msmtp on Debian

Tim Chase blinux.list at
Wed Apr 15 13:29:23 UTC 2015

I seem to recall that, by default TLS happens over the usual SMTP
port 25.  I've had multiple ISPs block outbound traffic on port 25
because it's often used by spammers.  You might try

  telnet 25

and see if that times out or actually connects.  If that's the case,
most mail-servers provide alternate ports for TLS/SSL connections.
Check your ~/.msmtprc file to see if you're specifying a port (should
be something like "port 465") that is unfiltered.  You can try the
above telnet command to test connecting to port 465.

Alternatively, if it's timing out legitimately, you can bump it up by
adding a line like

  timeout 60

where it's measured in seconds.  I don't know what your system
default is.  However, most hosts should respond reasonably in under
20 seconds, so if it's taking longer than that, I'd investigate other
issues first.


On April 15, 2015, John J. Boyer wrote:
> I have just installed Debian, and I'm using msmtp as the outgoing
> email client. When I send a message I get the error "TSL handshake
> failed. Operation timed out." The copyright date on this version is
> 2014. I also have a Vinux 4 installation that has an msmtp with a
> copyright date of 2011. This version works. Is there something that
> needs to be set in the configuration file for the 2014 version?
> Thanks,
> John
> John J. Boyer; President,
> AbilitiesSoft, Inc.
> Madison, Wisconsin USA
> We develop software for people with disabilities which is abailable
> at no cost.
> _______________________________________________
> Blinux-list mailing list
> Blinux-list at

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