Harden conversation replies and prioritize newest candidates

docs/services.md

@@ -36,8 +36,9 @@ This is an ownership map, not an API dump. Read the owning implementation and te
 | `services/chat/cache.ts` | Account-scoped cached conversations and sync state | SQLite is durable; do not share caches across accounts. |
 | `services/chat/matrix/username-resolver.ts` | Matrix/Reddit identity mapping | Preserve unresolved internal IDs without leaking them in operator text. |
 | `services/chat/matrix/token-refresher.ts` | Explicit refresh-unavailable behavior | New credentials come from verified extension dumps, not token sniffing. |
-| `services/conversation-automation.ts` | Reply-first policy, claims, retries, handoffs, turn budgets | Snapshot policy; claim before send; reconcile pending claims; fail closed. |
+| `services/conversation-automation.ts` | Reply-first policy, claims, retries, send-time refresh, handoffs, turn budgets | Snapshot policy; claim before send; supersede stale queued work; reconcile pending claims; fail closed. |
 | `services/conversation-state.ts` | Pure conversation parsing/state/safety helpers | Conversation text is untrusted data; keep prompt boundaries explicit. |
+| `services/conversation-boundaries.ts` | Sequence-aware media requests, refusals, and full-stop detection | Short ambiguous replies become boundaries only in the matching request context. |
 | `services/outbound-message-safety.ts` | Final no-proximity/no-meeting rule | This is defense in depth beyond prompts. |
 | `services/conversation-outcome*.ts` | Response outcome classification/recording | Keep analytics attribution account/message scoped. |
 | `services/response-checker.ts` | Inbox/performance response checks and successful examples | Non-overlapping; do not confuse chat sync with outcome maturity. |