diff --git a/tests/cli/test_cli_resume_command.py b/tests/cli/test_cli_resume_command.py
index 299d5fad273c..de2c0fe639be 100644
--- a/tests/cli/test_cli_resume_command.py
+++ b/tests/cli/test_cli_resume_command.py
@@ -1,3 +1,4 @@
+import os
 from types import SimpleNamespace
 from unittest.mock import MagicMock, patch
 
@@ -153,6 +154,78 @@ class TestCliResumeCommand:
         assert "<half" in printed
 
 
+class TestCliResumeRestoresCwd:
+    """Mid-chat /resume must retarget the working directory to where the
+    session was started — the same contract as a startup ``hermes -c`` /
+    ``--resume``.
+
+    Regression coverage for #38562: ``_restore_session_cwd()`` was wired into
+    the startup resume paths but not into ``_handle_resume_command()``, so an
+    interactive ``/resume`` (and ``/sessions <id>``, which delegates here) left
+    the process + ``TERMINAL_CWD`` pointing at whatever directory the user had
+    cd'd into — so the terminal/code-exec tools and relative paths ran in the
+    wrong repo.
+    """
+
+    def _resumable_cli(self, session_meta):
+        cli_obj = _make_cli()
+        cli_obj._session_db.get_session.return_value = session_meta
+        cli_obj._session_db.get_messages_as_conversation.return_value = [
+            {"role": "user", "content": "hello"},
+        ]
+        cli_obj._session_db.resolve_resume_session_id.return_value = session_meta["id"]
+        return cli_obj
+
+    def test_handle_resume_restores_recorded_cwd(self, tmp_path):
+        recorded = str(tmp_path)
+        cli_obj = self._resumable_cli({"id": "sess_dir", "title": "Dir", "cwd": recorded})
+
+        with (
+            patch("hermes_cli.main._resolve_session_by_name_or_id", return_value="sess_dir"),
+            patch("cli._cprint"),
+            patch.object(cli_obj, "_console_print"),
+            patch("os.chdir") as mock_chdir,
+            patch.dict(os.environ, {}, clear=False),
+        ):
+            cli_obj._handle_resume_command("/resume Dir")
+            # Assert inside the patch.dict scope — it restores os.environ on exit.
+            assert os.environ.get("TERMINAL_CWD") == recorded
+
+        mock_chdir.assert_called_once_with(recorded)
+
+    def test_handle_resume_without_recorded_cwd_does_not_chdir(self):
+        # Gateway/remote/older sessions record no cwd — restore must no-op.
+        cli_obj = self._resumable_cli({"id": "sess_dir", "title": "Dir"})
+
+        with (
+            patch("hermes_cli.main._resolve_session_by_name_or_id", return_value="sess_dir"),
+            patch("cli._cprint"),
+            patch.object(cli_obj, "_console_print"),
+            patch("os.chdir") as mock_chdir,
+        ):
+            cli_obj._handle_resume_command("/resume Dir")
+
+        mock_chdir.assert_not_called()
+
+    def test_sessions_command_restores_recorded_cwd(self, tmp_path):
+        # /sessions <id> delegates to the resume flow, so it restores cwd too.
+        recorded = str(tmp_path)
+        cli_obj = self._resumable_cli({"id": "sess_dir", "title": "Dir", "cwd": recorded})
+
+        with (
+            patch("hermes_cli.main._resolve_session_by_name_or_id", return_value="sess_dir"),
+            patch("cli._cprint"),
+            patch.object(cli_obj, "_console_print"),
+            patch("os.chdir") as mock_chdir,
+            patch.dict(os.environ, {}, clear=False),
+        ):
+            cli_obj._handle_sessions_command("/sessions Dir")
+            # Assert inside the patch.dict scope — it restores os.environ on exit.
+            assert os.environ.get("TERMINAL_CWD") == recorded
+
+        mock_chdir.assert_called_once_with(recorded)
+
+
 class TestPendingResumeNumberedSelection:
     """Bare `/resume` arms a one-shot prompt so the next bare number resumes.