Update files

packages/server/src/server/agent/agent-manager.ts

@@ -1171,10 +1171,33 @@ export class AgentManager {
         break;
       case "turn_failed":
         agent.lastError = event.error;
+        for (const [requestId] of agent.pendingPermissions) {
+          agent.pendingPermissions.delete(requestId);
+          if (!options?.fromHistory) {
+            this.dispatchStream(agent.id, {
+              type: "permission_resolved",
+              provider: event.provider,
+              requestId,
+              resolution: { behavior: "deny", message: "Turn failed" },
+            });
+          }
+        }
+        this.emitState(agent);
         break;
       case "turn_canceled":
-        // Cancellation is not an error, just clear any previous error
         agent.lastError = undefined;
+        for (const [requestId] of agent.pendingPermissions) {
+          agent.pendingPermissions.delete(requestId);
+          if (!options?.fromHistory) {
+            this.dispatchStream(agent.id, {
+              type: "permission_resolved",
+              provider: event.provider,
+              requestId,
+              resolution: { behavior: "deny", message: "Interrupted" },
+            });
+          }
+        }
+        this.emitState(agent);
         break;
       case "permission_requested":
         agent.pendingPermissions.set(event.request.id, event.request);

packages/server/src/server/agent/providers/claude-agent.ts

@@ -625,6 +625,7 @@ class ClaudeAgentSession implements AgentSession {
       this.pendingInterruptPromise = this.interruptActiveTurn().catch((error) => {
         this.logger.warn({ err: error }, "Failed to interrupt during cancel");
       });
+      this.flushPendingToolCalls();
       // Push turn_canceled before ending the queue so consumers get proper lifecycle signals
       queue.push({
         type: "turn_canceled",
@@ -1084,6 +1085,7 @@ class ClaudeAgentSession implements AgentSession {
       // Only emit if not already emitted by requestCancel() (indicated by turnCancelRequested).
       const wasSuperseded = this.currentTurnId !== turnId;
       if (wasSuperseded && !completedNormally && !this.turnCancelRequested) {
+        this.flushPendingToolCalls();
         queue.push({
           type: "turn_canceled",
           provider: "claude",
@@ -1423,6 +1425,21 @@ class ClaudeAgentSession implements AgentSession {
     this.pushEvent({ type: "timeline", item, provider: "claude" });
   }
 
+  private flushPendingToolCalls() {
+    for (const [id, entry] of this.toolUseCache) {
+      if (entry.started) {
+        this.pushToolCall({
+          name: entry.name,
+          status: "failed",
+          callId: id,
+          input: entry.input,
+          error: { message: "Interrupted" },
+        });
+      }
+    }
+    this.toolUseCache.clear();
+  }
+
   private pushToolCall(
     data: Omit<ToolCallTimelineItem, "type">,
     target?: AgentTimelineItem[]