Fix false autonomous safety handoffs

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 {