ImportError: /root/.local/share/letsencrypt/local/lib/python2.7/dist-packages/cryptography/hazmat/bindings/_openssl.so: undefined symbol: OPENSSL_sk_num
From what I gather letsencrypt does not support latest OpenSSL
Could be, but looking at the specific error it could be that it will be fixed if you recompile cryptography.
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@iroiban I believe if you search the Certbot issues page there have been other similar reports that were fixed once the headers & installed OpenSSL version are in-sync. You might have luck searching those issues for a way to do what @osiris suggests.
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