ssmtp - possible anomaly with SSL

[Chris Brennan]

On Sat, Nov 6, 2010 at 12:50 PM, Steven Friedrich <FreeBSD at insightbb.com>wrote:

> On Saturday 06 November 2010 12:01:53 pm Chad Perrin wrote:
> > On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote:
> > > I recently figured out how to send mail thru my ISP ID using ssmtp.  I
> > > had previously only been using KMail, and I had it configured to use
> > > port 465  SSL LOGIN.
> > >
> > > I can send mail when I don't use port 465:
> > > mailhub=mail.InsightBB.com
> > >
> > > but if I add the port 465 a,d enable SSL with:
> > > UseTLS=YES
> > >
> > > then I use the -v switch and also -auFreeBSD -apPassword
> > > as in smtp -v -auFreeBSD -apPassword freebsd at insightbb.com
> > >
> > > and the messages all indicate success, but the mail never arrives. It
> > > does when I don't use SSL on port 465.
> > >
> > > KMail does work with SSL on port 465.
> >
> > I'm not entirely clear on what you're using as a mail user agent.  Are
> > you still using KMail as your MUA, but using ssmtp to send the emails to
> > your SMTP server, or have you switched MUAs when you started using ssmtp?
> >
> > Chris Brennan suggested you send more information; in addition to
> > answering my question, it might be useful to give us the information
> > Chris requested -- but make sure you obscure any username/password
> > information.
>
> I still use KMail for my essential email.
>
> However, I want to be able to use send-pr.  There is a  port called  ssmtp,
> and I use it only for outgoing mail, it allows any userID to send outgoing
> email using a single ISP account.
>
> When my /usr/local/etc/ssmtp.conf is:
> root=FreeBSD at InsightBB.com
> mailhub=mail.InsightBB.com
> rewriteDomain=InsightBB.com
> hostname=_HOSTNAME_
>
> I can send an outgoing email to myself so I can prove it works.
> ssmtp -v freebsd at insighttbb.com
>
> 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 InsightBB.com
> mailhub=mail.InsightBB.com:465
> rewriteDomain=InsightBB.com
> 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...
> --
> System Name:   laptop2.StevenFriedrich.org
> Hardware:      2.80GHz Intel Pentium 4 (HTT) with 2 GB memory
> OS version:    FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel)
> manager(s):    kde4-4.5.3
> X windows:     xorg-7.5    X.Org X Server 1.7.5
> _______________________________________________
>

/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.