Brandt Bucher <brandtbuc...@gmail.com> added the comment:

I forgot to mention that I confirmed that the last passing test run used 18.04 
(click "set up job" -> "Operating System" to see):

https://github.com/python/cpython/runs/2013210763?check_suite_focus=true

The next one, which started the current chain of failures, used 20.04:

https://github.com/python/cpython/runs/2018900756?check_suite_focus=true

I'm still not sure *why* this broke CI, though. Perhaps our cached OpenSSL is 
no longer valid?

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