On Wed, 26 May 2004, Lee Dilkie wrote:

You've got "This server requires a secure connection (SSL)"
enabled for
the SMTP server in Outlook?

In my experience (outlook 2000, not tested on outlook express) this won't work. Outlook doesn't seem to understand that "use SSL" means "use STARTLS". What I did was to configure sendmail to also support "smtps" (SSL before SMTP) on the smtps port (465) and point outlook at that port with the "use ssl" checked.

Outlook 2002 (from Office XP) will try STARTTLS if SMTP-over-SSL doesn't work for any port other than 25, apparently, but as I said, it's still a bit hairy. I've got clients in .us, .uk, and .nz doing this with my server in .nz. FWIW, I believe Microsoft are still working on this - I'm told they might default to trying STARTTLS first for port 587. These things take time; the MSA standard is only about five years old, after all...



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