ssmtp - possible anomaly with SSL

Chad Perrin perrin at
Sat Nov 6 20:21:20 UTC 2010

On Sat, Nov 06, 2010 at 12:54:39PM -0400, Chris Brennan wrote:
> On Sat, Nov 6, 2010 at 12:50 PM, Steven Friedrich <FreeBSD at>wrote:
> >
> > I still use KMail for my essential email.

Okay, thanks for clarifying, Steven.

> >
> > And the verbose output indicates success. I didn't post it, just stated
> > what
> > it was.
> >
> > But when I configure SSL on port 465, it also shows a good exchange, but
> > maybe I didn't wait long enough to see it get thru the ISP's system.
> >
> > So my SSL version of ssmtp.conf is:
> > root=FreeBSD at
> >
> >
> > hostname=_HOSTNAME_
> > # Use SSL/TLS to send secure messages to server.
> > UseTLS=YES
> >
> > The verbose option indicated success  when sending an email from
> > root.  Let me verify that it wasn't my mistake for not waiting
> > longer...

. . . and you said that setting it to send email through in KMail config works.  Right?

In addition to Chris Brennan's article references, there's another that I
wrote quite some time ago that I think explains ssmtp config for TLS use
pretty well:

From what you said so far, it seems like ssmtp is configured correctly.
It seems likely, then, that the problem is with KMail or with something
filtering port 465.  Does KDE have something going on with firewall
management that might be allowing KMail to send stuff on port 465 while
outside of KDE's "help" you cannot?  Have you checked to see whether you
can send with your TLS settings for ssmtp from outside of KMail?

If you are not wedded to ssmtp per se, you could always try msmtp

It does much the same sort of stuff as ssmtp, but is a bit more "feature
rich", and appears to be more actively maintained than ssmtp.

> /var/log/maillog is where you will see success/fail. Your config looks good
> to me, so I would watch maillog while sending mail and see what crops up.

It appears that Chris Brennan knows a bit about this subject.  Yes, that
file may prove useful in troubleshooting this issue.  If you are having
trouble figuring out whether maillog has anything to offer for hints, you
might want to paste its contents into pastebin and give us a link to it
there so we can give it a look (after checking to make sure you are not
pasting any sensitive data, of course).

Chad Perrin [ original content licensed OWL: ]
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