From owner-freebsd-questions@FreeBSD.ORG Wed May 26 15:05:07 2004 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.FreeBSD.org (mx1.freebsd.org [216.136.204.125]) by hub.freebsd.org (Postfix) with ESMTP id 5F86916A4CE for ; Wed, 26 May 2004 15:05:07 -0700 (PDT) Received: from et.endace.com (et.endace.com [219.88.101.154]) by mx1.FreeBSD.org (Postfix) with ESMTP id A6CEC43D41 for ; Wed, 26 May 2004 15:05:05 -0700 (PDT) (envelope-from richard@endace.com) Received: from muon.et.endace.com (muon.et.endace.com [192.168.64.11]) by et.endace.com (8.12.11/8.12.11) with ESMTP id i4QM4JMT035135 (version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-SHA bits=256 verify=NOT) for ; Thu, 27 May 2004 10:04:19 +1200 (NZST) Received: from localhost (localhost [127.0.0.1]) (authenticated bits=0)i4QM5hRx026133 (version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-SHA bits=256 verify=NOT); Thu, 27 May 2004 10:05:49 +1200 Date: Thu, 27 May 2004 10:05:33 +1200 From: Richard Stevenson To: Lee Dilkie In-Reply-To: <107301c44313$b67be8f0$c10133ce@dilkie.com> Message-ID: References: <107301c44313$b67be8f0$c10133ce@dilkie.com> Comments: PGP Public Key on keyservers: Key ID FA6D9719 MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII; format=flowed X-Scanned-By: milter-gris/0.1.14 (et.endace.com [192.168.64.254]); Thu, 27 May 2004 10:04:19 +1200 X-Virus-Scanned: clamd / ClamAV version devel-20040408, clamav-milter version 0.70g cc: 'Noah' cc: freebsd-questions@freebsd.org Subject: RE: SMTP AUTH X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.1 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Wed, 26 May 2004 22:05:07 -0000 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