ssmtp - possible anomaly with SSL

[Steven Friedrich]

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