I believe I figured out the issue, at least on the master branch.

While checking the certificates used by asyncio tests within the test_asyncio folder I noticed they were quite outdated when compared to the more recent updated ones with the test/ folder, which take into account the stronger crypto defaults introduced in the latest openssl versions.

And by looking at https://github.com/python/cpython/commit/6d8c1abb003a4cb05f1ddcf0eeddeeeed513cd57#diff-a8e7dbb528601706db0f01d01332bb76 it seems that those certs are just copied from test/ within test_asyncio/. So by copying over the old certs, the tests actually pass.

The immediate workaround would be to just copy over the certs but a better approach would be to just reuse the certs within the test/ folder instead of relying on copying them over to test_asyncio/