This might be because your server is asking for client certs and supplying an [long] list of acceptable CA's. And your msmtp may be linked to openssl libs which interprets that. And msmtp appears to be considering something therein an error instead of continuing with the session as raw gnutls/openssl clients would. Or you're genuinely timing out. See: - ldd msmtp - openssl s_client -connect mail.smart-cactus.org:587 -starttls smtp -showcerts -msg -debug [Acceptable client certificate CA names] [...]
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