in reply to SMTP and TLS

After a little investigation I believe that the problem is likely that the Amazon server is not greeting with a 220 welcome message (as you can see from the telnet session (in orig post) that it doesn't send one). So my clients are hanging, waiting for the response.

I suppose the best solution (if I want to stick with Amazon) is to modify one of these clients. *sigh*

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Re^2: SMTP and TLS
by Rodster001 (Pilgrim) on Jan 27, 2012 at 18:57 UTC
    I ended up configuring sendmail to work with Amazon's SES

    First set up a secure tunnel
    http://docs.amazonwebservices.com/ses/latest/DeveloperGuide/SMTP.MTAs.SecureTunnel.html

    And then configure sendmail
    http://docs.amazonwebservices.com/ses/latest/DeveloperGuide/SMTP.MTAs.Sendmail.html

    Then I can just use Mail::Sender again. This set up seems to work nicely. I hate not being able to resolve the exact problem (above) but I need to move onto other things :)