From e2bb9fb7178291175f6208a75f01e216884b77ba Mon Sep 17 00:00:00 2001
From: banteg <4562643+banteg@users.noreply.github.com>
Date: Tue, 20 Jan 2026 13:23:07 +0400
Subject: [PATCH] fix: clear chat sessions on cwd change (#172)

---
 docs/how-to/chat-sessions.md         |  4 ++++
 src/takopi/telegram/chat_sessions.py | 17 +++++++++++++++
 src/takopi/telegram/loop.py          |  9 ++++++++
 tests/test_telegram_chat_sessions.py | 31 ++++++++++++++++++++++++++++
 4 files changed, 61 insertions(+)

diff --git a/docs/how-to/chat-sessions.md b/docs/how-to/chat-sessions.md
index 4be7644..c89fc9a 100644
--- a/docs/how-to/chat-sessions.md
+++ b/docs/how-to/chat-sessions.md
@@ -57,6 +57,10 @@ If you prefer a cleaner chat, hide resume lines:
 
 In group chats, Takopi stores a session per sender, so different people can work independently in the same chat.
 
+## Working directory changes
+
+When `session_mode = "chat"` is enabled, Takopi clears stored chat sessions on startup if the current working directory differs from the one recorded in `telegram_chat_sessions_state.json`. This avoids resuming directory-bound sessions from a different project.
+
 ## Related
 
 - [Conversation modes](../tutorials/conversation-modes.md)
diff --git a/src/takopi/telegram/chat_sessions.py b/src/takopi/telegram/chat_sessions.py
index 6acc1f2..8bba540 100644
--- a/src/takopi/telegram/chat_sessions.py
+++ b/src/takopi/telegram/chat_sessions.py
@@ -24,6 +24,7 @@ class _ChatState(msgspec.Struct, forbid_unknown_fields=False):
 
 class _ChatSessionsState(msgspec.Struct, forbid_unknown_fields=False):
     version: int
+    cwd: str | None = None
     chats: dict[str, _ChatState] = msgspec.field(default_factory=dict)
 
 
@@ -64,11 +65,27 @@ class ChatSessionStore(JsonStateStore[_ChatSessionsState]):
                 return None
             return ResumeToken(engine=engine, value=entry.resume)
 
+    async def sync_startup_cwd(self, cwd: Path) -> bool:
+        normalized = str(cwd.expanduser().resolve())
+        async with self._lock:
+            self._reload_locked_if_needed()
+            previous = self._state.cwd
+            cleared = False
+            if previous is not None and previous != normalized:
+                self._state.chats = {}
+                cleared = True
+            if previous != normalized:
+                self._state.cwd = normalized
+                self._save_locked()
+            return cleared
+
     async def set_session_resume(
         self, chat_id: int, owner_id: int | None, token: ResumeToken
     ) -> None:
         async with self._lock:
             self._reload_locked_if_needed()
+            if self._state.cwd is None:
+                self._state.cwd = str(Path.cwd().expanduser().resolve())
             chat = self._ensure_chat_locked(chat_id, owner_id)
             chat.sessions[token.engine] = _SessionState(resume=token.value)
             self._save_locked()
diff --git a/src/takopi/telegram/loop.py b/src/takopi/telegram/loop.py
index 73e537c..c32187e 100644
--- a/src/takopi/telegram/loop.py
+++ b/src/takopi/telegram/loop.py
@@ -3,6 +3,7 @@ from __future__ import annotations
 from collections.abc import AsyncIterator, Awaitable, Callable, Mapping
 from dataclasses import dataclass
 from functools import partial
+from pathlib import Path
 from typing import TYPE_CHECKING, cast
 
 import anyio
@@ -964,6 +965,14 @@ async def run_main_loop(
             state.chat_session_store = ChatSessionStore(
                 resolve_sessions_path(config_path)
             )
+            cleared = await state.chat_session_store.sync_startup_cwd(Path.cwd())
+            if cleared:
+                logger.info(
+                    "chat_sessions.cleared",
+                    reason="startup_cwd_changed",
+                    cwd=str(Path.cwd()),
+                    state_path=str(resolve_sessions_path(config_path)),
+                )
             logger.info(
                 "chat_sessions.enabled",
                 state_path=str(resolve_sessions_path(config_path)),
diff --git a/tests/test_telegram_chat_sessions.py b/tests/test_telegram_chat_sessions.py
index 5385222..7d81479 100644
--- a/tests/test_telegram_chat_sessions.py
+++ b/tests/test_telegram_chat_sessions.py
@@ -1,3 +1,5 @@
+from pathlib import Path
+
 import pytest
 
 from takopi.model import ResumeToken
@@ -36,3 +38,32 @@ async def test_chat_sessions_store_clear(tmp_path) -> None:
         engine="codex",
         value="two",
     )
+
+
+@pytest.mark.anyio
+async def test_chat_sessions_store_drops_sessions_on_cwd_change(
+    tmp_path, monkeypatch
+) -> None:
+    path = tmp_path / "telegram_chat_sessions_state.json"
+    dir1 = tmp_path / "dir1"
+    dir2 = tmp_path / "dir2"
+    dir1.mkdir()
+    dir2.mkdir()
+
+    monkeypatch.chdir(dir1)
+    store = ChatSessionStore(path)
+    await store.set_session_resume(1, None, ResumeToken(engine="codex", value="abc123"))
+    assert await store.get_session_resume(1, None, "codex") == ResumeToken(
+        engine="codex", value="abc123"
+    )
+
+    store2 = ChatSessionStore(path)
+    assert await store2.sync_startup_cwd(Path.cwd()) is False
+    assert await store2.get_session_resume(1, None, "codex") == ResumeToken(
+        engine="codex", value="abc123"
+    )
+
+    monkeypatch.chdir(dir2)
+    store3 = ChatSessionStore(path)
+    assert await store3.sync_startup_cwd(Path.cwd()) is True
+    assert await store3.get_session_resume(1, None, "codex") is None