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BlueBubbles v1.9+ webhook payloads for new-message events do not always include a top-level chatGuid field on the message data object. Instead, the chat GUID is nested under data.chats[0].guid. The adapter currently checks five top-level fallback locations (record and payload, snake_case and camelCase, plus payload.guid) but never looks inside the chats array. When none of those top-level fields contain the GUID, the adapter falls through to using the sender's phone/email as the session chat ID. This causes two observable bugs when a user is a participant in both a DM and a group chat with the bot: 1. DM and group sessions merge. Every message from that user ends up with the same session_chat_id (their own address), so the bot cannot distinguish which thread the message came from. 2. Outbound routing becomes ambiguous. _resolve_chat_guid() iterates all chats and returns the first one where the address appears as a participant; group chats typically sort ahead of DMs by activity, so replies and cron messages intended for the DM can land in a group. This was observed in production: a user's morning brief cron delivered to a group chat with his spouse instead of his DM thread. The fix adds a single fallback that extracts chat_guid from record["chats"][0]["guid"] when the top-level fields are empty. The chats array is included in every new-message webhook payload in BB v1.9.9 (verified against a live server). It is backwards compatible: if a future BB version starts including chatGuid at the top level, that still wins. Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>