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If git uses curl, then switching to use curl to guess if command line git would block may avoid these self-signed certificate cases.
I'd love to see a pull request with that change proposed, including a set of automated tests to verify it is working correctly.
Currently, I'm working to create automated tests of some relatively simple authenticated access paths (https, ssh, github, bitbucket, local server, etc.). My tests won't check for a self-signed certificate initially, since I don't have a self-signed certificate installed on any of the git servers I use for testing.