I ran into a similar problem with my hosted e-mail provider, and there are a couple of things that helped me:

1) The smtp host name (the one returned by "telnet server 25") was the only one that would work for my authentication step. 2) Some providers use alternate ports for anything by "vanilla" e-mail forwarding.

You might also want to check with your SMTP provider - they may not let you do this at all.....

Dave

On 5/9/2012 10:36 AM, Scott Sjodin wrote:
Kevin,

I'm using an external mail server that's hosted, so I can't exactly check those logs. I will check out the verbose logging and the client you suggested and report back. Thank You.

On Wed, May 9, 2012 at 7:17 PM, Kevin Falcone <[email protected] <mailto:[email protected]>> wrote:

    On Wed, May 09, 2012 at 07:13:24PM +0400, Scott Sjodin wrote:
    > Msmtp is running, however, when I attempt to send mail thru a
    test (msmtp
    > -a default <username>@domain.com <http://domain.com>) I get the
    following errors both in the
    > CLI and the log:
    >
    > msmtp: TLS handshake failed: the operation timed out
    > msmtp: could not send mail (account default from /etc/msmtprc)

    If msmtp has a verbose mode, use it.  Otherwise, your best bet is
    going to be the logs of the server you're trying to relay through.

    You can also use openssl's s_client command to try connecting to the
    relay server to check the tls connection.

    -kevin




--
Dave Burgess
Manager
Cynjut Consulting Services, LLC
402-403-4434 (Phone, FAX, and Cell)


--
Dave Burgess - Manager VOIP Nebraska 402-403-4434 (Phone, FAX, and Cell) /A subsidiary of Cynjut Consulting Svcs, LLC/

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