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Ubuntu 20.04 comes with a patched OpenSSL 1.1.1. Default security level 2 blocks TLS 1.0 and 1.1 connections. Regular OpenSSL 1.1.1 builds allow TLS 1.0 and 1.1 on security level 2. See: See: https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1899878 See: https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1917625 Signed-off-by: Christian Heimes <christian@python.org> (cherry picked from commit f6c6b5821bff815bdc810de53992fd1fbdb2edd4) Co-authored-by: Christian Heimes <christian@python.org>