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That's a connection reset error which usually means that something along the network path, either a proxy/firewall or the target server actively closed the connection.
Check that calibre is not picking up any proxies by going to Preferences->Miscellaneous where it should say "No proxies used"
Other than that, I dont have any suggestions. Note that calibre comes with its own python/openssl libraries so updating system ones has no effect one way or the other.
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