From owner-freebsd-questions@FreeBSD.ORG  Sat Sep  6 22:30:50 2003
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Date: Sat, 6 Sep 2003 22:30:46 -0700
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From: Doug Hardie <bc979@lafn.org>
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Subject: Use of Outlook Express with sendmail with SASL and TLS
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I started out with vanilla sendmail and then added SASL using LOGIN 
authentication.  That works fine.  I have configured Outlook Express 
5.0 on Win 98 and it authenticates fine.  It also works with Mac's mail 
app.  Then I added STARTTLS to sendmail.  That also works fine with 
Mac's mail app.  Just checked use SSL and tcpdump shows the packets are 
encrypted.  Authentication works fine too.  However, I can't seem to 
figure out how to configure OE to use SSL.  No matter what I do tcpdump 
does not show a EHLO message from the client.  Just a bunch of 
gibberish and send mail returns Unknow command to everything.  I saw a 
number of issues listed with OE 4 and STARTTLS on the sendmail web 
pages.  Is that still the problem with 5.0?  Is is usable with any 
available version?