To my best knowledge

1. On startup, call a function to check the latest version from GitHub or a URL where version info is served.
   Example: https://api.github.com/repos/ozkanpakdil/swaggerific/releases/latest

2. If there’s a new version, ask the user to update (Y/n).

3. If user hit Y, download the zip and overwrite the current install.

   • If it’s a native exe, overwriting may fail (especially on Windows).
   • In that case, trigger a bash script to handle download + overwrite.

4. Be careful about the path the CLI needs correct access to write there.

5. Restart the CLI with the same parameters so it continues what the user requested.

   • CLI updated itself, user request runs, happy end.

I saw this flow in 2009 in a windows application. If you have MSI to deliver this may change but steps will be similar. Here there are many different examples.