diff --git a/assistant/src/calls/call-orchestrator.ts b/assistant/src/calls/call-orchestrator.ts
index 2a795731729..24d466e7f1b 100644
--- a/assistant/src/calls/call-orchestrator.ts
+++ b/assistant/src/calls/call-orchestrator.ts
@@ -51,6 +51,13 @@ export class CallOrchestrator {
     registerCallOrchestrator(callSessionId, this);
   }
 
+  /**
+   * Returns the current orchestrator state.
+   */
+  getState(): OrchestratorState {
+    return this.state;
+  }
+
   /**
    * Handle a final caller utterance from the ConversationRelay.
    */
diff --git a/assistant/src/calls/twilio-routes.ts b/assistant/src/calls/twilio-routes.ts
index 998ae124e6f..aacbfeb36e7 100644
--- a/assistant/src/calls/twilio-routes.ts
+++ b/assistant/src/calls/twilio-routes.ts
@@ -218,7 +218,15 @@ export async function handleCallAnswer(req: Request, callSessionId: string): Pro
     return Response.json({ error: 'No active orchestrator for this call' }, { status: 409 });
   }
 
-  // Mark question as answered
+  if (orchestrator.getState() !== 'waiting_on_user') {
+    log.warn(
+      { callSessionId, state: orchestrator.getState() },
+      'handleCallAnswer: orchestrator is not in waiting_on_user state',
+    );
+    return Response.json({ error: 'Orchestrator is not waiting for an answer' }, { status: 409 });
+  }
+
+  // Mark question as answered — only after confirming the orchestrator is ready
   answerPendingQuestion(question.id, body.answer);
 
   // Route answer to the orchestrator
diff --git a/assistant/src/tools/calls/call-end.ts b/assistant/src/tools/calls/call-end.ts
index e040725394b..091ca8e5e2e 100644
--- a/assistant/src/tools/calls/call-end.ts
+++ b/assistant/src/tools/calls/call-end.ts
@@ -5,6 +5,7 @@ import { registerTool } from '../registry.js';
 import { getCallSession, updateCallSession } from '../../calls/call-store.js';
 import { getCallOrchestrator, unregisterCallOrchestrator } from '../../calls/call-state.js';
 import { activeRelayConnections } from '../../calls/relay-server.js';
+import { TwilioConversationRelayProvider } from '../../calls/twilio-provider.js';
 import { getLogger } from '../../util/logger.js';
 
 const log = getLogger('call-end');
@@ -61,6 +62,17 @@ class CallEndTool implements Tool {
 
       log.info({ callSessionId, reason }, 'Ending call');
 
+      // Terminate the call via the provider API so Twilio hangs up,
+      // even if the relay WebSocket is not connected.
+      if (session.providerCallSid) {
+        try {
+          const provider = new TwilioConversationRelayProvider();
+          await provider.endCall(session.providerCallSid);
+        } catch (endErr) {
+          log.warn({ err: endErr, callSessionId, callSid: session.providerCallSid }, 'Failed to terminate call via provider API — proceeding with cleanup');
+        }
+      }
+
       // End the relay connection if active
       const relayConnection = activeRelayConnections.get(callSessionId);
       if (relayConnection) {
diff --git a/assistant/src/tools/calls/call-start.ts b/assistant/src/tools/calls/call-start.ts
index c69030f134b..f031bd48d25 100644
--- a/assistant/src/tools/calls/call-start.ts
+++ b/assistant/src/tools/calls/call-start.ts
@@ -70,6 +70,10 @@ class CallStartTool implements Tool {
 
     const callContext = input.context as string | undefined;
 
+    // Create session outside the try block so it's available in the catch block
+    // for marking as failed if the provider call fails.
+    let sessionId: string | null = null;
+
     try {
       const config = getTwilioConfig();
       const provider = new TwilioConversationRelayProvider();
@@ -81,6 +85,7 @@ class CallStartTool implements Tool {
         toNumber: phoneNumber,
         task: callContext ? `${task}\n\nContext: ${callContext}` : task,
       });
+      sessionId = session.id;
 
       log.info({ callSessionId: session.id, to: phoneNumber, task }, 'Initiating outbound call');
 
@@ -111,6 +116,16 @@ class CallStartTool implements Tool {
     } catch (err) {
       const msg = err instanceof Error ? err.message : String(err);
       log.error({ err, phoneNumber }, 'Failed to initiate call');
+
+      // Mark the session as failed so it doesn't stay in 'initiated' state
+      if (sessionId) {
+        updateCallSession(sessionId, {
+          status: 'failed',
+          endedAt: Date.now(),
+          lastError: msg,
+        });
+      }
+
       return { content: `Error initiating call: ${msg}`, isError: true };
     }
   }