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Since version >= 1.8.0 using OpenSSL is discouraged, from NEWS: - Using OpenSSL is discouraged and may not be supported in the future. Please use GnuTLS instead. The reasons are explained here: https://marlam.de/msmtp/news/openssl-discouraged/ The linked website states that: I don't work on it myself anymore, and the last time somebody sent a patch was 8 years ago. We don't want to depend on unmaintained code pieces for TLS support.