core/agent: drop system todo nag; emit events for synthetic_tool

Remove system strategy (legacy maps to developer). synthetic_tool still
forges the call but uses real stack text as the tool result, and now
yields ToolCall/Result events so the CLI flushes and does not glue nag
text to the next assistant stream.

CLAUDE.md

@@ -86,7 +86,7 @@ Module-level `@tool` handlers. Call `set_workspace_root()` before use.
 - Destructive confirms: `classify_danger` + `ToolRegistry(on_confirm=…)`; CLI default deny; config `confirm_destructive` / `path_denylist`. Soft confirm also for shells/REPLs and `python|bash -c` one-liners (argv + code preview); deny may include a user comment for the model. Session YOLO: `/yolo on|off|once` and `--yes` (skip soft confirms; hard denylists unchanged; `once` expires after the next user turn).
 - **`vcs`**: read-only VCS tools (`vcs_kind` / `vcs_status` / `vcs_diff` / `vcs_log` / `vcs_branch`) via `VcsBackend` protocol; **git** implemented; detectors are pluggable for other systems.
 - **`chat`**: human prompts as tools — `ask_user_line` / `ask_user_choice` / `ask_user_form` (shared `prompting` core).
-- **`todo`**: LIFO stack of **task groups** (not a queue of tasks) — `todo_push` creates one group of siblings; `todo_pop` removes the whole top group; `todo_update` by id; DFS breakdown push[T1,T2]→push[T1.1…]→pop→push[T2.1…]; stored on session row; open items = unfinished work (`[TODO OPEN WORK]`); all-terminal non-empty = hygiene (`[TODO HYGIENE]`); nag channel via `[agent] todo_nag_strategy` (`developer` default | `system` | `user` | `synthetic_tool` | `none`).
+- **`todo`**: LIFO stack of **task groups** (not a queue of tasks) — `todo_push` creates one group of siblings; `todo_pop` removes the whole top group; `todo_update` by id; DFS breakdown push[T1,T2]→push[T1.1…]→pop→push[T2.1…]; stored on session row; open items = unfinished work (`[TODO OPEN WORK]`); all-terminal non-empty = hygiene (`[TODO HYGIENE]`); nag channel via `[agent] todo_nag_strategy` (`developer` default | `user` | `synthetic_tool` | `none`; synthetic emits ToolCall/Result events so CLI flushes; call is forged, result body is real stack text).
 - **`DEFAULT_TOOLS`**: file + process + vcs + chat + todo tool list for a `ToolRegistry`.
 
 ### Prompting (`prompting.py`)

doc/plyngent.example.toml

@@ -19,7 +19,8 @@ path_denylist = ["/secrets/", ".ssh/", ".gnupg/"]
 # Soft context budget in estimated tokens (~4 chars/token when API usage missing).
 max_context_tokens = 200000
 # How open-todo nags are injected into model context:
-# developer (default) | system | user | synthetic_tool | none
+# developer (default) | user | synthetic_tool | none
+# (legacy system is treated as developer)
 # todo_nag_strategy = "developer"
 
 # Optional: custom compact/summarisation prompts (empty = built-in defaults).

src/plyngent/agent/chat.py

@@ -19,7 +19,11 @@ from .budget import (
 )
 from .events import UsageEvent
 from .loop import DEFAULT_MAX_ROUNDS, run_chat_loop
-from .todo_nag import DEFAULT_TODO_NAG_STRATEGY, inject_todo_nag_for_stack, parse_todo_nag_strategy
+from .todo_nag import (
+    DEFAULT_TODO_NAG_STRATEGY,
+    inject_todo_nag_for_stack_with_events,
+    parse_todo_nag_strategy,
+)
 from .usage import TokenUsage
 
 if TYPE_CHECKING:
@@ -300,20 +304,24 @@ class ChatAgent:
         user_index = self._user_index(user_msg)
         if self.todo_stack is not None:
             self.todo_stack.begin_turn()
-            # Non-empty stack at turn start → remind the model before first completion.
-            if not self.todo_stack.is_empty():
-                _ = inject_todo_nag_for_stack(
-                    self.messages,
-                    self.todo_stack,
-                    kind="turn_start",
-                    strategy=self.todo_nag_strategy,
-                )
 
         completed = False
         turn_usage = TokenUsage()
         turn_rounds = 0
         last_request = TokenUsage()
         try:
+            # Turn-start nag before first completion; yield events so CLI flushes
+            # (synthetic_tool → ToolCall/Result chrome, not glued to text).
+            if self.todo_stack is not None and not self.todo_stack.is_empty():
+                _injected, nag_events = inject_todo_nag_for_stack_with_events(
+                    self.messages,
+                    self.todo_stack,
+                    kind="turn_start",
+                    strategy=self.todo_nag_strategy,
+                )
+                for nag_event in nag_events:
+                    yield nag_event
+
             async for event in run_chat_loop(
                 self.client,
                 self.messages,

src/plyngent/agent/loop.py

@@ -37,7 +37,7 @@ from .events import (
     ToolResultEvent,
     UsageEvent,
 )
-from .todo_nag import DEFAULT_TODO_NAG_STRATEGY, inject_todo_nag_for_stack
+from .todo_nag import DEFAULT_TODO_NAG_STRATEGY, inject_todo_nag_for_stack_with_events
 from .usage import resolve_round_usage, token_usage_from_api
 
 if TYPE_CHECKING:
@@ -375,12 +375,14 @@ async def run_chat_loop(  # noqa: C901 — multi-phase tool loop
             if tool_calls is UNSET or not tool_calls or tools is None:
                 if todo_stack is not None and todo_stack.needs_review() and not todo_review_injected:
                     todo_review_injected = True
-                    injected = inject_todo_nag_for_stack(
+                    injected, nag_events = inject_todo_nag_for_stack_with_events(
                         messages,
                         todo_stack,
                         kind="end_of_turn",
                         strategy=todo_nag_strategy,
                     )
+                    for nag_event in nag_events:
+                        yield nag_event
                     if injected:
                         continue
                 return

src/plyngent/agent/todo_nag.py

@@ -12,27 +12,35 @@ from plyngent.lmproto.openai_compatible.model import (
     AssistantFunctionTool,
     AssistantFunctionToolCall,
     DeveloperChatMessage,
-    SystemChatMessage,
     ToolChatMessage,
     UserChatMessage,
 )
 
 if TYPE_CHECKING:
+    from collections.abc import Iterator
+
     from plyngent.lmproto.openai_compatible.model import AnyChatMessage
 
+    from .events import AgentEvent
     from .todo_stack import TodoStack
 
-type TodoNagStrategy = Literal["developer", "system", "user", "synthetic_tool", "none"]
+type TodoNagStrategy = Literal["developer", "user", "synthetic_tool", "none"]
 type TodoNagKind = Literal["turn_start", "end_of_turn"]
 
-TODO_NAG_STRATEGIES: frozenset[str] = frozenset({"developer", "system", "user", "synthetic_tool", "none"})
+TODO_NAG_STRATEGIES: frozenset[str] = frozenset({"developer", "user", "synthetic_tool", "none"})
 DEFAULT_TODO_NAG_STRATEGY: TodoNagStrategy = "developer"
 _SYNTHETIC_TOOL_NAME = "todo_list"
 
 
 def parse_todo_nag_strategy(raw: str | None) -> TodoNagStrategy:
-    """Normalize config/CLI text to a strategy; unknown → developer."""
+    """Normalize config/CLI text to a strategy; unknown → developer.
+
+    Legacy ``system`` is accepted as ``developer`` (mid-turn system was folded
+    into Responses ``instructions`` and was not a useful distinct channel).
+    """
     token = (raw or DEFAULT_TODO_NAG_STRATEGY).strip().lower().replace("-", "_")
+    if token == "system":
+        return "developer"
     if token not in TODO_NAG_STRATEGIES:
         return DEFAULT_TODO_NAG_STRATEGY
     return cast("TodoNagStrategy", token)
@@ -44,7 +52,8 @@ def nag_body(stack: TodoStack, kind: TodoNagKind) -> str:
     return stack.review_prompt()
 
 
-def _append_synthetic_todo_list(messages: list[AnyChatMessage], body: str) -> None:
+def _append_synthetic_todo_list(messages: list[AnyChatMessage], body: str) -> str:
+    """Append forged todo_list call + result. Returns the synthetic tool_call id."""
     call_id = f"todo-nag-{uuid.uuid4().hex[:12]}"
     messages.append(
         AssistantChatMessage(
@@ -61,6 +70,7 @@ def _append_synthetic_todo_list(messages: list[AnyChatMessage], body: str) -> No
         )
     )
     messages.append(ToolChatMessage(tool_call_id=call_id, content=body))
+    return call_id
 
 
 def inject_todo_nag(
@@ -73,26 +83,54 @@ def inject_todo_nag(
 
     Strategies:
     - ``developer`` (default): control-plane message (safe for retry/history).
-    - ``system``: mid-conversation system message.
     - ``user``: looks like a human turn (can confuse retry — use with care).
     - ``synthetic_tool``: forged ``todo_list`` call + result pair (no handler run).
     - ``none``: no injection.
-    """
-    if strategy == "none" or not body.strip():
-        return False
 
-    envelopes: dict[TodoNagStrategy, type] = {
-        "developer": DeveloperChatMessage,
-        "system": SystemChatMessage,
-        "user": UserChatMessage,
-    }
-    if strategy in envelopes:
-        messages.append(envelopes[strategy](content=body))
-        return True
-    if strategy == "synthetic_tool":
-        _append_synthetic_todo_list(messages, body)
-        return True
-    return False
+    Prefer :func:`inject_todo_nag_with_events` when the CLI needs ToolCall/Result
+    events so the display buffer flushes and tool chrome is not glued to text.
+    """
+    return inject_todo_nag_with_events(messages, body, strategy=strategy)[0]
+
+
+def inject_todo_nag_with_events(
+    messages: list[AnyChatMessage],
+    body: str,
+    *,
+    strategy: TodoNagStrategy = DEFAULT_TODO_NAG_STRATEGY,
+) -> tuple[bool, list[AgentEvent]]:
+    """Like :func:`inject_todo_nag`, also return display events for synthetic_tool.
+
+    For ``synthetic_tool``, emits :class:`ToolCallEvent` then
+    :class:`ToolResultEvent` so streaming UIs flush the assistant buffer and
+    show tool chrome (result is real stack text; call was not model-authored).
+    """
+    from .events import ToolCallEvent, ToolResultEvent
+
+    if strategy == "none" or not body.strip():
+        return False, []
+
+    if strategy == "developer":
+        messages.append(DeveloperChatMessage(content=body))
+        return True, []
+    if strategy == "user":
+        messages.append(UserChatMessage(content=body))
+        return True, []
+    # strategy == "synthetic_tool" (only remaining inject path)
+    call_id = _append_synthetic_todo_list(messages, body)
+    assistant = messages[-2]
+    tool_msg = messages[-1]
+    events: list[AgentEvent] = []
+    if isinstance(assistant, AssistantChatMessage):
+        tool_calls = assistant.tool_calls
+        if tool_calls is not UNSET and tool_calls:
+            for call in tool_calls:
+                if getattr(call, "id", None) == call_id:
+                    events.append(ToolCallEvent(tool_call=call))
+                    break
+    if isinstance(tool_msg, ToolChatMessage):
+        events.append(ToolResultEvent(message=tool_msg))
+    return True, events
 
 
 def inject_todo_nag_for_stack(
@@ -104,3 +142,23 @@ def inject_todo_nag_for_stack(
 ) -> bool:
     """Build body from *stack* and inject with *strategy*."""
     return inject_todo_nag(messages, nag_body(stack, kind), strategy=strategy)
+
+
+def inject_todo_nag_for_stack_with_events(
+    messages: list[AnyChatMessage],
+    stack: TodoStack,
+    *,
+    kind: TodoNagKind,
+    strategy: TodoNagStrategy = DEFAULT_TODO_NAG_STRATEGY,
+) -> tuple[bool, list[AgentEvent]]:
+    """Build body from *stack*; inject and return CLI-facing events."""
+    return inject_todo_nag_with_events(
+        messages,
+        nag_body(stack, kind),
+        strategy=strategy,
+    )
+
+
+def iter_synthetic_nag_events(events: list[AgentEvent]) -> Iterator[AgentEvent]:
+    """Yield events for the agent loop (empty if strategy was non-synthetic)."""
+    yield from events

src/plyngent/config/models.py

@@ -28,7 +28,7 @@ class AgentConfig(Struct, omit_defaults=True):
     max_context_tokens: int = 200_000
 
     # How to inject todo stack nags into model context (see agent/todo_nag.py).
-    # developer | system | user | synthetic_tool | none
+    # developer | user | synthetic_tool | none  (legacy "system" → developer)
     todo_nag_strategy: str = "developer"
 
     # Compact / summarisation prompts (empty = use built-in defaults).

tests/test_agent/test_todo_stack.py

@@ -17,7 +17,6 @@ from plyngent.lmproto.openai_compatible.model import (
     ChatCompletionResponse,
     ChatCompletionsParam,
     DeveloperChatMessage,
-    SystemChatMessage,
     ToolChatMessage,
     UserChatMessage,
 )
@@ -127,9 +126,14 @@ def test_parse_todo_nag_strategy() -> None:
     assert parse_todo_nag_strategy("SYNTHETIC-TOOL") == "synthetic_tool"
     assert parse_todo_nag_strategy("nope") == "developer"
     assert parse_todo_nag_strategy(None) == "developer"
+    # Legacy alias — mid-turn system was not a useful Responses channel.
+    assert parse_todo_nag_strategy("system") == "developer"
 
 
 def test_inject_todo_nag_strategies() -> None:
+    from plyngent.agent.events import ToolCallEvent, ToolResultEvent
+    from plyngent.agent.todo_nag import inject_todo_nag_with_events
+
     body = "[TODO OPEN WORK] test"
     messages: list[AnyChatMessage] = []
     assert inject_todo_nag(messages, body, strategy="none") is False
@@ -140,16 +144,13 @@ def test_inject_todo_nag_strategies() -> None:
     assert isinstance(messages[0], DeveloperChatMessage)
     assert body in messages[0].content
 
-    messages = []
-    assert inject_todo_nag(messages, body, strategy="system") is True
-    assert isinstance(messages[0], SystemChatMessage)
-
     messages = []
     assert inject_todo_nag(messages, body, strategy="user") is True
     assert isinstance(messages[0], UserChatMessage)
 
     messages = []
-    assert inject_todo_nag(messages, body, strategy="synthetic_tool") is True
+    ok, events = inject_todo_nag_with_events(messages, body, strategy="synthetic_tool")
+    assert ok is True
     assert len(messages) == 2
     assert isinstance(messages[0], AssistantChatMessage)
     tool_calls = messages[0].tool_calls
@@ -157,6 +158,10 @@ def test_inject_todo_nag_strategies() -> None:
     assert isinstance(messages[1], ToolChatMessage)
     assert body in messages[1].content
     assert messages[1].tool_call_id.startswith("todo-nag-")
+    assert len(events) == 2
+    assert isinstance(events[0], ToolCallEvent)
+    assert isinstance(events[1], ToolResultEvent)
+    assert body in events[1].message.content
 
 
 def test_todo_prompts_signal_undone_work() -> None: