Fix false autonomous safety handoffs

src/services/conversation-automation.ts

@@ -12,10 +12,10 @@ import {
   chooseConversationIntent,
   conversationMessageFingerprint,
   createConversationAutomationState,
-  isSafeHybridMediaAsk,
-  isSafeR4RReply,
+  hybridMediaAskSafetyFailure,
   LEGACY_AUTOMATED_CONVERSATION_TURNS,
   mergeConversationState,
+  r4rReplySafetyFailure,
   remainingAutomationTurns,
   type ConversationState,
 } from './conversation-state.js';
@@ -355,22 +355,32 @@ export class ConversationAutomationService {
     if (isLegacy && intent.kind !== 'media-ask') {
       return this.finish(conversation, conversationId, state, incomingKey, 'human-required', intent.reason);
     }
-    const reply = isLegacy
-      ? await this.ai.generateMediaAsk(mapped, conversation.username, state, intent)
+    const generatePlannedReply = () => isLegacy
+      ? this.ai.generateMediaAsk(mapped, conversation.username, state, intent)
       : isHybridMediaAsk
-        ? await this.ai.generateR4RMediaAsk(mapped, conversation.username, state)
-        : await this.ai.generateReply(mapped, conversation.username, state, intent);
-    const safeReply = isLegacy || isHybridMediaAsk
-      ? isSafeHybridMediaAsk(reply)
-      : isSafeR4RReply(reply);
-    if (!safeReply) {
+        ? this.ai.generateR4RMediaAsk(mapped, conversation.username, state)
+        : this.ai.generateReply(mapped, conversation.username, state, intent);
+    let reply = await generatePlannedReply();
+    let safetyFailure = isLegacy || isHybridMediaAsk
+      ? hybridMediaAskSafetyFailure(reply)
+      : r4rReplySafetyFailure(reply);
+    if ((isLegacy || isHybridMediaAsk)
+      && safetyFailure === 'media ask does not contain a recognizable image or video request') {
+      this.logger.warn?.(
+        `[automation] Regenerating media ask for u/${conversation.username}; the first response did not contain a recognizable request`,
+      );
+      reply = await generatePlannedReply();
+      safetyFailure = hybridMediaAskSafetyFailure(reply);
+    }
+    if (safetyFailure) {
+      const outputKind = isLegacy || isHybridMediaAsk ? 'media ask' : 'reply';
       return this.finish(
         conversation,
         conversationId,
         state,
         incomingKey,
         'human-required',
-        'The generated reply failed autonomous safety checks.',
+        `The generated ${outputKind} was rejected: ${safetyFailure}.`,
       );
     }
     if (this.dryRun) {