On Wed, Nov 09, 2005 at 08:38:02PM -0500, Warrick FitzGerald wrote:

> Hi Guys,
> 
> I'm trying to test a connection to a TLS enabled SMTP server. Is it
> possible to use use OpenSSL to setup the TLS sessison and then interact
> with the mail server as if I'd telnet'd to port 25?
> 

Yes, with significant limitations via "openssl s_client". For full
interactive TLS you can use stunnel which supports SMTP.

The problems with s_client are:

    - It does not send EHLO, and many servers refuse STARTTLS before EHLO.

    - It is a debugging tool, not a proxy, so "R" causes renegotiation, and
    literal "R" cannot be sent, ...

-- 
        Viktor.
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