I have been looking at Alpine the last few days. Thunderbird has been serving me great but I want to give a console based email client a try again, just like in the old days.

My Thunderbird was setup to submit mail over SSL/TLS to port 465 of SMTP server. Looking at the alpine documentation did not really give any helpful clues on how to configure this. Searching on the web did get me a few references of people using TLS with port 465.

The examples I found did not work for me but after a few experiments I was able to get a working solution. Instead of configuring tls I had to configure ssl.

Not working

smtp-server=smtp.example.com:465/tls/user=yourname@example.com

Working

smtp-server=smtp.example.com:465/ssl/user=yourname@example.com

By the way if you need to submit SMTP mail over port 587 (which uses STARTTLS) use a configuration like:

smtp.example.com:587/tls/user=yourname@example.com

Only after I solved the issue I found the following explanation in the BSD ports help (I lost the link).

Modify the setting for "SMTP Server (for sending)" as follows:

    smtp.example.com:port/qualifier/user=user@example.com

where:
    - smtp.example.com is the fully qualified server name
    - port is the smtp server port
    - qualifier is something like ssl or tls (add /novalidate-cert when
      using a self-signed certificate)
    - user@example.com is your email address

Only remember when to use ssl and when to use tls. Hope this helps someone.

Alpine