diff --git a/hermes_cli/cli_commands_mixin.py b/hermes_cli/cli_commands_mixin.py
index 4e65155b602..8f9e6b8e886 100644
--- a/hermes_cli/cli_commands_mixin.py
+++ b/hermes_cli/cli_commands_mixin.py
@@ -834,6 +834,14 @@ class CLICommandsMixin:
         else:
             _cprint(f"  ↻ Resumed session {target_id}{title_part} — no messages, starting fresh.")
 
+        # Retarget the process + tool cwd to where the session was started, so a
+        # mid-chat /resume (and /sessions <id>, which delegates here) lands in the
+        # same directory as a startup `hermes -c`/`--resume`. The startup resume
+        # paths already call this; without it, the terminal/code-exec tools and
+        # relative-path resolution keep operating in the wrong repo. Idempotent
+        # and a no-op when the session recorded no cwd. See #38562.
+        self._restore_session_cwd(session_meta)
+
     def _handle_sessions_command(self, cmd_original: str) -> None:
         """Handle /sessions [list|<id_or_title>] — browse or resume previous sessions.