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I have smtp-server=mail.domain1.tld:587/user=user1@domain2.tld/ssl in my .pinerc.

When I try to send, alpine 2.21 complains SSL negotiation failed and suggests that I add 'notls' to the server name. Of course, that will not work as the server requires secure connections.

I can connect to the same server:port and account from the same machine using other mail clients. I can connect to the IMAP store with alpine with no problem using inbox-path={mail.domain1.tld:993/user=user1@domain2.tld/ssl}

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I had a similar problem, but solved it by changing from

mail.domain1.tld:587/user=user1@domain2.tld/ssl

to:

mail.domain1.tld:587/tls/user=user1@domain2.tld

The top syntax can work for smtpd_tls_wrapper_mode usually running on port 465. I think it has to do with a STARTTLS command not being issued by pine in the first way of writing but Im not sure.

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The solution seems to be "use mutt", which seems to understand IMAP/Submission much better than alpine, so that's what I've done. No problems.

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    I'm glad you're functional again, although I struggle to see this as a "solution" to the listed Alpine question. – Jeff Schaller Sep 17 '17 at 11:54
  • It's only a "solution" in that it closes the question as there doesn't seem to be a good answer. Mutt works well with secure submission and alpine does not. – lbutlr Sep 18 '17 at 2:58

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