On 02 Jul 2013, at 20:01, Noel <[email protected]> wrote:

> This is unlikely to work on port 587, since monit (AFAIK) won't send STARTTLS 
> to initiate the TLS session.

Actually Monit will send STARTTLS if 'use tlsv1' is specified. Other tips might 
be to first check that Monit is compiled with openssl (ldd monit). 

Also if port 465 is used you should try 'use sslv3' rather than tls. 
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