chore: improve OpenSandbox maintenance path

[lphuc2250gma]

Summary:

• Add or tighten focused edge-case tests or type assertions in cli/tests/conftest.py, cli/tests/test_utils.py related to Python typing, tests, CLI ergonomics, observability; avoid docs-only changes and broad refactors.
• Keep the change narrow so it is straightforward to review.

Notes:

• I kept this scoped to the relevant implementation and tests.

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Changed directories: cli.

💡 Tip: Use feature for new functionality or improvements, bug for fixes.

cc @lphuc2250gma