diff --git a/cli.py b/cli.py
index 97698f133d08..2964455f9dbd 100644
--- a/cli.py
+++ b/cli.py
@@ -396,14 +396,26 @@ def load_cli_config() -> Dict[str, Any]:
     if "backend" in terminal_config:
         terminal_config["env_type"] = terminal_config["backend"]
     
-    # Handle special cwd values: "." or "auto" means use current working directory.
-    # Only resolve to the host's CWD for the local backend where the host
-    # filesystem is directly accessible.  For ALL remote/container backends
-    # (ssh, docker, modal, singularity), the host path doesn't exist on the
-    # target -- remove the key so terminal_tool.py uses its per-backend default.
+    # Handle special cwd values: "." or "auto" means use a concrete working
+    # directory. For local backends, prefer an already-established TERMINAL_CWD
+    # (e.g. set by gateway/run.py from MESSAGING_CWD) so we do not clobber the
+    # gateway's workspace with os.getcwd(). For remote/container backends,
+    # remove the key so terminal_tool.py uses its per-backend default.
     if terminal_config.get("cwd") in (".", "auto", "cwd"):
         effective_backend = terminal_config.get("env_type", "local")
-        if effective_backend == "local":
+        existing_terminal_cwd = os.environ.get("TERMINAL_CWD", "").strip()
+        if effective_backend == "local" and existing_terminal_cwd:
+            try:
+                if Path(existing_terminal_cwd).expanduser().is_dir():
+                    terminal_config["cwd"] = existing_terminal_cwd
+                    defaults["terminal"]["cwd"] = existing_terminal_cwd
+                else:
+                    terminal_config["cwd"] = os.getcwd()
+                    defaults["terminal"]["cwd"] = terminal_config["cwd"]
+            except OSError:
+                terminal_config["cwd"] = os.getcwd()
+                defaults["terminal"]["cwd"] = terminal_config["cwd"]
+        elif effective_backend == "local":
             terminal_config["cwd"] = os.getcwd()
             defaults["terminal"]["cwd"] = terminal_config["cwd"]
         else:
diff --git a/tests/cli/test_cli_init.py b/tests/cli/test_cli_init.py
index b926d55f535d..b09a20176036 100644
--- a/tests/cli/test_cli_init.py
+++ b/tests/cli/test_cli_init.py
@@ -331,6 +331,54 @@ def test_normalize_root_model_keys_does_not_override_existing(self):
         assert "provider" not in result  # root key still cleaned up
 
 
+class TestTerminalCwdPrecedence:
+    """load_cli_config() should respect an already-set TERMINAL_CWD."""
+
+    def test_existing_terminal_cwd_wins_over_dot_cwd(self, tmp_path, monkeypatch):
+        import yaml
+        import cli
+
+        hermes_home = tmp_path / ".hermes"
+        hermes_home.mkdir()
+        config_path = hermes_home / "config.yaml"
+        config_path.write_text(yaml.safe_dump({"terminal": {"env_type": "local", "cwd": "."}}))
+
+        workspace = tmp_path / "messaging-workspace"
+        workspace.mkdir()
+        system_cwd = tmp_path / "systemd-working-dir"
+        system_cwd.mkdir()
+
+        monkeypatch.setattr(cli, "_hermes_home", hermes_home)
+        monkeypatch.setenv("TERMINAL_CWD", str(workspace))
+        monkeypatch.chdir(system_cwd)
+
+        cfg = cli.load_cli_config()
+
+        assert cfg["terminal"]["cwd"] == str(workspace)
+        assert os.environ["TERMINAL_CWD"] == str(workspace)
+
+    def test_missing_terminal_cwd_falls_back_to_os_cwd(self, tmp_path, monkeypatch):
+        import yaml
+        import cli
+
+        hermes_home = tmp_path / ".hermes"
+        hermes_home.mkdir()
+        config_path = hermes_home / "config.yaml"
+        config_path.write_text(yaml.safe_dump({"terminal": {"env_type": "local", "cwd": "."}}))
+
+        system_cwd = tmp_path / "systemd-working-dir"
+        system_cwd.mkdir()
+
+        monkeypatch.setattr(cli, "_hermes_home", hermes_home)
+        monkeypatch.delenv("TERMINAL_CWD", raising=False)
+        monkeypatch.chdir(system_cwd)
+
+        cfg = cli.load_cli_config()
+
+        assert cfg["terminal"]["cwd"] == str(system_cwd)
+        assert os.environ["TERMINAL_CWD"] == str(system_cwd)
+
+
 class TestProviderResolution:
     def test_api_key_is_string_or_none(self):
         cli = _make_cli()