fix(gateway/bluebubbles): align iMessage delivery with non-editable UX

gateway/platforms/bluebubbles.py

@@ -99,6 +99,7 @@ def _normalize_server_url(raw: str) -> str:
 
 class BlueBubblesAdapter(BasePlatformAdapter):
     platform = Platform.BLUEBUBBLES
+    SUPPORTS_MESSAGE_EDITING = False
     MAX_MESSAGE_LENGTH = MAX_TEXT_LENGTH
 
     def __init__(self, config: PlatformConfig):
@@ -391,6 +392,13 @@ class BlueBubblesAdapter(BasePlatformAdapter):
     # Text sending
     # ------------------------------------------------------------------
 
+    @staticmethod
+    def truncate_message(content: str, max_length: int = MAX_TEXT_LENGTH) -> List[str]:
+        # Use the base splitter but skip pagination indicators — iMessage
+        # bubbles flow naturally without "(1/3)" suffixes.
+        chunks = BasePlatformAdapter.truncate_message(content, max_length)
+        return [re.sub(r"\s*\(\d+/\d+\)$", "", c) for c in chunks]
+
     async def send(
         self,
         chat_id: str,
@@ -398,10 +406,19 @@ class BlueBubblesAdapter(BasePlatformAdapter):
         reply_to: Optional[str] = None,
         metadata: Optional[Dict[str, Any]] = None,
     ) -> SendResult:
-        text = strip_markdown(content or "")
+        text = self.format_message(content)
         if not text:
             return SendResult(success=False, error="BlueBubbles send requires text")
-        chunks = self.truncate_message(text, max_length=self.MAX_MESSAGE_LENGTH)
+        # Split on paragraph breaks first (double newlines) so each thought
+        # becomes its own iMessage bubble, then truncate any that are still
+        # too long.
+        paragraphs = [p.strip() for p in re.split(r'\n\s*\n', text) if p.strip()]
+        chunks: List[str] = []
+        for para in (paragraphs or [text]):
+            if len(para) <= self.MAX_MESSAGE_LENGTH:
+                chunks.append(para)
+            else:
+                chunks.extend(self.truncate_message(para, max_length=self.MAX_MESSAGE_LENGTH))
         last = SendResult(success=True)
         for chunk in chunks:
             guid = await self._resolve_chat_guid(chat_id)

gateway/session.py

@@ -285,6 +285,18 @@ def build_session_context_prompt(
             "Do not promise to perform these actions. If the user asks, explain "
             "that you can only read messages sent directly to you and respond."
         )
+    elif context.source.platform == Platform.BLUEBUBBLES:
+        lines.append("")
+        lines.append(
+            "**Platform notes:** You are responding via iMessage. "
+            "Keep responses short and conversational — think texts, not essays. "
+            "Structure longer replies as separate short thoughts, each separated "
+            "by a blank line (double newline). Each block between blank lines "
+            "will be delivered as its own iMessage bubble, so write accordingly: "
+            "one idea per bubble, 1–3 sentences each. "
+            "If the user needs a detailed answer, give the short version first "
+            "and offer to elaborate."
+        )
 
     # Connected platforms
     platforms_list = ["local (files on this machine)"]

tests/gateway/test_bluebubbles.py

@@ -66,6 +66,37 @@ class TestBlueBubblesHelpers:
 
         assert check_bluebubbles_requirements() is True
 
+    def test_supports_message_editing_is_false(self, monkeypatch):
+        adapter = _make_adapter(monkeypatch)
+        assert adapter.SUPPORTS_MESSAGE_EDITING is False
+
+    def test_truncate_message_omits_pagination_suffixes(self, monkeypatch):
+        adapter = _make_adapter(monkeypatch)
+        chunks = adapter.truncate_message("abcdefghij", max_length=6)
+        assert len(chunks) > 1
+        assert "".join(chunks) == "abcdefghij"
+        assert all("(" not in chunk for chunk in chunks)
+
+    @pytest.mark.asyncio
+    async def test_send_splits_paragraphs_into_multiple_bubbles(self, monkeypatch):
+        adapter = _make_adapter(monkeypatch)
+        sent = []
+
+        async def fake_resolve_chat_guid(chat_id):
+            return "iMessage;-;user@example.com"
+
+        async def fake_api_post(path, payload):
+            sent.append(payload["message"])
+            return {"data": {"guid": f"msg-{len(sent)}"}}
+
+        monkeypatch.setattr(adapter, "_resolve_chat_guid", fake_resolve_chat_guid)
+        monkeypatch.setattr(adapter, "_api_post", fake_api_post)
+
+        result = await adapter.send("user@example.com", "first thought\n\nsecond thought")
+
+        assert result.success is True
+        assert sent == ["first thought", "second thought"]
+
     def test_format_message_strips_markdown(self, monkeypatch):
         adapter = _make_adapter(monkeypatch)
         assert adapter.format_message("**Hello** `world`") == "Hello world"

tests/gateway/test_run_progress_topics.py

@@ -58,6 +58,13 @@ class ProgressCaptureAdapter(BasePlatformAdapter):
         return {"id": chat_id}
 
 
+class NonEditingProgressCaptureAdapter(ProgressCaptureAdapter):
+    SUPPORTS_MESSAGE_EDITING = False
+
+    async def edit_message(self, chat_id, message_id, content) -> SendResult:
+        raise AssertionError("non-editable adapters should not receive edit_message calls")
+
+
 class FakeAgent:
     def __init__(self, **kwargs):
         self.tool_progress_callback = kwargs.get("tool_progress_callback")
@@ -502,6 +509,7 @@ async def _run_with_agent(
     chat_id="-1001",
     chat_type="group",
     thread_id="17585",
+    adapter_cls=ProgressCaptureAdapter,
 ):
     if config_data:
         import yaml
@@ -516,7 +524,7 @@ async def _run_with_agent(
     fake_run_agent.AIAgent = agent_cls
     monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
 
-    adapter = ProgressCaptureAdapter(platform=platform)
+    adapter = adapter_cls(platform=platform)
     runner = _make_runner(adapter)
     gateway_run = importlib.import_module("gateway.run")
     if config_data and "streaming" in config_data:
@@ -666,6 +674,26 @@ async def test_run_agent_interim_commentary_works_with_tool_progress_off(monkeyp
     assert any(call["content"] == "I'll inspect the repo first." for call in adapter.sent)
 
 
+@pytest.mark.asyncio
+async def test_run_agent_bluebubbles_uses_commentary_send_path_for_quick_replies(monkeypatch, tmp_path):
+    adapter, result = await _run_with_agent(
+        monkeypatch,
+        tmp_path,
+        CommentaryAgent,
+        session_id="sess-bluebubbles-commentary",
+        config_data={"display": {"interim_assistant_messages": True}},
+        platform=Platform.BLUEBUBBLES,
+        chat_id="iMessage;-;user@example.com",
+        chat_type="dm",
+        thread_id=None,
+        adapter_cls=NonEditingProgressCaptureAdapter,
+    )
+
+    assert result.get("already_sent") is not True
+    assert [call["content"] for call in adapter.sent] == ["I'll inspect the repo first."]
+    assert adapter.edits == []
+
+
 @pytest.mark.asyncio
 async def test_run_agent_previewed_final_marks_already_sent(monkeypatch, tmp_path):
     adapter, result = await _run_with_agent(

tests/gateway/test_session.py

@@ -185,6 +185,25 @@ class TestBuildSessionContextPrompt:
         assert "Telegram" in prompt
         assert "Home Chat" in prompt
 
+    def test_bluebubbles_prompt_mentions_short_conversational_i_message_format(self):
+        config = GatewayConfig(
+            platforms={
+                Platform.BLUEBUBBLES: PlatformConfig(enabled=True, extra={"server_url": "http://localhost:1234", "password": "secret"}),
+            },
+        )
+        source = SessionSource(
+            platform=Platform.BLUEBUBBLES,
+            chat_id="iMessage;-;user@example.com",
+            chat_name="Ben",
+            chat_type="dm",
+        )
+        ctx = build_session_context(source, config)
+        prompt = build_session_context_prompt(ctx)
+
+        assert "responding via iMessage" in prompt
+        assert "short and conversational" in prompt
+        assert "blank line" in prompt
+
     def test_discord_prompt(self):
         config = GatewayConfig(
             platforms={