diff --git a/tests/tools/test_terminal_task_cwd.py b/tests/tools/test_terminal_task_cwd.py
index 85817fa53..009e3f7e0 100644
--- a/tests/tools/test_terminal_task_cwd.py
+++ b/tests/tools/test_terminal_task_cwd.py
@@ -223,6 +223,89 @@ def test_registering_non_cwd_override_leaves_live_env_cwd_untouched(monkeypatch)
     assert fake_env.cwd == "/workspace/keep"
 
 
+def test_stale_env_cwd_from_different_session_is_ignored(monkeypatch):
+    """A different session's `cd` left env.cwd pointing at its checkout.
+
+    The terminal env is shared (collapsed to "default"), so env.cwd tracks the
+    LAST session that ran a command.  When session B claims the env after
+    session A left it in A's worktree, the first command must NOT run in A's
+    leftover cwd — it must fall through to the config/override cwd (this
+    session's own workspace).
+    """
+    calls = []
+
+    class FakeEnv:
+        env = {}
+        cwd = "/home/user/src/hermes-desktop-tipc/apps/desktop"
+        cwd_owner = "session-A-key"
+
+        def execute(self, command, **kwargs):
+            calls.append((command, kwargs))
+            return {"output": "ok", "returncode": 0}
+
+    task_id = "session-B"
+    monkeypatch.setattr(terminal_tool, "_active_environments", {"default": FakeEnv()})
+    monkeypatch.setattr(terminal_tool, "_last_activity", {})
+    monkeypatch.setattr(terminal_tool, "_task_env_overrides", {})
+    monkeypatch.setattr(terminal_tool, "_get_env_config", lambda: _minimal_terminal_config(cwd="/home/user/src/hermes-agent"))
+    monkeypatch.setattr(terminal_tool, "_start_cleanup_thread", lambda: None)
+    monkeypatch.setattr(terminal_tool, "_resolve_container_task_id", lambda value: "default")
+    monkeypatch.setattr(
+        terminal_tool,
+        "_check_all_guards",
+        lambda command, env_type, **kwargs: {"approved": True},
+    )
+
+    result = json.loads(terminal_tool.terminal_tool(command="pwd", task_id=task_id))
+
+    assert result["exit_code"] == 0
+    # The command must run in the config cwd (hermes-agent), NOT the stale
+    # env.cwd left by session A (hermes-desktop-tipc).
+    assert calls == [("pwd", {"timeout": 60, "cwd": "/home/user/src/hermes-agent"})]
+
+
+def test_same_session_env_cwd_is_trusted_after_first_claim(monkeypatch):
+    """Once a session has claimed the env, subsequent commands trust env.cwd.
+
+    The prev_owner check only rejects env.cwd when a DIFFERENT session owned it
+    before this call.  After the first command (which claims ownership),
+    subsequent calls in the same session should trust the live env.cwd so that
+    in-session `cd` state survives.
+    """
+    calls = []
+
+    class FakeEnv:
+        env = {}
+        cwd = "/workspace/deep"
+        cwd_owner = "session-X"
+
+        def execute(self, command, **kwargs):
+            calls.append((command, kwargs))
+            return {"output": "ok", "returncode": 0}
+
+    env = FakeEnv()
+    task_id = "session-X"
+    monkeypatch.setattr(terminal_tool, "_active_environments", {"default": env})
+    monkeypatch.setattr(terminal_tool, "_last_activity", {})
+    monkeypatch.setattr(terminal_tool, "_task_env_overrides", {})
+    monkeypatch.setattr(terminal_tool, "_get_env_config", lambda: _minimal_terminal_config(cwd="/workspace/config"))
+    monkeypatch.setattr(terminal_tool, "_start_cleanup_thread", lambda: None)
+    monkeypatch.setattr(terminal_tool, "_resolve_container_task_id", lambda value: "default")
+    monkeypatch.setattr(
+        terminal_tool,
+        "_check_all_guards",
+        lambda command, env_type, **kwargs: {"approved": True},
+    )
+
+    # First call: env was owned by "session-X" (same session_key since
+    # get_current_session_key falls back to task_id). prev_owner == current
+    # session, so env.cwd is trusted.
+    result = json.loads(terminal_tool.terminal_tool(command="pwd", task_id=task_id))
+
+    assert result["exit_code"] == 0
+    assert calls == [("pwd", {"timeout": 60, "cwd": "/workspace/deep"})]
+
+
 def test_safe_getcwd_returns_real_cwd(monkeypatch):
     monkeypatch.setattr(terminal_tool.os, "getcwd", lambda: "/home/user/project")
     assert terminal_tool._safe_getcwd() == "/home/user/project"
diff --git a/tools/terminal_tool.py b/tools/terminal_tool.py
index fc13367eb..692aa1e4a 100644
--- a/tools/terminal_tool.py
+++ b/tools/terminal_tool.py
@@ -1988,6 +1988,7 @@ def _resolve_command_cwd(
     workdir: Optional[str],
     env: Any,
     default_cwd: str,
+    prev_owner: Optional[str] = None,
 ) -> str:
     """Return the cwd for a command, preferring the live session cwd.
 
@@ -1996,12 +1997,29 @@ def _resolve_command_cwd(
     new directory in ``env.cwd``, but foreground/background calls kept forcing
     the old cwd back through ``env.execute(..., cwd=...)``. Explicit
     ``workdir=`` must still override everything.
+
+    When ``prev_owner`` is provided and differs from the current session,
+    ``env.cwd`` was mutated by a *different* session's ``cd`` and must NOT be
+    trusted — fall through to ``default_cwd`` (the config/override cwd) so
+    the command runs in this session's own workspace, not the previous
+    session's leftover checkout.  This mirrors the ``_live_cwd_if_owned``
+    guard file_tools uses for the same shared-env problem.
     """
     if workdir:
         return workdir
 
     live_cwd = getattr(env, "cwd", None)
     if isinstance(live_cwd, str) and live_cwd.strip():
+        # The env is shared (collapsed to "default"); its cwd tracks the LAST
+        # session that ran a command.  If a different session owned the env
+        # before this call claimed it, env.cwd is that session's leftover `cd`
+        # — not ours.  Don't use it.
+        if prev_owner is not None:
+            session_key = getattr(env, "cwd_owner", "")
+            # cwd_owner was already overwritten to the current session at the
+            # call site, so compare against the captured previous owner.
+            if prev_owner and prev_owner != "default" and session_key != prev_owner:
+                return default_cwd
         return live_cwd
 
     return default_cwd
@@ -2354,6 +2372,10 @@ def terminal_tool(
         from tools.approval import get_current_session_key
 
         session_key = get_current_session_key(default="") or (task_id or "")
+        # Capture the env's previous owner BEFORE claiming it — _resolve_command_cwd
+        # needs to know whether env.cwd was left by a *different* session's `cd`
+        # (in which case it's stale for this session and must be ignored).
+        prev_cwd_owner = getattr(env, "cwd_owner", "") or ""
         try:
             env.cwd_owner = session_key
         except Exception:
@@ -2369,6 +2391,7 @@ def terminal_tool(
                 workdir=workdir,
                 env=env,
                 default_cwd=cwd,
+                prev_owner=prev_cwd_owner,
             )
             try:
                 if env_type == "local":
@@ -2629,6 +2652,7 @@ def terminal_tool(
                         workdir=workdir,
                         env=env,
                         default_cwd=cwd,
+                        prev_owner=prev_cwd_owner,
                     )
                     execute_kwargs = {
                         "timeout": effective_timeout,