step job with tools."
+            },
+            "use_tools": {
+                "type": "boolean",
+                "description": "Enable safe tool use in 'lightweight' mode. Ignored for 'full_job'."
+            },
+            "max_tool_rounds": {
+                "type": "integer",
+                "description": "Maximum tool-call rounds in 'lightweight' mode when 'use_tools' is true."
+            },
+            "cooldown_secs": {
+                "type": "integer",
+                "description": "Minimum seconds between fires."
+            },
+            "tool_permissions": {
+                "type": "array",
+                "items": { "type": "string" },
+                "description": "Pre-authorized tool names for 'full_job' routines."
+            },
+            "notify_channel": {
+                "type": "string",
+                "description": "Where routine output should be sent, for example 'telegram' or 'slack'. This does not control what triggers the routine."
+            },
+            "notify_user": {
+                "type": "string",
+                "description": "User or destination to notify, for example a username or chat ID."
+            },
+            "timezone": {
+                "type": "string",
+                "description": "IANA timezone used to evaluate 'cron' schedules, for example 'America/New_York'."
+            }
+        },
+        "required": ["name", "trigger_type", "prompt"]
+    })
+}
+
+pub(crate) fn routine_update_parameters_schema() -> serde_json::Value {
+    serde_json::json!({
+        "type": "object",
+        "properties": {
+            "name": {
+                "type": "string",
+                "description": "Name of the routine to update."
+            },
+            "enabled": {
+                "type": "boolean",
+                "description": "Set to true to enable the routine or false to disable it."
+            },
+            "prompt": {
+                "type": "string",
+                "description": "Replace the routine instructions for what it should do after it fires."
+            },
+            "schedule": {
+                "type": "string",
+                "description": "New cron schedule for existing 'cron' routines only. This does not convert other trigger types."
+            },
+            "timezone": {
+                "type": "string",
+                "description": "New IANA timezone for existing 'cron' routines only, for example 'America/New_York'."
+            },
+            "description": {
+                "type": "string",
+                "description": "Replace the routine summary."
+            }
+        },
+        "required": ["name"]
+    })
+}
+
 // ==================== routine_create ====================
 
 pub struct RoutineCreateTool {
@@ -50,92 +176,7 @@ impl Tool for RoutineCreateTool {
     }
 
     fn parameters_schema(&self) -> serde_json::Value {
-        serde_json::json!({
+        routine_create_parameters_schema()
-            "type": "object",
-            "properties": {
-                "name": {
-                    "type": "string",
-                    "description": "Unique name for the routine (e.g. 'daily-pr-review')"
-                },
-                "description": {
-                    "type": "string",
-                    "description": "What this routine does"
-                },
-                "trigger_type": {
-                    "type": "string",
-                    "enum": ["cron", "event", "system_event", "manual"],
-                    "description": "When the routine fires"
-                },
-                "schedule": {
-                    "type": "string",
-                    "description": "Cron expression (for cron trigger). E.g. '0 9 * * MON-FRI' for weekdays at 9am. Uses 6-field cron (sec min hour day month weekday)."
-                },
-                "event_pattern": {
-                    "type": "string",
-                    "description": "Regex pattern to match messages (for event trigger)"
-                },
-                "event_channel": {
-                    "type": "string",
-                    "description": "Optional channel filter for event trigger (e.g. 'telegram')"
-                },
-                "event_source": {
-                    "type": "string",
-                    "description": "Event source for system_event triggers (e.g. 'github')"
-                },
-                "event_type": {
-                    "type": "string",
-                    "description": "Event type for system_event triggers (e.g. 'issue.opened')"
-                },
-                "event_filters": {
-                    "type": "object",
-                    "description": "Optional exact-match filters against payload fields for system_event triggers. Values can be strings, numbers, or booleans."
-                },
-                "prompt": {
-                    "type": "string",
-                    "description": "The prompt/instructions for the routine"
-                },
-                "context_paths": {
-                    "type": "array",
-                    "items": { "type": "string" },
-                    "description": "Workspace paths to load as context (e.g. ['context/priorities.md'])"
-                },
-                "action_type": {
-                    "type": "string",
-                    "enum": ["lightweight", "full_job"],
-                    "description": "Execution mode: 'lightweight' (single LLM call, default) or 'full_job' (multi-turn with tools)"
-                },
-                "use_tools": {
-                    "type": "boolean",
-                    "description": "Enable tool access in lightweight mode (default: false). Only safe tools (no approval required) are available. Ignored for full_job mode."
-                },
-                "max_tool_rounds": {
-                    "type": "integer",
-                    "description": "Max tool call rounds in lightweight mode (default: 3). Only used when use_tools is true."
-                },
-                "cooldown_secs": {
-                    "type": "integer",
-                    "description": "Minimum seconds between fires (default: 300)"
-                },
-                "tool_permissions": {
-                    "type": "array",
-                    "items": { "type": "string" },
-                    "description": "Tool names pre-authorized for Always-approval tools in full_job mode (e.g. ['shell']). UnlessAutoApproved tools are automatically permitted in routines."
-                },
-                "notify_channel": {
-                    "type": "string",
-                    "description": "Channel to send results to (e.g. 'telegram', 'slack', 'tui'). Sets the default channel for message tool calls in routine jobs."
-                },
-                "notify_user": {
-                    "type": "string",
-                    "description": "User/target to notify (e.g. username, chat ID). Defaults to 'default'."
-                },
-                "timezone": {
-                    "type": "string",
-                    "description": "IANA timezone for cron schedule evaluation (e.g. 'America/New_York'). Defaults to UTC."
-                }
-            },
-            "required": ["name", "trigger_type", "prompt"]
-        })
     }
 
     async fn execute(
@@ -199,9 +240,13 @@ impl Tool for RoutineCreateTool {
                             "event trigger requires 'event_pattern'".to_string(),
                         )
                     })?;
-                // Validate regex
+                // Validate regex with size limit to prevent ReDoS (issue #825)
-                regex::Regex::new(pattern)
+                regex::RegexBuilder::new(pattern)
-                    .map_err(|e| ToolError::InvalidParameters(format!("invalid regex: {e}")))?;
+                    .size_limit(64 * 1024)
+                    .build()
+                    .map_err(|e| {
+                        ToolError::InvalidParameters(format!("invalid or too complex regex: {e}"))
+                    })?;
                 let channel = params
                     .get("event_channel")
                     .and_then(|v| v.as_str())
@@ -478,41 +523,13 @@ impl Tool for RoutineUpdateTool {
     }
 
     fn description(&self) -> &str {
-        "Update an existing routine. Can modify trigger, prompt, schedule, or toggle enabled state. \
+        "Update an existing routine. Can change prompt, description, enabled state, or cron timing. \
-         Pass the routine name and only the fields you want to change."
+         Pass the routine name and only the fields you want to change. \
+         This does not convert one trigger type into another."
     }
 
     fn parameters_schema(&self) -> serde_json::Value {
-        serde_json::json!({
+        routine_update_parameters_schema()
-            "type": "object",
-            "properties": {
-                "name": {
-                    "type": "string",
-                    "description": "Name of the routine to update"
-                },
-                "enabled": {
-                    "type": "boolean",
-                    "description": "Enable or disable the routine"
-                },
-                "prompt": {
-                    "type": "string",
-                    "description": "New prompt/instructions"
-                },
-                "schedule": {
-                    "type": "string",
-                    "description": "New cron schedule (for cron triggers)"
-                },
-                "timezone": {
-                    "type": "string",
-                    "description": "IANA timezone for cron schedule (e.g. 'America/New_York'). Only valid for cron triggers."
-                },
-                "description": {
-                    "type": "string",
-                    "description": "New description"
-                }
-            },
-            "required": ["name"]
-        })
     }
 
     async fn execute(
@@ -953,3 +970,117 @@ impl Tool for EventEmitTool {
         true
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::{routine_create_parameters_schema, routine_update_parameters_schema};
+    use crate::tools::validate_tool_schema;
+
+    fn property<'a>(schema: &'a serde_json::Value, name: &str) -> &'a serde_json::Value {
+        schema
+            .get("properties")
+            .and_then(|props| props.get(name))
+            .unwrap_or_else(|| panic!("missing schema property {name}"))
+    }
+
+    #[test]
+    fn routine_create_schema_exposes_all_trigger_and_delivery_fields() {
+        let schema = routine_create_parameters_schema();
+        let errors = validate_tool_schema(&schema, "routine_create");
+        assert!(
+            errors.is_empty(),
+            "routine_create schema should validate cleanly: {errors:?}"
+        );
+
+        for field in [
+            "trigger_type",
+            "schedule",
+            "event_pattern",
+            "event_channel",
+            "event_source",
+            "event_type",
+            "event_filters",
+            "action_type",
+            "use_tools",
+            "max_tool_rounds",
+            "tool_permissions",
+            "notify_channel",
+            "notify_user",
+            "timezone",
+        ] {
+            let _ = property(&schema, field);
+        }
+    }
+
+    #[test]
+    fn routine_create_schema_descriptions_cover_event_trigger_gotchas() {
+        let schema = routine_create_parameters_schema();
+
+        let trigger_type = property(&schema, "trigger_type")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("trigger_type description");
+        assert!(trigger_type.contains("incoming messages"));
+        assert!(trigger_type.contains("structured emitted events"));
+
+        let event_pattern = property(&schema, "event_pattern")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("event_pattern description");
+        assert!(event_pattern.contains("incoming message text"));
+        assert!(event_pattern.contains("^bug\\\\b"));
+
+        let event_channel = property(&schema, "event_channel")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("event_channel description");
+        assert!(event_channel.contains("Omit to match any channel"));
+        assert!(event_channel.contains("Not a chat or thread ID"));
+
+        let notify_channel = property(&schema, "notify_channel")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("notify_channel description");
+        assert!(notify_channel.contains("does not control what triggers"));
+
+        let prompt = property(&schema, "prompt")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("prompt description");
+        assert!(prompt.contains("after it fires"));
+    }
+
+    #[test]
+    fn routine_update_schema_exposes_supported_fields_and_limits() {
+        let schema = routine_update_parameters_schema();
+        let errors = validate_tool_schema(&schema, "routine_update");
+        assert!(
+            errors.is_empty(),
+            "routine_update schema should validate cleanly: {errors:?}"
+        );
+
+        for field in [
+            "name",
+            "enabled",
+            "prompt",
+            "schedule",
+            "timezone",
+            "description",
+        ] {
+            let _ = property(&schema, field);
+        }
+
+        let schedule = property(&schema, "schedule")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("schedule description");
+        assert!(schedule.contains("existing 'cron' routines only"));
+        assert!(schedule.contains("does not convert other trigger types"));
+
+        let timezone = property(&schema, "timezone")
+            .get("description")
+            .and_then(|value| value.as_str())
+            .expect("timezone description");
+        assert!(timezone.contains("existing 'cron' routines only"));
+    }
+}

src/tools/builtin/time.rs

@@ -247,7 +247,11 @@ fn resolve_timezone_for_output(
     params: &serde_json::Value,
     ctx: &JobContext,
 ) -> Result<Option<(Tz, String)>, ToolError> {
-    if let Some(name) = params.get("timezone").and_then(|v| v.as_str()) {
+    if let Some(name) = params
+        .get("timezone")
+        .and_then(|v| v.as_str())
+        .filter(|s| !s.is_empty())
+    {
         let tz = parse_timezone(name)?;
         return Ok(Some((tz, tz.to_string())));
     }
@@ -286,7 +290,11 @@ fn context_timezone(ctx: &JobContext) -> Result<Option<(Tz, String)>, ToolError>
 
 fn optional_timezone(params: &serde_json::Value, keys: &[&str]) -> Result<Option<Tz>, ToolError> {
     for key in keys {
-        if let Some(value) = params.get(*key).and_then(|v| v.as_str()) {
+        if let Some(value) = params
+            .get(*key)
+            .and_then(|v| v.as_str())
+            .filter(|s| !s.is_empty())
+        {
             return parse_timezone(value).map(Some);
         }
     }
@@ -534,4 +542,48 @@ mod tests {
 
         assert_eq!(dt.to_rfc3339(), "2026-03-08T07:30:00+00:00");
     }
+
+    #[tokio::test]
+    async fn test_now_with_empty_timezone_string_does_not_error() {
+        // LLMs sometimes pass "" for optional fields instead of omitting them.
+        // Empty timezone should be treated as absent and fall back to UTC.
+        let tool = TimeTool;
+        let ctx = JobContext::with_user("test", "chat", "test");
+
+        let output = tool
+            .execute(
+                serde_json::json!({
+                    "operation": "now",
+                    "timezone": ""
+                }),
+                &ctx,
+            )
+            .await
+            .expect("empty timezone string should not error");
+
+        assert!(output.result.get("iso").is_some(), "should have iso");
+    }
+
+    #[tokio::test]
+    async fn test_convert_with_empty_from_timezone_string_does_not_error() {
+        // LLMs sometimes pass "" for optional fields instead of omitting them.
+        // Empty from_timezone should be treated as absent.
+        let tool = TimeTool;
+        let ctx = JobContext::with_user("test", "chat", "test");
+
+        let output = tool
+            .execute(
+                serde_json::json!({
+                    "operation": "convert",
+                    "timestamp": "2026-03-08T12:00:00Z",
+                    "to_timezone": "America/New_York",
+                    "from_timezone": ""
+                }),
+                &ctx,
+            )
+            .await
+            .expect("empty from_timezone string should not error");
+
+        assert!(output.result.get("output").is_some(), "should have output");
+    }
 }

src/tools/mcp/auth.rs

@@ -18,6 +18,44 @@ use crate::cli::oauth_defaults::{self, OAUTH_CALLBACK_PORT};
 use crate::secrets::{CreateSecretParams, SecretsStore};
 use crate::tools::mcp::config::McpServerConfig;
 
+/// Shared HTTP client for all OAuth/discovery requests.
+///
+/// Redirects are disabled for security (prevents redirect-based SSRF).
+/// Per-request timeouts can override the default via `.timeout()` on
+/// the request builder.
+fn oauth_http_client() -> Result<&'static reqwest::Client, AuthError> {
+    static CLIENT: std::sync::OnceLock<Result<reqwest::Client, String>> =
+        std::sync::OnceLock::new();
+    CLIENT
+        .get_or_init(|| {
+            reqwest::Client::builder()
+                .timeout(Duration::from_secs(30))
+                .redirect(reqwest::redirect::Policy::none())
+                .build()
+                .map_err(|e| e.to_string())
+        })
+        .as_ref()
+        .map_err(|e| AuthError::Http(e.clone()))
+}
+
+/// Log a debug message when a discovery/auth response is a redirect.
+/// Helps users diagnose configuration issues when legitimate servers
+/// redirect and our no-redirect policy causes a failure.
+fn log_redirect_if_applicable(url: &str, response: &reqwest::Response) {
+    if response.status().is_redirection() {
+        let location = response
+            .headers()
+            .get("location")
+            .and_then(|v| v.to_str().ok());
+        tracing::debug!(
+            "OAuth request to '{}' returned redirect {} -> {:?} (redirects disabled for security)",
+            url,
+            response.status(),
+            location
+        );
+    }
+}
+
 /// OAuth authorization error.
 #[derive(Debug, thiserror::Error)]
 pub enum AuthError {
@@ -287,10 +325,8 @@ async fn validate_url_safe(url: &str) -> Result<(), AuthError> {
         )));
     }
     if scheme == "http" {
-        let host = parsed.host_str().unwrap_or("");
+        if !crate::tools::mcp::config::is_localhost_url(url) {
-        let is_localhost =
+            let host = parsed.host_str().unwrap_or("");
-            host == "localhost" || host == "127.0.0.1" || host == "::1" || host == "[::1]";
-        if !is_localhost {
             return Err(AuthError::DiscoveryFailed(format!(
                 "HTTP is only allowed for localhost; use HTTPS for '{}'",
                 host
@@ -382,18 +418,17 @@ fn parse_resource_metadata_url(www_authenticate: &str) -> Option<String> {
 async fn fetch_resource_metadata(url: &str) -> Result<ProtectedResourceMetadata, AuthError> {
     validate_url_safe(url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(10))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let response = client
         .get(url)
+        .timeout(Duration::from_secs(10))
         .send()
         .await
         .map_err(|e| AuthError::DiscoveryFailed(e.to_string()))?;
 
+    log_redirect_if_applicable(url, &response);
+
     if !response.status().is_success() {
         return Err(AuthError::DiscoveryFailed(format!(
             "HTTP {}",
@@ -411,20 +446,19 @@ async fn fetch_resource_metadata(url: &str) -> Result<ProtectedResourceMetadata,
 async fn discover_via_401(server_url: &str) -> Result<AuthorizationServerMetadata, AuthError> {
     validate_url_safe(server_url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(10))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let response = client
         .post(server_url)
+        .timeout(Duration::from_secs(10))
         .header("Content-Type", "application/json")
         .body("{}")
         .send()
         .await
         .map_err(|e| AuthError::DiscoveryFailed(e.to_string()))?;
 
+    log_redirect_if_applicable(server_url, &response);
+
     if response.status().as_u16() != 401 {
         return Err(AuthError::DiscoveryFailed(format!(
             "Expected 401, got {}",
@@ -472,20 +506,19 @@ pub async fn discover_protected_resource(
 ) -> Result<ProtectedResourceMetadata, AuthError> {
     validate_url_safe(server_url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(10))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let well_known_url = build_well_known_uri(server_url, "oauth-protected-resource")?;
 
     let response = client
         .get(&well_known_url)
+        .timeout(Duration::from_secs(10))
         .send()
         .await
         .map_err(|e| AuthError::DiscoveryFailed(e.to_string()))?;
 
+    log_redirect_if_applicable(&well_known_url, &response);
+
     if !response.status().is_success() {
         return Err(AuthError::NotSupported);
     }
@@ -502,20 +535,19 @@ pub async fn discover_authorization_server(
 ) -> Result<AuthorizationServerMetadata, AuthError> {
     validate_url_safe(auth_server_url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(10))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let well_known_url = build_well_known_uri(auth_server_url, "oauth-authorization-server")?;
 
     let response = client
         .get(&well_known_url)
+        .timeout(Duration::from_secs(10))
         .send()
         .await
         .map_err(|e| AuthError::DiscoveryFailed(e.to_string()))?;
 
+    log_redirect_if_applicable(&well_known_url, &response);
+
     if !response.status().is_success() {
         return Err(AuthError::DiscoveryFailed(format!(
             "HTTP {}",
@@ -595,11 +627,7 @@ pub async fn register_client(
 ) -> Result<ClientRegistrationResponse, AuthError> {
     validate_url_safe(registration_endpoint).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(30))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let request = ClientRegistrationRequest {
         client_name: "IronClaw".to_string(),
@@ -813,7 +841,7 @@ pub fn build_authorization_url(
     if let Some(pkce) = pkce {
         url.push_str(&format!(
             "&code_challenge={}&code_challenge_method=S256",
-            pkce.challenge
+            urlencoding::encode(&pkce.challenge)
         ));
     }
 
@@ -863,11 +891,7 @@ pub async fn exchange_code_for_token(
 ) -> Result<AccessToken, AuthError> {
     validate_url_safe(token_url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(30))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     let mut params = vec![
         ("grant_type", "authorization_code".to_string()),
@@ -1054,11 +1078,7 @@ pub async fn refresh_access_token(
 
     validate_url_safe(&token_url).await?;
 
-    let client = reqwest::Client::builder()
+    let client = oauth_http_client()?;
-        .timeout(Duration::from_secs(30))
-        .redirect(reqwest::redirect::Policy::none())
-        .build()
-        .map_err(|e| AuthError::Http(e.to_string()))?;
 
     // Compute canonical resource URI for RFC 8707
     let resource = canonical_resource_uri(&server_config.url);

src/tools/mcp/client.rs

@@ -5,7 +5,7 @@
 
 use std::collections::HashMap;
 use std::sync::Arc;
-use std::sync::atomic::{AtomicBool, AtomicU64, Ordering};
+use std::sync::atomic::{AtomicU64, Ordering};
 
 use async_trait::async_trait;
 use tokio::sync::RwLock;
@@ -58,9 +58,10 @@ pub struct McpClient {
     /// Custom headers to include in every request.
     custom_headers: HashMap<String, String>,
 
-    /// Whether the MCP initialize handshake has completed.
+    /// Ensures the MCP initialize handshake runs exactly once.
-    /// Used as a local idempotency guard when no session_manager is present.
+    /// Uses `OnceCell` to serialize concurrent callers so only one
-    initialized: AtomicBool,
+    /// actually sends the request; subsequent calls return immediately.
+    initialized: tokio::sync::OnceCell<InitializeResult>,
 }
 
 impl McpClient {
@@ -83,7 +84,7 @@ impl McpClient {
             user_id: "default".to_string(),
             server_config: None,
             custom_headers: HashMap::new(),
-            initialized: AtomicBool::new(false),
+            initialized: tokio::sync::OnceCell::new(),
         }
     }
 
@@ -106,7 +107,7 @@ impl McpClient {
             user_id: "default".to_string(),
             server_config: None,
             custom_headers: HashMap::new(),
-            initialized: AtomicBool::new(false),
+            initialized: tokio::sync::OnceCell::new(),
         }
     }
 
@@ -114,20 +115,24 @@ impl McpClient {
     ///
     /// Use this when you have an `McpServerConfig` with custom headers but no OAuth.
     /// The config must use HTTP transport (the default); for stdio/UDS use `new_with_transport`.
-    pub fn new_with_config(config: McpServerConfig) -> Self {
+    ///
-        assert!(
+    /// Returns an error if the config uses a non-HTTP transport.
-            matches!(
+    pub fn new_with_config(config: McpServerConfig) -> Result<Self, ToolError> {
-                config.effective_transport(),
+        if !matches!(
-                crate::tools::mcp::config::EffectiveTransport::Http
+            config.effective_transport(),
-            ),
+            crate::tools::mcp::config::EffectiveTransport::Http
-            "new_with_config only supports HTTP transport; use new_with_transport for stdio/UDS"
+        ) {
-        );
+            return Err(ToolError::InvalidParameters(
+                "new_with_config only supports HTTP transport; use new_with_transport for stdio/UDS"
+                    .to_string(),
+            ));
+        }
         let transport = Arc::new(HttpMcpTransport::new(
             config.url.clone(),
             config.name.clone(),
         ));
 
-        Self {
+        Ok(Self {
             transport,
             server_url: config.url.clone(),
             server_name: config.name.clone(),
@@ -137,9 +142,9 @@ impl McpClient {
             secrets: None,
             user_id: "default".to_string(),
             custom_headers: config.headers.clone(),
-            initialized: AtomicBool::new(false),
+            initialized: tokio::sync::OnceCell::new(),
             server_config: Some(config),
-        }
+        })
     }
 
     /// Create a new authenticated MCP client.
@@ -169,7 +174,7 @@ impl McpClient {
             user_id: user_id.into(),
             server_config: Some(config),
             custom_headers,
-            initialized: AtomicBool::new(false),
+            initialized: tokio::sync::OnceCell::new(),
         }
     }
 
@@ -205,7 +210,7 @@ impl McpClient {
             user_id: user_id.into(),
             server_config,
             custom_headers,
-            initialized: AtomicBool::new(false),
+            initialized: tokio::sync::OnceCell::new(),
         }
     }
 
@@ -336,53 +341,64 @@ impl McpClient {
     }
 
     /// Initialize the connection to the MCP server.
+    ///
+    /// Uses `OnceCell` to guarantee that exactly one caller performs the
+    /// handshake, even under concurrent access. Subsequent calls return
+    /// immediately.
     pub async fn initialize(&self) -> Result<InitializeResult, ToolError> {
-        // Fast path: already initialized (local flag or session manager)
+        let result = self
-        if self.initialized.load(Ordering::Relaxed) {
+            .initialized
-            return Ok(InitializeResult::default());
+            .get_or_try_init(|| async {
-        }
+                if let Some(ref session_manager) = self.session_manager
-        if let Some(ref session_manager) = self.session_manager
+                    && session_manager.is_initialized(&self.server_name).await
-            && session_manager.is_initialized(&self.server_name).await
+                {
-        {
+                    return Ok(InitializeResult::default());
-            self.initialized.store(true, Ordering::Relaxed);
+                }
-            return Ok(InitializeResult::default());
+                if let Some(ref session_manager) = self.session_manager {
-        }
+                    session_manager
-        if let Some(ref session_manager) = self.session_manager {
+                        .get_or_create(&self.server_name, &self.server_url)
-            session_manager
+                        .await;
-                .get_or_create(&self.server_name, &self.server_url)
+                }
-                .await;
-        }
 
-        let request = McpRequest::initialize(self.next_request_id());
+                let request = McpRequest::initialize(self.next_request_id());
-        let response = self.send_request(request).await?;
+                let response = self.send_request(request).await?;
 
-        if let Some(error) = response.error {
+                if let Some(error) = response.error {
-            return Err(ToolError::ExternalService(format!(
+                    return Err(ToolError::ExternalService(format!(
-                "MCP initialization error: {} (code {})",
+                        "MCP initialization error: {} (code {})",
-                error.message, error.code
+                        error.message, error.code
-            )));
+                    )));
-        }
+                }
 
-        let result: InitializeResult = response
+                let init_result: InitializeResult = response
-            .result
+                    .result
-            .ok_or_else(|| {
+                    .ok_or_else(|| {
-                ToolError::ExternalService("No result in initialize response".to_string())
+                        ToolError::ExternalService("No result in initialize response".to_string())
+                    })
+                    .and_then(|r| {
+                        serde_json::from_value(r).map_err(|e| {
+                            ToolError::ExternalService(format!("Invalid initialize result: {}", e))
+                        })
+                    })?;
+
+                if let Some(ref session_manager) = self.session_manager {
+                    session_manager.mark_initialized(&self.server_name).await;
+                }
+
+                let notification = McpRequest::initialized_notification();
+                if let Err(e) = self.send_request(notification).await {
+                    tracing::debug!(
+                        "Failed to send initialized notification to '{}': {}",
+                        self.server_name,
+                        e
+                    );
+                }
+
+                Ok(init_result)
             })
-            .and_then(|r| {
+            .await?;
-                serde_json::from_value(r).map_err(|e| {
-                    ToolError::ExternalService(format!("Invalid initialize result: {}", e))
-                })
-            })?;
 
-        if let Some(ref session_manager) = self.session_manager {
+        Ok(result.clone())
-            session_manager.mark_initialized(&self.server_name).await;
-        }
-        self.initialized.store(true, Ordering::Relaxed);
-
-        let notification = McpRequest::initialized_notification();
-        let _ = self.send_request(notification).await;
-
-        Ok(result)
     }
 
     /// List available tools from the MCP server.
@@ -471,6 +487,11 @@ impl McpClient {
     }
 }
 
+/// Clone the client, resetting the tools cache and initialization state.
+/// The cloned client shares the same transport and session manager, so
+/// re-initialization will short-circuit via the session manager check if
+/// the source was already initialized. The `next_id` counter is copied
+/// so that cloned clients continue with monotonically increasing IDs.
 impl Clone for McpClient {
     fn clone(&self) -> Self {
         Self {
@@ -484,7 +505,7 @@ impl Clone for McpClient {
             user_id: self.user_id.clone(),
             server_config: self.server_config.clone(),
             custom_headers: self.custom_headers.clone(),
-            initialized: AtomicBool::new(self.initialized.load(Ordering::Relaxed)),
+            initialized: tokio::sync::OnceCell::new(),
         }
     }
 }
@@ -707,7 +728,7 @@ mod tests {
         headers.insert("X-Custom".to_string(), "value".to_string());
 
         let config = McpServerConfig::new("test", "http://localhost:8080").with_headers(headers);
-        let client = McpClient::new_with_config(config.clone());
+        let client = McpClient::new_with_config(config.clone()).expect("HTTP config should work");
 
         assert_eq!(client.server_name(), "test");
         assert_eq!(client.server_url(), "http://localhost:8080");
@@ -719,7 +740,7 @@ mod tests {
     #[test]
     fn test_new_with_config_no_headers() {
         let config = McpServerConfig::new("bare", "http://localhost:9090");
-        let client = McpClient::new_with_config(config);
+        let client = McpClient::new_with_config(config).expect("HTTP config should work");
 
         assert_eq!(client.server_name(), "bare");
         assert!(client.custom_headers.is_empty());
@@ -971,4 +992,125 @@ mod tests {
         assert_eq!(obj.len(), 1);
         assert!(obj["outer"]["inner"].is_null());
     }
+
+    // --- Issue 1 regression: new_with_config rejects non-HTTP transport ---
+
+    #[test]
+    fn test_new_with_config_rejects_stdio_transport() {
+        let config = McpServerConfig::new_stdio(
+            "stdio-server",
+            "echo",
+            vec!["hello".to_string()],
+            HashMap::new(),
+        );
+        let result = McpClient::new_with_config(config);
+        let err = result
+            .err()
+            .expect("stdio config must be rejected")
+            .to_string();
+        assert!(
+            err.contains("new_with_config only supports HTTP"),
+            "error should explain the restriction: {}",
+            err
+        );
+    }
+
+    // --- Issue 13: McpToolWrapper unit tests ---
+
+    fn make_test_mcp_tool(destructive: bool) -> McpTool {
+        use crate::tools::mcp::protocol::McpToolAnnotations;
+        McpTool {
+            name: "do_thing".to_string(),
+            description: "Does a thing".to_string(),
+            input_schema: serde_json::json!({
+                "type": "object",
+                "properties": {
+                    "input": {"type": "string"}
+                }
+            }),
+            annotations: if destructive {
+                Some(McpToolAnnotations {
+                    destructive_hint: true,
+                    side_effects_hint: false,
+                    read_only_hint: false,
+                    execution_time_hint: None,
+                })
+            } else {
+                None
+            },
+        }
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_name_is_prefixed() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(false),
+            prefixed_name: "mcp__myserver__do_thing".to_string(),
+            client,
+        };
+        assert_eq!(wrapper.name(), "mcp__myserver__do_thing");
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_description() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(false),
+            prefixed_name: "mcp__s__do_thing".to_string(),
+            client,
+        };
+        assert_eq!(wrapper.description(), "Does a thing");
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_parameters_schema() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(false),
+            prefixed_name: "mcp__s__do_thing".to_string(),
+            client,
+        };
+        let schema = wrapper.parameters_schema();
+        assert_eq!(schema["type"], "object");
+        assert!(schema["properties"]["input"].is_object());
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_requires_sanitization() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(false),
+            prefixed_name: "mcp__s__do_thing".to_string(),
+            client,
+        };
+        assert!(
+            wrapper.requires_sanitization(),
+            "MCP tools should always require sanitization"
+        );
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_approval_destructive() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(true),
+            prefixed_name: "mcp__s__do_thing".to_string(),
+            client,
+        };
+        let approval = wrapper.requires_approval(&serde_json::json!({}));
+        assert_eq!(approval, ApprovalRequirement::UnlessAutoApproved);
+    }
+
+    #[test]
+    fn test_mcp_tool_wrapper_approval_non_destructive() {
+        let client = Arc::new(McpClient::new("http://localhost:8080"));
+        let wrapper = McpToolWrapper {
+            tool: make_test_mcp_tool(false),
+            prefixed_name: "mcp__s__do_thing".to_string(),
+            client,
+        };
+        let approval = wrapper.requires_approval(&serde_json::json!({}));
+        assert_eq!(approval, ApprovalRequirement::Never);
+    }
 }

src/tools/mcp/config.rs

@@ -163,10 +163,8 @@ impl McpServerConfig {
                 }
 
                 // Remote servers must use HTTPS (localhost is allowed for development)
-                let url_lower = self.url.to_lowercase();
+                let is_localhost = is_localhost_url(&self.url);
-                let is_localhost =
+                if !is_localhost && !self.url.to_lowercase().starts_with("https://") {
-                    url_lower.contains("localhost") || url_lower.contains("127.0.0.1");
-                if !is_localhost && !url_lower.starts_with("https://") {
                     return Err(ConfigError::InvalidConfig {
                         reason: "Remote MCP servers must use HTTPS".to_string(),
                     });
@@ -442,7 +440,12 @@ pub async fn save_mcp_servers_to(
     }
 
     let content = serde_json::to_string_pretty(config)?;
-    fs::write(path, content).await?;
+
+    // Write to a temporary file first, then atomically rename to avoid
+    // corrupting the config if the process crashes during the write.
+    let tmp_path = path.with_extension("json.tmp");
+    fs::write(&tmp_path, content).await?;
+    fs::rename(&tmp_path, path).await?;
 
     Ok(())
 }
@@ -570,7 +573,7 @@ pub async fn remove_mcp_server_db(
 ///
 /// Uses `url::Url` for proper parsing so edge cases (IPv6, userinfo, ports)
 /// are handled correctly without manual string splitting.
-fn is_localhost_url(url: &str) -> bool {
+pub(crate) fn is_localhost_url(url: &str) -> bool {
     let Ok(parsed) = url::Url::parse(url) else {
         return false;
     };
@@ -1125,4 +1128,33 @@ mod tests {
         assert!(parsed.transport.is_none());
         assert_eq!(parsed.headers.get("X-Custom").unwrap(), "value");
     }
+
+    // --- Issue 3 regression: is_localhost_url rejects attacker subdomains ---
+
+    #[test]
+    fn test_is_localhost_url_rejects_attacker_subdomain() {
+        // Before the fix, url.contains("localhost") matched this.
+        assert!(
+            !is_localhost_url("http://evil.localhost.attacker.com:8080/mcp"),
+            "attacker subdomain containing 'localhost' must not be treated as local"
+        );
+    }
+
+    #[test]
+    fn test_is_localhost_url_accepts_real_localhost() {
+        assert!(is_localhost_url("http://localhost:8080/mcp"));
+        assert!(is_localhost_url("https://localhost/path"));
+    }
+
+    #[test]
+    fn test_is_localhost_url_accepts_loopback_ip() {
+        assert!(is_localhost_url("http://127.0.0.1:3000"));
+        assert!(is_localhost_url("http://[::1]:3000"));
+    }
+
+    #[test]
+    fn test_is_localhost_url_rejects_remote() {
+        assert!(!is_localhost_url("https://mcp.example.com"));
+        assert!(!is_localhost_url("http://192.168.1.1:8080"));
+    }
 }

src/tools/mcp/factory.rs

@@ -18,6 +18,8 @@ pub enum McpFactoryError {
     UnixConnect { name: String, reason: String },
     #[error("Unix socket transport is not supported on this platform (server '{name}')")]
     UnixNotSupported { name: String },
+    #[error("Invalid configuration for MCP server '{name}': {reason}")]
+    InvalidConfig { name: String, reason: String },
 }
 
 /// Create an `McpClient` from a server configuration, dispatching on the
@@ -89,10 +91,18 @@ pub async fn create_client_from_config(
                     ))
                 } else {
                     Ok(McpClient::new_with_config(server)
+                        .map_err(|e| McpFactoryError::InvalidConfig {
+                            name: server_name.clone(),
+                            reason: e.to_string(),
+                        })?
                         .with_session_manager(Arc::clone(session_manager)))
                 }
             } else {
                 Ok(McpClient::new_with_config(server)
+                    .map_err(|e| McpFactoryError::InvalidConfig {
+                        name: server_name,
+                        reason: e.to_string(),
+                    })?
                     .with_session_manager(Arc::clone(session_manager)))
             }
         }

src/tools/mcp/http_transport.rs

@@ -139,7 +139,7 @@ impl McpTransport for HttpMcpTransport {
             .to_string();
 
         if content_type.contains("text/event-stream") {
-            self.parse_sse_response(response).await
+            self.parse_sse_response(response, request.id).await
         } else {
             response.json().await.map_err(|e| {
                 ToolError::ExternalService(format!(
@@ -161,11 +161,14 @@ impl McpTransport for HttpMcpTransport {
 }
 
 impl HttpMcpTransport {
-    /// Parse a Server-Sent Events response, returning the first valid JSON-RPC
+    /// Parse a Server-Sent Events response, returning the JSON-RPC response
-    /// `data:` line as an [`McpResponse`].
+    /// whose `id` matches `request_id`. Non-matching events (e.g. server
+    /// notifications or progress updates) are skipped so that the caller
+    /// receives the actual result for its request.
     async fn parse_sse_response(
         &self,
         response: reqwest::Response,
+        request_id: Option<u64>,
     ) -> Result<McpResponse, ToolError> {
         use futures::StreamExt;
 
@@ -202,9 +205,10 @@ impl HttpMcpTransport {
                     remaining_start = i + 1;
 
                     if let Some(json_str) = line.strip_prefix("data: ")
-                        && let Ok(response) = serde_json::from_str::<McpResponse>(json_str)
+                        && let Ok(resp) = serde_json::from_str::<McpResponse>(json_str)
+                        && resp.id == request_id
                     {
-                        return Ok(response);
+                        return Ok(resp);
                     }
                 }
             }
@@ -216,14 +220,15 @@ impl HttpMcpTransport {
 
         // Process any remaining data without a trailing newline.
         if let Some(json_str) = buffer.strip_prefix("data: ")
-            && let Ok(response) = serde_json::from_str::<McpResponse>(json_str.trim())
+            && let Ok(resp) = serde_json::from_str::<McpResponse>(json_str.trim())
+            && resp.id == request_id
         {
-            return Ok(response);
+            return Ok(resp);
         }
 
         Err(ToolError::ExternalService(format!(
-            "[{}] No valid data in SSE response: {}",
+            "[{}] No matching response (id={:?}) in SSE stream",
-            self.server_name, buffer
+            self.server_name, request_id
         )))
     }
 }

src/tools/mcp/stdio_transport.rs

@@ -14,7 +14,7 @@ use tokio::sync::{Mutex, oneshot};
 use tokio::task::JoinHandle;
 
 use crate::tools::mcp::protocol::{McpRequest, McpResponse};
-use crate::tools::mcp::transport::{McpTransport, spawn_jsonrpc_reader, write_jsonrpc_line};
+use crate::tools::mcp::transport::{McpTransport, spawn_jsonrpc_reader, stream_transport_send};
 use crate::tools::tool::ToolError;
 
 /// MCP transport that communicates with a child process over stdin/stdout.
@@ -118,63 +118,14 @@ impl McpTransport for StdioMcpTransport {
         request: &McpRequest,
         _headers: &HashMap<String, String>,
     ) -> Result<McpResponse, ToolError> {
-        // JSON-RPC notifications (no id) are fire-and-forget: the server
+        stream_transport_send(
-        // will not send a response, so we must not wait for one.
+            &self.stdin,
-        if request.id.is_none() {
+            &self.pending,
-            let mut stdin = self.stdin.lock().await;
+            request,
-            write_jsonrpc_line(&mut *stdin, request).await?;
+            &self.server_name,
-            return Ok(McpResponse {
+            Duration::from_secs(30),
-                jsonrpc: "2.0".to_string(),
+        )
-                id: None,
+        .await
-                result: None,
-                error: None,
-            });
-        }
-
-        let id = request.id.unwrap_or(0);
-        let (tx, rx) = oneshot::channel();
-
-        // Register the pending response handler before writing the request,
-        // so we don't miss a fast response from the child.
-        {
-            let mut pending = self.pending.lock().await;
-            pending.insert(id, tx);
-        }
-
-        // Write the request to stdin.
-        {
-            let mut stdin = self.stdin.lock().await;
-            if let Err(e) = write_jsonrpc_line(&mut *stdin, request).await {
-                // Remove the pending entry on write failure.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                return Err(e);
-            }
-        }
-
-        // Wait for the response with a timeout.
-        let timeout = Duration::from_secs(30);
-        match tokio::time::timeout(timeout, rx).await {
-            Ok(Ok(response)) => Ok(response),
-            Ok(Err(_)) => {
-                // Sender was dropped (reader task ended). Clean up pending entry.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                Err(ToolError::ExternalService(format!(
-                    "[{}] MCP server closed connection before responding to request {:?}",
-                    self.server_name, request.id
-                )))
-            }
-            Err(_) => {
-                // Timeout: remove the pending entry.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                Err(ToolError::ExternalService(format!(
-                    "[{}] Timeout waiting for response to request {:?} after {:?}",
-                    self.server_name, request.id, timeout
-                )))
-            }
-        }
     }
 
     async fn shutdown(&self) -> Result<(), ToolError> {

src/tools/mcp/transport.rs

@@ -97,7 +97,13 @@ pub fn spawn_jsonrpc_reader<R: AsyncBufRead + Unpin + Send + 'static>(
                 }
             };
 
-            let id = response.id.unwrap_or(0);
+            let Some(id) = response.id else {
+                tracing::debug!(
+                    "[{}] Received JSON-RPC notification (no id), skipping dispatch",
+                    server_name
+                );
+                continue;
+            };
             let mut map = pending.lock().await;
             if let Some(tx) = map.remove(&id) {
                 // Ignore send error — the receiver may have been dropped (timeout).
@@ -115,6 +121,76 @@ pub fn spawn_jsonrpc_reader<R: AsyncBufRead + Unpin + Send + 'static>(
     })
 }
 
+/// Send a JSON-RPC request over a stream-based transport (stdio / unix socket).
+///
+/// Handles notification fire-and-forget, pending response registration,
+/// write, timeout, and cleanup. Used by both [`StdioMcpTransport`] and
+/// [`UnixMcpTransport`] to avoid duplicating the send logic.
+pub(crate) async fn stream_transport_send<W: AsyncWrite + Unpin>(
+    writer: &Mutex<W>,
+    pending: &Mutex<HashMap<u64, oneshot::Sender<McpResponse>>>,
+    request: &McpRequest,
+    server_name: &str,
+    timeout_duration: std::time::Duration,
+) -> Result<McpResponse, ToolError> {
+    // JSON-RPC notifications (no id) are fire-and-forget: the server
+    // will not send a response, so we must not wait for one.
+    if request.id.is_none() {
+        let mut w = writer.lock().await;
+        write_jsonrpc_line(&mut *w, request).await?;
+        return Ok(McpResponse {
+            jsonrpc: "2.0".to_string(),
+            id: None,
+            result: None,
+            error: None,
+        });
+    }
+
+    let id = request.id.unwrap_or(0);
+    let (tx, rx) = oneshot::channel();
+
+    // Register the pending response handler before writing the request,
+    // so we don't miss a fast response from the server.
+    {
+        let mut map = pending.lock().await;
+        map.insert(id, tx);
+    }
+
+    // Write the request.
+    {
+        let mut w = writer.lock().await;
+        if let Err(e) = write_jsonrpc_line(&mut *w, request).await {
+            // Remove the pending entry on write failure.
+            let mut map = pending.lock().await;
+            map.remove(&id);
+            return Err(e);
+        }
+    }
+
+    // Wait for the response with a timeout.
+    match tokio::time::timeout(timeout_duration, rx).await {
+        Ok(Ok(response)) => Ok(response),
+        Ok(Err(_)) => {
+            // Sender was dropped (reader task ended). Clean up pending entry.
+            let mut map = pending.lock().await;
+            map.remove(&id);
+            Err(ToolError::ExternalService(format!(
+                "[{}] MCP server closed connection before responding to request {:?}",
+                server_name, request.id
+            )))
+        }
+        Err(_) => {
+            // Timeout: remove the pending entry.
+            let mut map = pending.lock().await;
+            map.remove(&id);
+            Err(ToolError::ExternalService(format!(
+                "[{}] Timeout waiting for response to request {:?} after {:?}",
+                server_name, request.id, timeout_duration
+            )))
+        }
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -193,4 +269,32 @@ mod tests {
 
         handle.await.expect("reader task should finish");
     }
+
+    /// Issue 9 regression: a JSON-RPC notification (no id) must not resolve
+    /// a pending request keyed by id 0 (the old `unwrap_or(0)` default).
+    #[tokio::test]
+    async fn test_notification_does_not_resolve_pending_id_zero() {
+        // A notification response (no id), followed by a proper response for id 0.
+        let notification = r#"{"jsonrpc":"2.0","method":"notifications/progress","params":{}}"#;
+        let real_response = r#"{"jsonrpc":"2.0","id":0,"result":{"ok":true}}"#;
+        let input = format!("{notification}\n{real_response}\n");
+
+        let reader = std::io::Cursor::new(input.into_bytes());
+        let pending: Arc<Mutex<HashMap<u64, oneshot::Sender<McpResponse>>>> =
+            Arc::new(Mutex::new(HashMap::new()));
+
+        let (tx, rx) = oneshot::channel();
+        {
+            let mut map = pending.lock().await;
+            map.insert(0, tx);
+        }
+
+        let handle = spawn_jsonrpc_reader(reader, pending.clone(), "test".into());
+
+        let resp = rx.await.expect("should receive the real id=0 response");
+        assert_eq!(resp.id, Some(0));
+        assert!(resp.result.is_some());
+
+        handle.await.expect("reader task should finish");
+    }
 }

src/tools/mcp/unix_transport.rs

@@ -15,7 +15,7 @@ use tokio::sync::{Mutex, oneshot};
 use tokio::task::JoinHandle;
 
 use crate::tools::mcp::protocol::{McpRequest, McpResponse};
-use crate::tools::mcp::transport::{McpTransport, spawn_jsonrpc_reader, write_jsonrpc_line};
+use crate::tools::mcp::transport::{McpTransport, spawn_jsonrpc_reader, stream_transport_send};
 use crate::tools::tool::ToolError;
 
 /// MCP transport that communicates over a Unix domain socket.
@@ -91,63 +91,14 @@ impl McpTransport for UnixMcpTransport {
         request: &McpRequest,
         _headers: &HashMap<String, String>,
     ) -> Result<McpResponse, ToolError> {
-        // JSON-RPC notifications (no id) are fire-and-forget: the server
+        stream_transport_send(
-        // will not send a response, so we must not wait for one.
+            &self.writer,
-        if request.id.is_none() {
+            &self.pending,
-            let mut writer = self.writer.lock().await;
+            request,
-            write_jsonrpc_line(&mut *writer, request).await?;
+            &self.server_name,
-            return Ok(McpResponse {
+            Duration::from_secs(30),
-                jsonrpc: "2.0".to_string(),
+        )
-                id: None,
+        .await
-                result: None,
-                error: None,
-            });
-        }
-
-        let id = request.id.unwrap_or(0);
-        let (tx, rx) = oneshot::channel();
-
-        // Register the pending response handler before writing the request,
-        // so we don't miss a fast response from the server.
-        {
-            let mut pending = self.pending.lock().await;
-            pending.insert(id, tx);
-        }
-
-        // Write the request to the socket.
-        {
-            let mut writer = self.writer.lock().await;
-            if let Err(e) = write_jsonrpc_line(&mut *writer, request).await {
-                // Remove the pending entry on write failure.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                return Err(e);
-            }
-        }
-
-        // Wait for the response with a timeout.
-        let timeout = Duration::from_secs(30);
-        match tokio::time::timeout(timeout, rx).await {
-            Ok(Ok(response)) => Ok(response),
-            Ok(Err(_)) => {
-                // Sender was dropped (reader task ended). Clean up pending entry.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                Err(ToolError::ExternalService(format!(
-                    "[{}] MCP server closed connection before responding to request {:?}",
-                    self.server_name, request.id
-                )))
-            }
-            Err(_) => {
-                // Timeout: remove the pending entry.
-                let mut pending = self.pending.lock().await;
-                pending.remove(&id);
-                Err(ToolError::ExternalService(format!(
-                    "[{}] Timeout waiting for response to request {:?} after {:?}",
-                    self.server_name, request.id, timeout
-                )))
-            }
-        }
     }
 
     async fn shutdown(&self) -> Result<(), ToolError> {

src/tools/schema_validator.rs

@@ -558,48 +558,7 @@ mod tests {
             // Routine tools
             (
                 "routine_create",
-                serde_json::json!({
+                crate::tools::builtin::routine::routine_create_parameters_schema(),
-                    "type": "object",
-                    "properties": {
-                        "name": { "type": "string", "description": "Routine name" },
-                        "description": { "type": "string", "description": "What it does" },
-                        "trigger_type": {
-                            "type": "string",
-                            "enum": ["cron", "event", "system_event", "manual"],
-                            "description": "When the routine fires"
-                        },
-                        "schedule": { "type": "string", "description": "Cron expression" },
-                        "event_pattern": { "type": "string", "description": "Regex pattern" },
-                        "event_channel": { "type": "string", "description": "Channel filter" },
-                        "event_source": { "type": "string", "description": "System event source" },
-                        "event_type": { "type": "string", "description": "System event type" },
-                        "event_filters": {
-                            "type": "object",
-                            "additionalProperties": { "type": "string" },
-                            "description": "Exact-match payload filters"
-                        },
-                        "prompt": { "type": "string", "description": "Instructions" },
-                        "context_paths": {
-                            "type": "array",
-                            "items": { "type": "string" },
-                            "description": "Workspace paths to load"
-                        },
-                        "action_type": {
-                            "type": "string",
-                            "enum": ["lightweight", "full_job"],
-                            "description": "Execution mode"
-                        },
-                        "cooldown_secs": { "type": "integer", "description": "Min seconds between fires" },
-                        "tool_permissions": {
-                            "type": "array",
-                            "items": { "type": "string" },
-                            "description": "Pre-authorized tools for full_job mode"
-                        },
-                        "notify_channel": { "type": "string", "description": "Channel for message tool" },
-                        "notify_user": { "type": "string", "description": "User/target to notify" }
-                    },
-                    "required": ["name", "trigger_type", "prompt"]
-                }),
             ),
             (
                 "routine_list",
@@ -611,17 +570,7 @@ mod tests {
             ),
             (
                 "routine_update",
-                serde_json::json!({
+                crate::tools::builtin::routine::routine_update_parameters_schema(),
-                    "type": "object",
-                    "properties": {
-                        "name": { "type": "string", "description": "Name" },
-                        "enabled": { "type": "boolean", "description": "Toggle" },
-                        "prompt": { "type": "string", "description": "New prompt" },
-                        "schedule": { "type": "string", "description": "New cron schedule" },
-                        "description": { "type": "string", "description": "New description" }
-                    },
-                    "required": ["name"]
-                }),
             ),
             (
                 "routine_delete",

src/tools/tool.rs

@@ -430,9 +430,24 @@ pub fn redact_params(params: &serde_json::Value, sensitive: &[&str]) -> serde_js
 /// Properties without a `"type"` field are allowed (freeform/any-type).
 /// This is an intentional pattern used by tools like `json` and `http` for
 /// OpenAI compatibility, since union types with arrays require `items`.
+/// Maximum nesting depth for tool schema validation to prevent stack overflow
+/// on maliciously crafted schemas.
+const MAX_SCHEMA_DEPTH: usize = 16;
+
 pub fn validate_tool_schema(schema: &serde_json::Value, path: &str) -> Vec<String> {
+    validate_tool_schema_inner(schema, path, 0)
+}
+
+fn validate_tool_schema_inner(schema: &serde_json::Value, path: &str, depth: usize) -> Vec<String> {
     let mut errors = Vec::new();
 
+    if depth > MAX_SCHEMA_DEPTH {
+        errors.push(format!(
+            "{path}: schema nesting exceeds maximum depth of {MAX_SCHEMA_DEPTH}"
+        ));
+        return errors;
+    }
+
     // Rule 1: must have "type": "object" at this level
     match schema.get("type").and_then(|t| t.as_str()) {
         Some("object") => {}
@@ -474,14 +489,17 @@ pub fn validate_tool_schema(schema: &serde_json::Value, path: &str) -> Vec<Strin
         if let Some(prop_type) = prop.get("type").and_then(|t| t.as_str()) {
             match prop_type {
                 "object" => {
-                    errors.extend(validate_tool_schema(prop, &prop_path));
+                    errors.extend(validate_tool_schema_inner(prop, &prop_path, depth + 1));
                 }
                 "array" => {
                     if let Some(items) = prop.get("items") {
                         // If items is an object type, recurse
                         if items.get("type").and_then(|t| t.as_str()) == Some("object") {
-                            errors
+                            errors.extend(validate_tool_schema_inner(
-                                .extend(validate_tool_schema(items, &format!("{prop_path}.items")));
+                                items,
+                                &format!("{prop_path}.items"),
+                                depth + 1,
+                            ));
                         }
                     } else {
                         errors.push(format!("{prop_path}: array property missing \"items\""));
@@ -810,6 +828,33 @@ mod tests {
         assert!(errors[0].contains("\"missing_field\""));
     }
 
+    /// Regression test for issue #975: deeply nested schemas must not cause
+    /// stack overflow. The validator should stop at MAX_SCHEMA_DEPTH and
+    /// report an error instead of recursing infinitely.
+    #[test]
+    fn test_validate_schema_depth_limit() {
+        // Build a schema nested 20 levels deep (exceeds MAX_SCHEMA_DEPTH=16)
+        let mut schema = serde_json::json!({
+            "type": "object",
+            "properties": {
+                "leaf": { "type": "string" }
+            }
+        });
+        for _ in 0..20 {
+            schema = serde_json::json!({
+                "type": "object",
+                "properties": {
+                    "nested": schema
+                }
+            });
+        }
+        let errors = validate_tool_schema(&schema, "test");
+        assert!(
+            errors.iter().any(|e| e.contains("maximum depth")),
+            "expected depth limit error, got: {errors:?}"
+        );
+    }
+
     #[test]
     fn test_approval_context_autonomous_allows_unless_auto_approved() {
         let ctx = ApprovalContext::autonomous();

src/tools/wasm/capabilities_schema.rs

@@ -101,24 +101,75 @@ pub struct CapabilitiesFile {
     pub capabilities: Option<Box<CapabilitiesFile>>,
 }
 
+/// Maximum length for the description field to prevent memory abuse.
+const MAX_DESCRIPTION_CHARS: usize = 4096;
+/// Maximum serialized size of the parameters schema JSON.
+const MAX_PARAMETERS_SCHEMA_BYTES: usize = 64 * 1024;
+
 impl CapabilitiesFile {
     /// Parse from JSON string.
     pub fn from_json(json: &str) -> Result<Self, serde_json::Error> {
-        serde_json::from_str::<Self>(json).map(Self::resolve_nested)
+        let mut caps = serde_json::from_str::<Self>(json).map(Self::resolve_nested)?;
+        caps.enforce_limits();
+        Ok(caps)
     }
 
     /// Parse from JSON bytes.
     pub fn from_bytes(bytes: &[u8]) -> Result<Self, serde_json::Error> {
-        serde_json::from_slice::<Self>(bytes).map(Self::resolve_nested)
+        let mut caps = serde_json::from_slice::<Self>(bytes).map(Self::resolve_nested)?;
+        caps.enforce_limits();
+        Ok(caps)
+    }
+
+    /// Truncate oversized fields to prevent unbounded memory usage.
+    fn enforce_limits(&mut self) {
+        // Truncate oversized description (issue #976)
+        if let Some(ref desc) = self.description
+            && desc.len() > MAX_DESCRIPTION_CHARS
+        {
+            let truncated = &desc[..desc.floor_char_boundary(MAX_DESCRIPTION_CHARS)];
+            tracing::warn!(
+                "Capabilities description truncated from {} to {} chars",
+                desc.len(),
+                MAX_DESCRIPTION_CHARS,
+            );
+            self.description = Some(truncated.to_string());
+        }
+        // Drop oversized parameters schema (issue #977)
+        if let Some(ref params) = self.parameters {
+            let size = params.to_string().len();
+            if size > MAX_PARAMETERS_SCHEMA_BYTES {
+                tracing::warn!(
+                    "Capabilities parameters schema dropped ({} bytes exceeds {} limit)",
+                    size,
+                    MAX_PARAMETERS_SCHEMA_BYTES,
+                );
+                self.parameters = None;
+            }
+        }
     }
 
     /// Merge nested `capabilities` wrapper into top-level fields.
     ///
     /// Channel-level JSON nests tool capabilities under `"capabilities"`.
     /// This promotes the inner fields so callers can access them uniformly.
-    fn resolve_nested(mut self) -> Self {
+    /// Maximum nesting depth for capabilities resolution.
+    const MAX_NESTED_DEPTH: usize = 8;
+
+    fn resolve_nested(self) -> Self {
+        self.resolve_nested_inner(0)
+    }
+
+    fn resolve_nested_inner(mut self, depth: usize) -> Self {
+        if depth > Self::MAX_NESTED_DEPTH {
+            tracing::warn!(
+                "Capabilities nesting exceeds maximum depth of {}, stopping resolution",
+                Self::MAX_NESTED_DEPTH
+            );
+            return self;
+        }
         if let Some(inner) = self.capabilities.take() {
-            let inner = inner.resolve_nested();
+            let inner = inner.resolve_nested_inner(depth + 1);
             self.description = self.description.or(inner.description);
             self.parameters = self.parameters.or(inner.parameters);
             self.http = self.http.or(inner.http);
@@ -1383,4 +1434,63 @@ mod tests {
             "Outer description should take precedence over inner"
         );
     }
+
+    /// Regression test for issue #974: deeply nested capabilities wrappers
+    /// must not cause stack overflow. resolve_nested should stop at
+    /// MAX_NESTED_DEPTH and return gracefully.
+    #[test]
+    fn test_resolve_nested_depth_limit() {
+        // Build a capabilities file nested beyond MAX_NESTED_DEPTH (8).
+        // The description is at the innermost level which is beyond the limit,
+        // so it won't be resolved — the key assertion is no stack overflow.
+        let mut json = r#"{ "description": "leaf" }"#.to_string();
+        for _ in 0..20 {
+            json = format!(r#"{{ "capabilities": {json} }}"#);
+        }
+        // Should not stack overflow — this is the primary assertion.
+        let _caps = CapabilitiesFile::from_json(&json).unwrap();
+    }
+
+    /// Regression test for issue #976: oversized description strings are truncated.
+    #[test]
+    fn test_description_truncated_at_limit() {
+        let long_desc = "x".repeat(10_000);
+        let json = format!(r#"{{ "description": "{long_desc}" }}"#);
+        let caps = CapabilitiesFile::from_json(&json).unwrap();
+        let desc = caps.description.unwrap();
+        assert!(
+            desc.len() <= super::MAX_DESCRIPTION_CHARS + 50, // allow for minor overhead
+            "description should be truncated to ~{} chars, got {}",
+            super::MAX_DESCRIPTION_CHARS,
+            desc.len()
+        );
+    }
+
+    /// Regression test for issue #977: oversized parameters schema is dropped.
+    #[test]
+    fn test_oversized_parameters_schema_dropped() {
+        // Build a parameters schema larger than MAX_PARAMETERS_SCHEMA_BYTES
+        let mut properties = serde_json::Map::new();
+        for i in 0..2000 {
+            properties.insert(
+                format!("field_{i}"),
+                serde_json::json!({
+                    "type": "string",
+                    "description": "x".repeat(50)
+                }),
+            );
+        }
+        let schema = serde_json::json!({
+            "type": "object",
+            "properties": properties,
+        });
+        let json = serde_json::json!({
+            "parameters": schema,
+        });
+        let caps = CapabilitiesFile::from_json(&json.to_string()).unwrap();
+        assert!(
+            caps.parameters.is_none(),
+            "oversized parameters schema should be dropped"
+        );
+    }
 }

src/worker/job.rs

@@ -1108,9 +1108,10 @@ impl<'a> LoopDelegate for JobDelegate<'a> {
             return LoopSignal::InjectMessage(content);
         }
 
-        // Check for terminal or non-progressing state. The loop should stop when the
+        // Check for terminal or post-completion state. The loop should stop when the
-        // job has been cancelled, failed, stuck, or already completed — not just the
+        // job has been cancelled, failed, or already completed — but NOT when Stuck,
-        // three states that `is_terminal()` covers (Accepted/Failed/Cancelled).
+        // because Stuck is recoverable (Stuck -> InProgress via self-repair).
+        // Stopping on Stuck would prevent recovery from resuming the worker (issue #892).
         if let Ok(ctx) = self
             .worker
             .context_manager()
@@ -1120,7 +1121,6 @@ impl<'a> LoopDelegate for JobDelegate<'a> {
                 ctx.state,
                 JobState::Cancelled
                     | JobState::Failed
-                    | JobState::Stuck
                     | JobState::Completed
                     | JobState::Submitted
                     | JobState::Accepted

tests/e2e_advanced_traces.rs

@@ -9,6 +9,10 @@ mod support;
 mod advanced {
     use std::time::Duration;
 
+    use ironclaw::agent::routine::Trigger;
+    use ironclaw::channels::IncomingMessage;
+    use ironclaw::db::Database;
+
     use crate::support::cleanup::CleanupGuard;
     use crate::support::test_rig::TestRigBuilder;
     use crate::support::trace_llm::LlmTrace;
@@ -19,6 +23,28 @@ mod advanced {
     );
     const TIMEOUT: Duration = Duration::from_secs(30);
 
+    async fn wait_for_routine_run(
+        db: &std::sync::Arc<dyn Database>,
+        routine_id: uuid::Uuid,
+        timeout: Duration,
+    ) -> Vec<ironclaw::agent::routine::RoutineRun> {
+        let deadline = tokio::time::Instant::now() + timeout;
+        loop {
+            let runs = db
+                .list_routine_runs(routine_id, 10)
+                .await
+                .expect("list_routine_runs");
+            if !runs.is_empty() {
+                return runs;
+            }
+            assert!(
+                tokio::time::Instant::now() < deadline,
+                "timed out waiting for routine run"
+            );
+            tokio::time::sleep(Duration::from_millis(100)).await;
+        }
+    }
+
     // -----------------------------------------------------------------------
     // 1. Multi-turn memory coherence
     // -----------------------------------------------------------------------
@@ -380,6 +406,118 @@ mod advanced {
         rig.shutdown();
     }
 
+    // -----------------------------------------------------------------------
+    // 6b. Event routine: Telegram-scoped trigger fires on matching message
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn routine_event_trigger_telegram_channel_fires() {
+        let trace = LlmTrace::from_file(format!("{FIXTURES}/routine_event_telegram.json")).unwrap();
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_routines()
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message(
+            "Create a routine that watches Telegram messages starting with 'bug:' and alerts me.",
+        )
+        .await;
+        let create_responses = rig.wait_for_responses(1, TIMEOUT).await;
+        rig.verify_trace_expects(&trace, &create_responses);
+
+        let routine = rig
+            .database()
+            .get_routine_by_name("test-user", "telegram-bug-watcher")
+            .await
+            .expect("get_routine_by_name")
+            .expect("telegram-bug-watcher should exist");
+
+        match &routine.trigger {
+            Trigger::Event { channel, pattern } => {
+                assert_eq!(channel.as_deref(), Some("telegram"));
+                assert_eq!(pattern, "^bug\\b");
+            }
+            other => panic!("expected event trigger, got {other:?}"),
+        }
+
+        rig.send_incoming(IncomingMessage::new(
+            "telegram",
+            "test-user",
+            "bug: home button broken",
+        ))
+        .await;
+
+        let runs = wait_for_routine_run(rig.database(), routine.id, TIMEOUT).await;
+        assert_eq!(runs[0].trigger_type, "event");
+
+        let responses = rig.wait_for_responses(3, TIMEOUT).await;
+        assert!(
+            responses.iter().any(|response| {
+                response
+                    .metadata
+                    .get("source")
+                    .and_then(|value| value.as_str())
+                    == Some("routine")
+                    && response.content.contains("telegram-bug-watcher")
+                    && response.content.contains("Bug report detected")
+            }),
+            "expected routine notification in responses: {responses:?}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // 6c. Event routine without channel filter still fires on Telegram
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn routine_event_trigger_without_channel_filter_still_fires() {
+        let trace =
+            LlmTrace::from_file(format!("{FIXTURES}/routine_event_any_channel.json")).unwrap();
+        let rig = TestRigBuilder::new()
+            .with_trace(trace)
+            .with_routines()
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message(
+            "Create a routine that watches messages starting with 'bug:' and alerts me.",
+        )
+        .await;
+        let _ = rig.wait_for_responses(1, TIMEOUT).await;
+
+        let routine = rig
+            .database()
+            .get_routine_by_name("test-user", "any-channel-bug-watcher")
+            .await
+            .expect("get_routine_by_name")
+            .expect("any-channel-bug-watcher should exist");
+
+        match &routine.trigger {
+            Trigger::Event { channel, pattern } => {
+                assert_eq!(channel, &None);
+                assert_eq!(pattern, "^bug\\b");
+            }
+            other => panic!("expected event trigger, got {other:?}"),
+        }
+
+        rig.send_incoming(IncomingMessage::new(
+            "telegram",
+            "test-user",
+            "bug: login button broken",
+        ))
+        .await;
+
+        let runs = wait_for_routine_run(rig.database(), routine.id, TIMEOUT).await;
+        assert_eq!(runs[0].trigger_type, "event");
+
+        rig.shutdown();
+    }
+
     // -----------------------------------------------------------------------
     // 7. Prompt injection resilience
     // -----------------------------------------------------------------------

tests/e2e_builtin_tool_coverage.rs

@@ -10,6 +10,8 @@ mod support;
 mod tests {
     use std::time::Duration;
 
+    use ironclaw::agent::routine::{RoutineAction, Trigger};
+
     use crate::support::test_rig::TestRigBuilder;
     use crate::support::trace_llm::LlmTrace;
 
@@ -123,6 +125,39 @@ mod tests {
             "routine_list should succeed: {completed:?}"
         );
 
+        let routine = rig
+            .database()
+            .get_routine_by_name("test-user", "daily-check")
+            .await
+            .expect("get_routine_by_name")
+            .expect("daily-check should exist");
+
+        match &routine.trigger {
+            Trigger::Cron { schedule, timezone } => {
+                assert_eq!(schedule, "0 0 9 * * *");
+                assert_eq!(timezone.as_deref(), Some("America/New_York"));
+            }
+            other => panic!("expected cron trigger, got {other:?}"),
+        }
+
+        match &routine.action {
+            RoutineAction::Lightweight {
+                context_paths,
+                use_tools,
+                max_tool_rounds,
+                ..
+            } => {
+                assert_eq!(context_paths, &vec!["context/priorities.md".to_string()]);
+                assert!(*use_tools, "lightweight routine should keep use_tools=true");
+                assert_eq!(*max_tool_rounds, 2);
+            }
+            other => panic!("expected lightweight action, got {other:?}"),
+        }
+
+        assert_eq!(routine.notify.channel.as_deref(), Some("telegram"));
+        assert_eq!(routine.notify.user, "ops-team");
+        assert_eq!(routine.guardrails.cooldown.as_secs(), 600);
+
         rig.shutdown();
     }
 
@@ -168,7 +203,48 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 5: routine_history
+    // Test 5: routine_manual_create
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn routine_manual_create() {
+        let trace = LlmTrace::from_file(concat!(
+            env!("CARGO_MANIFEST_DIR"),
+            "/tests/fixtures/llm_traces/tools/routine_manual_create.json"
+        ))
+        .expect("failed to load routine_manual_create.json");
+
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message("Create a manual routine for bug triage")
+            .await;
+        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
+
+        rig.verify_trace_expects(&trace, &responses);
+
+        let routine = rig
+            .database()
+            .get_routine_by_name("test-user", "manual-triage")
+            .await
+            .expect("get_routine_by_name")
+            .expect("manual-triage should exist");
+
+        assert!(matches!(routine.trigger, Trigger::Manual));
+        assert!(
+            matches!(&routine.action, RoutineAction::Lightweight { use_tools, .. } if !*use_tools),
+            "manual routine should default to lightweight without tools: {:?}",
+            routine.action
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 6: routine_history
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -205,7 +281,7 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 6: routine_system_event_emit
+    // Test 7: routine_system_event_emit
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -253,11 +329,47 @@ mod tests {
             emit_result.1
         );
 
+        let routine = rig
+            .database()
+            .get_routine_by_name("test-user", "gh-issue-emit-test")
+            .await
+            .expect("get_routine_by_name")
+            .expect("gh-issue-emit-test should exist");
+
+        match &routine.trigger {
+            Trigger::SystemEvent {
+                source,
+                event_type,
+                filters,
+            } => {
+                assert_eq!(source, "github");
+                assert_eq!(event_type, "issue.opened");
+                assert_eq!(
+                    filters.get("repository").map(String::as_str),
+                    Some("nearai/ironclaw")
+                );
+                assert_eq!(filters.get("priority").map(String::as_str), Some("p1"));
+            }
+            other => panic!("expected system_event trigger, got {other:?}"),
+        }
+
+        match &routine.action {
+            RoutineAction::FullJob {
+                description,
+                tool_permissions,
+                ..
+            } => {
+                assert!(description.contains("Summarize the new issue"));
+                assert_eq!(tool_permissions, &vec!["shell".to_string()]);
+            }
+            other => panic!("expected full_job action, got {other:?}"),
+        }
+
         rig.shutdown();
     }
 
     // -----------------------------------------------------------------------
-    // Test 7: skill_install_routine_webhook_sim
+    // Test 8: skill_install_routine_webhook_sim
     // -----------------------------------------------------------------------
 
     #[tokio::test]

tests/fixtures/llm_traces/advanced/routine_event_any_channel.json

@@ -0,0 +1,54 @@
+{
+  "model_name": "advanced-routine-event-any-channel",
+  "expects": {
+    "tools_used": ["routine_create"],
+    "all_tools_succeeded": true,
+    "min_responses": 1
+  },
+  "steps": [
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_routine_create_event_any_channel",
+            "name": "routine_create",
+            "arguments": {
+              "name": "any-channel-bug-watcher",
+              "description": "Watch bug reports from any incoming channel.",
+              "trigger_type": "event",
+              "event_pattern": "^bug\\b",
+              "prompt": "Summarize the bug report in one line."
+            }
+          }
+        ],
+        "input_tokens": 130,
+        "output_tokens": 38
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "Created the any-channel-bug-watcher routine for bug messages.",
+        "input_tokens": 170,
+        "output_tokens": 18
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "I saw the Telegram message.",
+        "input_tokens": 90,
+        "output_tokens": 12
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "Bug report detected: login button broken.",
+        "input_tokens": 120,
+        "output_tokens": 14
+      }
+    }
+  ]
+}

tests/fixtures/llm_traces/advanced/routine_event_telegram.json

@@ -0,0 +1,55 @@
+{
+  "model_name": "advanced-routine-event-telegram",
+  "expects": {
+    "tools_used": ["routine_create"],
+    "all_tools_succeeded": true,
+    "min_responses": 1
+  },
+  "steps": [
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_routine_create_event_telegram",
+            "name": "routine_create",
+            "arguments": {
+              "name": "telegram-bug-watcher",
+              "description": "Watch Telegram bug reports and alert on them.",
+              "trigger_type": "event",
+              "event_channel": "telegram",
+              "event_pattern": "^bug\\b",
+              "prompt": "Summarize the bug report in one line."
+            }
+          }
+        ],
+        "input_tokens": 140,
+        "output_tokens": 40
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "Created the telegram-bug-watcher routine for Telegram bug messages.",
+        "input_tokens": 180,
+        "output_tokens": 20
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "I saw the Telegram message.",
+        "input_tokens": 90,
+        "output_tokens": 12
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "Bug report detected: home button broken.",
+        "input_tokens": 120,
+        "output_tokens": 14
+      }
+    }
+  ]
+}

tests/fixtures/llm_traces/tools/routine_create_list.json

@@ -18,8 +18,16 @@
               "name": "daily-check",
               "trigger_type": "cron",
               "schedule": "0 0 9 * * *",
+              "timezone": "America/New_York",
               "prompt": "Check system status and report any issues.",
-              "description": "Daily system health check"
+              "description": "Daily system health check",
+              "context_paths": ["context/priorities.md"],
+              "action_type": "lightweight",
+              "use_tools": true,
+              "max_tool_rounds": 2,
+              "cooldown_secs": 600,
+              "notify_channel": "telegram",
+              "notify_user": "ops-team"
             }
           }
         ],

tests/fixtures/llm_traces/tools/routine_manual_create.json

@@ -0,0 +1,36 @@
+{
+  "model_name": "test-routine-manual-create",
+  "expects": {
+    "tools_used": ["routine_create"],
+    "all_tools_succeeded": true,
+    "min_responses": 1
+  },
+  "steps": [
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_rc_manual_1",
+            "name": "routine_create",
+            "arguments": {
+              "name": "manual-triage",
+              "trigger_type": "manual",
+              "prompt": "Summarize the latest bug reports when this routine is fired."
+            }
+          }
+        ],
+        "input_tokens": 90,
+        "output_tokens": 22
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "Created the manual-triage routine. It will only run when explicitly fired.",
+        "input_tokens": 140,
+        "output_tokens": 18
+      }
+    }
+  ]
+}

tests/fixtures/llm_traces/tools/routine_system_event_emit.json

@@ -21,7 +21,12 @@
               "trigger_type": "system_event",
               "event_source": "github",
               "event_type": "issue.opened",
+              "event_filters": {
+                "repository": "nearai/ironclaw",
+                "priority": "p1"
+              },
               "action_type": "full_job",
+              "tool_permissions": ["shell"],
               "prompt": "Summarize the new issue and propose next steps."
             }
           }
@@ -42,6 +47,7 @@
               "event_type": "issue.opened",
               "payload": {
                 "repository": "nearai/ironclaw",
+                "priority": "p1",
                 "issue_number": 123,
                 "title": "Support event-driven project workflow"
               }