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) {

src/services/conversation-boundaries.ts

@@ -4,7 +4,7 @@ export interface BoundaryMessage {
 }
 
 const MEDIA_NOUN = String.raw`(?:pic|pics|picture|pictures|photo|photos|selfie|selfies|snap|snaps|image|images|video|videos|nude|nudes|content)`;
-const MEDIA_VERB = String.raw`(?:send(?:ing)?|shar(?:e|ing)|show(?:ing)?|giv(?:e|ing)|drop(?:ping)?|swap(?:ping)?|trad(?:e|ing))`;
+const MEDIA_VERB = String.raw`(?:send(?:ing)?|shar(?:e|ing)|show(?:ing)?|giv(?:e|ing)|drop(?:ping)?|swap(?:ping)?|trad(?:e|ing)|snap(?:ping)?|tak(?:e|ing)|attach(?:ed|ing)?|upload(?:ed|ing)?)`;
 
 const EXPLICIT_MEDIA_REFUSAL_PATTERNS = [
   new RegExp(String.raw`\b(?:no|not|never|won't|wouldn't|don't|do not|can't|cannot)\b[^.\n]{0,60}\b${MEDIA_NOUN}\b`, 'i'),

src/services/conversation-state.ts

@@ -88,7 +88,6 @@ export function conversationMessageFingerprint(message: string): string {
 }
 
 export function remainingAutomationTurns(state: ConversationState): number {
-  if (state.automation.status !== 'active') return 0;
   return Math.max(0, state.automation.maxAutomatedTurns - state.automation.turnsUsed);
 }
 
@@ -191,28 +190,65 @@ export function formatConversationAsUntrustedData(messages: ConversationMessage[
   return `BEGIN UNTRUSTED CONVERSATION DATA\n${rows.join('\n')}\nEND UNTRUSTED CONVERSATION DATA`;
 }
 
+export type ConversationReplySafetyFailure =
+  | 'empty reply'
+  | 'reply exceeds 600 characters'
+  | 'reply contains instruction or prompt leakage'
+  | 'reply implies shared location or an in-person meeting'
+  | 'reply exceeds the three-sentence limit'
+  | 'reply solicits media outside the configured media-ask phase'
+  | 'media ask does not contain a recognizable image or video request'
+  | 'media ask requests explicit or sexual content'
+  | 'media ask uses coercive or pressuring language';
+
+/** Explain why generated text violates the shared autonomous reply contract. */
+export function conversationReplySafetyFailure(message: string): ConversationReplySafetyFailure | null {
+  const trimmed = message.trim();
+  if (!trimmed) return 'empty reply';
+  if (trimmed.length > 600) return 'reply exceeds 600 characters';
+  if (/\b(as an ai|system prompt|begin untrusted|end untrusted|ignore (all|previous) instructions)\b/i.test(trimmed)) {
+    return 'reply contains instruction or prompt leakage';
+  }
+  if (!isSafeOutboundMessage(trimmed)) return 'reply implies shared location or an in-person meeting';
+  const sentences = trimmed.match(/[^.!?]+[.!?]+/g) ?? [];
+  if (sentences.length > 3) return 'reply exceeds the three-sentence limit';
+  return null;
+}
+
 /** Reject obvious instruction leakage and outputs that disregard the reply length contract. */
 export function isSafeConversationReply(message: string): boolean {
-  const trimmed = message.trim();
-  if (!trimmed || trimmed.length > 600) return false;
-  if (/\b(as an ai|system prompt|begin untrusted|end untrusted|ignore (all|previous) instructions)\b/i.test(trimmed)) return false;
-  if (!isSafeOutboundMessage(trimmed)) return false;
-  const sentences = trimmed.match(/[^.!?]+[.!?]+/g) ?? [];
-  return sentences.length <= 3;
+  return conversationReplySafetyFailure(message) === null;
+}
+
+export function r4rReplySafetyFailure(message: string): ConversationReplySafetyFailure | null {
+  const sharedFailure = conversationReplySafetyFailure(message);
+  if (sharedFailure) return sharedFailure;
+  return containsMediaRequest(message)
+    ? 'reply solicits media outside the configured media-ask phase'
+    : null;
 }
 
 /** R4R automation may converse and flirt, but it must never solicit sexual media. */
 export function isSafeR4RReply(message: string): boolean {
-  if (!isSafeConversationReply(message)) return false;
-  return !containsMediaRequest(message);
+  return r4rReplySafetyFailure(message) === null;
+}
+
+export function hybridMediaAskSafetyFailure(message: string): ConversationReplySafetyFailure | null {
+  const sharedFailure = conversationReplySafetyFailure(message);
+  if (sharedFailure) return sharedFailure;
+  if (!containsMediaRequest(message)) return 'media ask does not contain a recognizable image or video request';
+  if (/\b(nude|nudes|naked|explicit|nsfw|sexy pic|sexual)\b/i.test(message)) {
+    return 'media ask requests explicit or sexual content';
+  }
+  if (/\b(must|prove|dare|owe|have to|need to)\b/i.test(message)) {
+    return 'media ask uses coercive or pressuring language';
+  }
+  return null;
 }
 
 /** The hybrid policy gets one optional, non-explicit image request after rapport. */
 export function isSafeHybridMediaAsk(message: string): boolean {
-  if (!isSafeConversationReply(message)) return false;
-  if (!containsMediaRequest(message)) return false;
-  if (/\b(nude|nudes|naked|explicit|nsfw|sexy pic|sexual)\b/i.test(message)) return false;
-  return !/\b(must|prove|dare|owe|have to|need to)\b/i.test(message);
+  return hybridMediaAskSafetyFailure(message) === null;
 }
 
 export function serializeConversationState(state: ConversationState): string {