diff --git a/assistant/src/calls/call-orchestrator.ts b/assistant/src/calls/call-orchestrator.ts
index d8e459c6daf..953842ba84d 100644
--- a/assistant/src/calls/call-orchestrator.ts
+++ b/assistant/src/calls/call-orchestrator.ts
@@ -22,6 +22,7 @@ import type { RelayConnection } from './relay-server.js';
 import { registerCallOrchestrator, unregisterCallOrchestrator, fireCallQuestionNotifier, fireCallCompletionNotifier, fireCallTranscriptNotifier } from './call-state.js';
 import type { PromptSpeakerContext } from './speaker-identification.js';
 import { addPointerMessage, formatDuration } from './call-pointer-messages.js';
+import * as conversationStore from '../memory/conversation-store.js';
 import { dispatchGuardianQuestion } from './guardian-dispatch.js';
 import type { ServerMessage } from '../daemon/ipc-contract.js';
 
@@ -452,6 +453,13 @@ export class CallOrchestrator {
       if (spokenText.length > 0) {
         const session = getCallSession(this.callSessionId);
         if (session) {
+          // Persist assistant transcript to the voice conversation so it
+          // survives even when no live daemon Session is listening.
+          conversationStore.addMessage(
+            session.conversationId,
+            'assistant',
+            JSON.stringify([{ type: 'text', text: spokenText }]),
+          );
           fireCallTranscriptNotifier(session.conversationId, this.callSessionId, 'assistant', spokenText);
         }
       }
diff --git a/assistant/src/calls/relay-server.ts b/assistant/src/calls/relay-server.ts
index 7708c3991ff..3cd8046daa3 100644
--- a/assistant/src/calls/relay-server.ts
+++ b/assistant/src/calls/relay-server.ts
@@ -454,6 +454,13 @@ export class RelayConnection {
 
     const session = getCallSession(this.callSessionId);
     if (session) {
+      // Persist caller transcript to the voice conversation so it survives
+      // even when no live daemon Session is listening.
+      conversationStore.addMessage(
+        session.conversationId,
+        'user',
+        JSON.stringify([{ type: 'text', text: msg.voicePrompt }]),
+      );
       fireCallTranscriptNotifier(session.conversationId, this.callSessionId, 'caller', msg.voicePrompt);
     }
 
diff --git a/assistant/src/config/bundled-skills/phone-calls/SKILL.md b/assistant/src/config/bundled-skills/phone-calls/SKILL.md
index a1193fbb153..a85206e2414 100644
--- a/assistant/src/config/bundled-skills/phone-calls/SKILL.md
+++ b/assistant/src/config/bundled-skills/phone-calls/SKILL.md
@@ -198,7 +198,7 @@ An optional verification step where the callee must enter a numeric code via the
 | Setting | Description | Default |
 |---|---|---|
 | `calls.verification.enabled` | Enable DTMF callee verification | `false` |
-| `calls.verification.codeLength` | Number of digits in the verification code | `4` |
+| `calls.verification.codeLength` | Number of digits in the verification code | `6` |
 
 ## Optional: Higher Quality Voice with ElevenLabs
 
diff --git a/assistant/src/daemon/session-process.ts b/assistant/src/daemon/session-process.ts
index 1afea07a075..4878fece246 100644
--- a/assistant/src/daemon/session-process.ts
+++ b/assistant/src/daemon/session-process.ts
@@ -236,7 +236,6 @@ export async function processMessage(
   if (guardianDelivery) {
     const guardianRequest = getGuardianActionRequest(guardianDelivery.requestId);
     if (guardianRequest && guardianRequest.status === 'pending') {
-      const resolved = resolveGuardianActionRequest(guardianRequest.id, content, 'mac');
       const userMsg = createUserMessage(content, attachments);
       const persisted = conversationStore.addMessage(
         session.conversationId,
@@ -245,25 +244,36 @@ export async function processMessage(
       );
       session.messages.push(userMsg);
 
-      if (resolved) {
-        void answerCall({ callSessionId: guardianRequest.callSessionId, answer: content });
-        const confirmMsg = createAssistantMessage('Your answer has been relayed to the call.');
+      // Attempt to deliver the answer to the call first. Only resolve
+      // the guardian action request if answerCall succeeds, so that a
+      // failed delivery leaves the request pending for retry from
+      // another channel.
+      const answerResult = await answerCall({ callSessionId: guardianRequest.callSessionId, answer: content });
+
+      if ('ok' in answerResult && answerResult.ok) {
+        const resolved = resolveGuardianActionRequest(guardianRequest.id, content, 'mac');
+        const replyText = resolved
+          ? 'Your answer has been relayed to the call.'
+          : 'This question has already been answered from another channel.';
+        const replyMsg = createAssistantMessage(replyText);
         conversationStore.addMessage(
           session.conversationId,
           'assistant',
-          JSON.stringify(confirmMsg.content),
+          JSON.stringify(replyMsg.content),
         );
-        session.messages.push(confirmMsg);
-        onEvent({ type: 'assistant_text_delta', text: 'Your answer has been relayed to the call.' });
+        session.messages.push(replyMsg);
+        onEvent({ type: 'assistant_text_delta', text: replyText });
       } else {
-        const staleMsg = createAssistantMessage('This question has already been answered from another channel.');
+        const errorDetail = 'error' in answerResult ? answerResult.error : 'Unknown error';
+        log.warn({ callSessionId: guardianRequest.callSessionId, error: errorDetail }, 'answerCall failed for mac guardian answer');
+        const failMsg = createAssistantMessage('Failed to deliver your answer to the call. Please try again.');
         conversationStore.addMessage(
           session.conversationId,
           'assistant',
-          JSON.stringify(staleMsg.content),
+          JSON.stringify(failMsg.content),
         );
-        session.messages.push(staleMsg);
-        onEvent({ type: 'assistant_text_delta', text: 'This question has already been answered from another channel.' });
+        session.messages.push(failMsg);
+        onEvent({ type: 'assistant_text_delta', text: 'Failed to deliver your answer to the call. Please try again.' });
       }
       onEvent({ type: 'message_complete', sessionId: session.conversationId });
       return persisted.id;