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I agree completely Jim. The problem is that OpenSSL regularly discovers face-meltingly bad security bugs, so it frequently pulls the "security exception" lever.
As with so many things in this life, we play the hand we're dealt. I have my fingers crossed that LibreSSL will, in the long run, be far more sane, and that we can switch to it someday. But for now I expect to have plenty more "necessary" OpenSSL upgrades foisted onto Python.