ssmtp - possible anomaly with SSL

Steven Friedrich FreeBSD at
Sat Nov 6 16:50:26 UTC 2010

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:
> >
> > 
> > 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
> > 
> > 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                                                                

I can send an outgoing email to myself so I can prove it works.
ssmtp -v freebsd at

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                                                                
# Use SSL/TLS to send secure messages to server.

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:
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

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