Msmtp with RT 4.0.5 setup issues

Hi all,

Thanks to this community, I almost have RT fully up and operational.

The last step is getting msmtp to work. I’m not sure what’s wrong and in
troubleshooting haven’t gotten very far. As a guideline, I followed this
wiki page for instructions: http://requesttracker.wikia.com/wiki/Msmtp. I’m
using the default msmtprc file to simplify things.

Msmtp is running, however, when I attempt to send mail thru a test (msmtp
-a default @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)

For reference, my msmtprc file looks like this:

defaults
logfile /var/log/msmtp.log
account default
host smtp.mydomain.com
port 587
tls on
tls_certcheck off
tls_starttls off
auth on
user username@domain.com
password suparsekratpw
from username@domain.com
password suparsekratpw
auto_from on

Anybody have any tips or pointers? It would be greatly appreciated. Thanks
in advance.

Scott

Msmtp is running, however, when I attempt to send mail thru a test (msmtp
-a default @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

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 falcone@bestpractical.comwrote:

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 @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

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…

DaveOn 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 <falcone@bestpractical.com mailto:falcone@bestpractical.com> 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/