cli/repl: keep second Ctrl+C inside the REPL

src/plyngent/cli/repl.py

@@ -22,6 +22,12 @@ def _echo_user(text: str) -> None:
         click.echo(text)
 
 
+def _echo_interrupted() -> None:
+    click.echo()
+    click.secho("interrupted", fg="yellow")
+    click.echo()
+
+
 async def run_repl(state: ReplState) -> None:
     """Interactive chat loop with readline editing, history, and Tab completion."""
     setup_readline(state)
@@ -47,7 +53,11 @@ async def run_repl(state: ReplState) -> None:
             continue
 
         if entry.startswith("/"):
-            cont = await handle_slash(state, entry)
+            try:
+                cont = await handle_slash(state, entry)
+            except KeyboardInterrupt:
+                _echo_interrupted()
+                continue
             if not cont:
                 break
             if state.pending_user_text is not None:
@@ -56,6 +66,8 @@ async def run_repl(state: ReplState) -> None:
                 _echo_user(text)
                 try:
                     _ = await run_user_text_with_retries(state.agent, text)
+                except KeyboardInterrupt:
+                    _echo_interrupted()
                 finally:
                     state.expire_yolo_once()
             continue
@@ -63,5 +75,7 @@ async def run_repl(state: ReplState) -> None:
         _echo_user(entry)
         try:
             _ = await run_user_text_with_retries(state.agent, entry)
+        except KeyboardInterrupt:
+            _echo_interrupted()
         finally:
             state.expire_yolo_once()

src/plyngent/cli/retry.py

@@ -131,20 +131,36 @@ def _echo_turn_usage(agent: ChatAgent) -> None:
     click.secho(f"[{'; '.join(parts)}]", fg="bright_black")
 
 
-async def _wait_for_retry(attempt: int, max_retries: int, wait: float) -> bool:
-    click.secho(
-        f"auto-retry {attempt}/{max_retries} in {wait:g}s (Ctrl+C to cancel; then /retry later)",
-        fg="yellow",
-    )
+def _echo_cancel_lines(*lines: str) -> None:
+    """Print post-cancel lines, treating a further Ctrl+C as benign.
+
+    After a turn-cancel the asyncio SIGINT handler is removed, so a second
+    Ctrl+C during this output would otherwise raise KeyboardInterrupt and
+    exit the REPL instead of returning to the prompt.
+    """
     try:
+        for line in lines:
+            if line:
+                click.secho(line, fg="yellow")
+            else:
+                click.echo()
+    except KeyboardInterrupt:
+        pass
+
+
+async def _wait_for_retry(attempt: int, max_retries: int, wait: float) -> bool:
+    try:
+        click.secho(
+            f"auto-retry {attempt}/{max_retries} in {wait:g}s (Ctrl+C to cancel; then /retry later)",
+            fg="yellow",
+        )
         ok = await sleep_cancellable(wait)
     except KeyboardInterrupt:
         ok = False
     if not ok:
-        click.secho("auto-retry cancelled; use /retry to try again", fg="yellow")
-        click.echo()
+        _echo_cancel_lines("auto-retry cancelled; use /retry to try again", "")
         return False
-    click.secho(f"retrying ({attempt}/{max_retries})…", fg="yellow")
+    _echo_cancel_lines(f"retrying ({attempt}/{max_retries})…")
     return True
 
 
@@ -170,17 +186,10 @@ async def run_turn_with_retries(
             await run_cancellable(render_events(current()))
         except asyncio.CancelledError:
             # Do not auto-retry cancelled turns — user intent was stop, not retry.
-            click.echo()
-            click.secho(
-                "cancelled; user message kept — use /retry to try again",
-                fg="yellow",
-            )
-            click.echo()
+            _echo_cancel_lines("", "cancelled; user message kept — use /retry to try again", "")
             return False
         except KeyboardInterrupt:
-            click.echo()
-            click.secho("interrupted", fg="yellow")
-            click.echo()
+            _echo_cancel_lines("", "interrupted", "")
             return False
         except Exception as exc:  # noqa: BLE001 — surface and optionally retry
             click.secho(f"error: {exc}", fg="red")

tests/test_cli/test_repl_commands.py

@@ -566,3 +566,30 @@ async def test_status_shows_context_tokens(state: ReplState, capsys: pytest.Capt
     out2 = capsys.readouterr().out
     assert "context_tokens=1234/" in out2
     assert "(api)" in out2
+
+
+async def test_repl_ctrl_c_from_turn_returns_to_prompt(
+    state: ReplState,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """A Ctrl+C escaping a turn lands back at the prompt, not out of the REPL."""
+    from plyngent.cli import repl as repl_mod
+    from plyngent.cli.repl import run_repl
+
+    calls: dict[str, int] = {"reads": 0}
+
+    def fake_read_entry() -> str:
+        calls["reads"] += 1
+        if calls["reads"] >= 2:
+            raise EOFError
+        return "hello"
+
+    async def interrupted_turn(_agent: object, _text: str) -> bool:
+        raise KeyboardInterrupt
+
+    monkeypatch.setattr(repl_mod, "setup_readline", lambda _state: None)
+    monkeypatch.setattr(repl_mod, "read_repl_entry", fake_read_entry)
+    monkeypatch.setattr(repl_mod, "run_user_text_with_retries", interrupted_turn)
+
+    await run_repl(state)  # must return normally (EOF), never raise KeyboardInterrupt
+    assert calls["reads"] == 2

tests/test_cli/test_retry.py

@@ -8,6 +8,7 @@ from plyngent.agent import ChatAgent
 from plyngent.cli.retry import (
     DEFAULT_MAX_AUTO_RETRIES,
     DEFAULT_RETRY_DELAYS_SECONDS,
+    _wait_for_retry,
     default_retry_delays,
     retry_pending_with_retries,
     run_turn_with_retries,
@@ -199,6 +200,102 @@ async def test_cancel_turn_rolls_back_and_sets_pending() -> None:
     await store.close()
 
 
+async def test_second_ctrl_c_during_cancel_message_stays_in_repl(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Regression: a second Ctrl+C during the cancel message must not exit.
+
+    After the turn task is cancelled the asyncio SIGINT handler is gone, so the
+    second Ctrl+C arrives as a KeyboardInterrupt while the "cancelled" message
+    is printing. It must be swallowed and control must return to the REPL
+    (``False``), not propagate out of ``run_turn_with_retries``.
+    """
+    import asyncio
+
+    calls: list[int] = [0]
+
+    def raiser(message: object = None, **kwargs: object) -> None:
+        calls[0] += 1
+        if calls[0] == 1:
+            raise KeyboardInterrupt
+
+    monkeypatch.setattr("plyngent.cli.retry.click.secho", raiser)
+
+    store = await MemoryStore.open(DatabaseConfig())
+    session = await store.create_session(name="t")
+
+    class HangClient:
+        @overload
+        async def chat_completions(
+            self, param: ChatCompletionsParam, *, stream: Literal[False] = False
+        ) -> ChatCompletionResponse: ...
+
+        @overload
+        async def chat_completions(
+            self, param: ChatCompletionsParam, *, stream: Literal[True]
+        ) -> AsyncIterator[ChatCompletionChunk]: ...
+
+        async def chat_completions(
+            self, param: ChatCompletionsParam, *, stream: bool = False
+        ) -> ChatCompletionResponse | AsyncIterator[ChatCompletionChunk]:
+            del param, stream
+            await asyncio.sleep(60)
+            return _response(AssistantChatMessage(content="never"))
+
+    agent = ChatAgent(HangClient(), model="m", memory=store, session_id=session.sid)
+    turn = asyncio.create_task(run_turn_with_retries(agent, starter=lambda: agent.run("cancel-me"), delays=()))
+    await asyncio.sleep(0.05)
+    _ = turn.cancel()  # first Ctrl+C: cancels the in-flight turn
+    ok = await turn  # must return False instead of raising KeyboardInterrupt
+    assert ok is False
+    assert agent.pending_retry_text == "cancel-me"
+    await store.close()
+
+
+async def test_second_ctrl_c_during_retry_cancel_message_stays_benign(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Regression: a second Ctrl+C during the retry-cancel message is benign."""
+
+    async def interrupted_sleep(_seconds: float) -> bool:
+        return False  # first Ctrl+C interrupted the retry wait
+
+    monkeypatch.setattr("plyngent.cli.retry.sleep_cancellable", interrupted_sleep)
+
+    calls: list[int] = [0]
+
+    def raiser(message: object = None, **kwargs: object) -> None:
+        calls[0] += 1
+        if calls[0] == 2:  # second Ctrl+C lands on the "auto-retry cancelled" line
+            raise KeyboardInterrupt
+
+    monkeypatch.setattr("plyngent.cli.retry.click.secho", raiser)
+
+    assert await _wait_for_retry(1, 3, 0.01) is False
+
+
+async def test_second_ctrl_c_during_retry_announce_stays_benign(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """A Ctrl+C during the "retrying" announcement does not abort the turn."""
+
+    async def ok_sleep(_seconds: float) -> bool:
+        return True
+
+    monkeypatch.setattr("plyngent.cli.retry.sleep_cancellable", ok_sleep)
+
+    calls: list[int] = [0]
+
+    def raiser(message: object = None, **kwargs: object) -> None:
+        calls[0] += 1
+        if calls[0] == 2:  # Ctrl+C lands on the "retrying" line
+            raise KeyboardInterrupt
+
+    monkeypatch.setattr("plyngent.cli.retry.click.secho", raiser)
+
+    assert await _wait_for_retry(1, 3, 0.01) is True
+
+
 async def test_manual_retry_after_exhausted(monkeypatch: pytest.MonkeyPatch) -> None:
     async def no_wait(_seconds: float) -> bool:
         return True