diff --git a/gateway/platforms/bluebubbles.py b/gateway/platforms/bluebubbles.py
index fc179154f..909a0be66 100644
--- a/gateway/platforms/bluebubbles.py
+++ b/gateway/platforms/bluebubbles.py
@@ -835,6 +835,12 @@ class BlueBubblesAdapter(BasePlatformAdapter):
             payload.get("chat_guid"),
             payload.get("guid"),
         )
+        # Fallback: BlueBubbles v1.9+ webhook payloads omit top-level chatGuid;
+        # the chat GUID is nested under data.chats[0].guid instead.
+        if not chat_guid:
+            _chats = record.get("chats") or []
+            if _chats and isinstance(_chats[0], dict):
+                chat_guid = _chats[0].get("guid") or _chats[0].get("chatGuid")
         chat_identifier = self._value(
             record.get("chatIdentifier"),
             record.get("identifier"),
diff --git a/tests/gateway/test_bluebubbles.py b/tests/gateway/test_bluebubbles.py
index 86220d440..639f81ae0 100644
--- a/tests/gateway/test_bluebubbles.py
+++ b/tests/gateway/test_bluebubbles.py
@@ -167,6 +167,63 @@ class TestBlueBubblesWebhookParsing:
             chat_identifier = sender
         assert chat_identifier == "user@example.com"
 
+    def test_webhook_extracts_chat_guid_from_chats_array_dm(self, monkeypatch):
+        """BB v1.9+ webhook payloads omit top-level chatGuid; GUID is in chats[0].guid."""
+        adapter = _make_adapter(monkeypatch)
+        payload = {
+            "type": "new-message",
+            "data": {
+                "guid": "MESSAGE-GUID",
+                "text": "hello",
+                "handle": {"address": "+15551234567"},
+                "isFromMe": False,
+                "chats": [
+                    {"guid": "any;-;+15551234567", "chatIdentifier": "+15551234567"}
+                ],
+            },
+        }
+        record = adapter._extract_payload_record(payload) or {}
+        chat_guid = adapter._value(
+            record.get("chatGuid"),
+            payload.get("chatGuid"),
+            record.get("chat_guid"),
+            payload.get("chat_guid"),
+            payload.get("guid"),
+        )
+        if not chat_guid:
+            _chats = record.get("chats") or []
+            if _chats and isinstance(_chats[0], dict):
+                chat_guid = _chats[0].get("guid") or _chats[0].get("chatGuid")
+        assert chat_guid == "any;-;+15551234567"
+
+    def test_webhook_extracts_chat_guid_from_chats_array_group(self, monkeypatch):
+        """Group chat GUIDs contain ;+; and must be extracted from chats array."""
+        adapter = _make_adapter(monkeypatch)
+        payload = {
+            "type": "new-message",
+            "data": {
+                "guid": "MESSAGE-GUID",
+                "text": "hello everyone",
+                "handle": {"address": "+15551234567"},
+                "isFromMe": False,
+                "isGroup": True,
+                "chats": [{"guid": "any;+;chat-uuid-abc123"}],
+            },
+        }
+        record = adapter._extract_payload_record(payload) or {}
+        chat_guid = adapter._value(
+            record.get("chatGuid"),
+            payload.get("chatGuid"),
+            record.get("chat_guid"),
+            payload.get("chat_guid"),
+            payload.get("guid"),
+        )
+        if not chat_guid:
+            _chats = record.get("chats") or []
+            if _chats and isinstance(_chats[0], dict):
+                chat_guid = _chats[0].get("guid") or _chats[0].get("chatGuid")
+        assert chat_guid == "any;+;chat-uuid-abc123"
+
     def test_extract_payload_record_accepts_list_data(self, monkeypatch):
         adapter = _make_adapter(monkeypatch)
         payload = {