diff --git a/litellm/proxy/client/cli/commands/claude_settings.py b/litellm/proxy/client/cli/commands/claude_settings.py
index 7e96d2a3a08..793728b0350 100644
--- a/litellm/proxy/client/cli/commands/claude_settings.py
+++ b/litellm/proxy/client/cli/commands/claude_settings.py
@@ -66,7 +66,7 @@ def claude_settings_path(environ: Mapping[str, str]) -> Path:
 
 def settings_file_owners(settings_path: Path) -> tuple[SettingsFileOwner, ...]:
     """The commands whose backups guard settings_path: `lite up` and `lite autoroute up` only ever manage the default file."""
-    return SETTINGS_FILE_OWNERS if settings_path == CLAUDE_SETTINGS_PATH else ()
+    return SETTINGS_FILE_OWNERS if settings_path.resolve() == CLAUDE_SETTINGS_PATH.resolve() else ()
 
 
 def load_json_or_empty(path: Path) -> dict[str, JsonValue]:
diff --git a/tests/test_litellm/proxy/client/cli/test_auth_commands.py b/tests/test_litellm/proxy/client/cli/test_auth_commands.py
index 9c3c02a5e85..d3e6d8f66ef 100644
--- a/tests/test_litellm/proxy/client/cli/test_auth_commands.py
+++ b/tests/test_litellm/proxy/client/cli/test_auth_commands.py
@@ -1477,6 +1477,21 @@ class TestLoginConfigClaude:
         assert "Run `lite down` first" in result.output
         assert not default_settings_path.exists()
 
+    def test_flag_refuses_while_lite_up_holds_the_default_file_reached_through_a_symlinked_config_dir(self, tmp_path):
+        default_config_dir = tmp_path / "default-home" / ".claude"
+        default_config_dir.mkdir(parents=True)
+        alias = tmp_path / "claude-alias"
+        alias.symlink_to(default_config_dir, target_is_directory=True)
+        (tmp_path / "claude_settings_backup.json").write_text("{}")
+
+        result, _settings_path, _backup_path = self._run_login(
+            tmp_path, ["--config-claude"], config_dir_env={"CLAUDE_CONFIG_DIR": str(alias)}
+        )
+
+        assert result.exit_code != 0
+        assert "`lite up` is currently managing" in result.output
+        assert not (default_config_dir / "settings.json").exists()
+
     def test_flag_writes_an_alternate_config_dir_even_while_lite_up_holds_the_default_file(self, tmp_path):
         (tmp_path / "claude_settings_backup.json").write_text("{}")