[Dovecot] STARTTLS does not seem to work

[Phil Howard]

On Mon, May 24, 2010 at 17:31, Mike Abbott <michael.abbott at apple.com> wrote:
>> Well, that kinda complicates a "STARTTLS tunnel"
>
> Perhaps you might be interested in these commands.  I'm not sure about their portability but they work tolerably well in scripts on Mac OS X 10.6.
>
> $ openssl s_client -connect yourhost:imap -starttls imap
> $ openssl s_client -connect yourhost:pop3 -starttls pop3
>
> $ openssl s_client -connect yourhost:imaps
> $ openssl s_client -connect yourhost:pop3s
>
> $ openssl s_client -connect yourhost:smtp -starttls smtp
>

Yeah, that can be used, perhaps best with expect or pexpect.  I'm
hoping to find tools that can do basic email functions at a higher
level, where the user of the tool does not need to know the protocol
details, but only needs to consider the same kinds of configuration
aspects that configuring a regular email client involves (except
without all the misleading and often erroneous terminology used by
these GUI client developers ... such as "TLS" for STARTTLS/STLS on
clear ports, and "SSL" for wrapped/tunneled TLS/SSL connections on
always-encrypted ports as used in Evolution).

At some point I think I need to learn the OpenSSL library API for C so
I can write some command line tool apps of my own with it (now we're
getting well off the Dovecot topic).