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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?