Date: Thu, 27 May 2004 10:05:33 +1200 From: Richard Stevenson <richard@endace.com> To: Lee Dilkie <lee@dilkie.com> Cc: freebsd-questions@freebsd.org Subject: RE: SMTP AUTH Message-ID: <Pine.LNX.4.60.0405271002590.26063@zhba.rg.raqnpr.pbz> In-Reply-To: <107301c44313$b67be8f0$c10133ce@dilkie.com> References: <107301c44313$b67be8f0$c10133ce@dilkie.com>
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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... Cheers Richard -- Richard Stevenson
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