From owner-freebsd-questions@FreeBSD.ORG Fri Oct 29 15:36:14 2010 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.freebsd.org [IPv6:2001:4f8:fff6::34]) by hub.freebsd.org (Postfix) with ESMTP id 2ADE71065675 for ; Fri, 29 Oct 2010 15:36:14 +0000 (UTC) (envelope-from vince@unsane.co.uk) Received: from unsane.co.uk (unsane-pt.tunnel.tserv5.lon1.ipv6.he.net [IPv6:2001:470:1f08:110::2]) by mx1.freebsd.org (Postfix) with ESMTP id 7EF378FC0C for ; Fri, 29 Oct 2010 15:36:13 +0000 (UTC) Received: from vhoffman-macbooklocal.local (lon.namesco.net [195.7.254.102]) (authenticated bits=0) by unsane.co.uk (8.14.4/8.14.4) with ESMTP id o9TFaBYN001058 (version=TLSv1/SSLv3 cipher=DHE-RSA-CAMELLIA256-SHA bits=256 verify=NO); Fri, 29 Oct 2010 16:36:11 +0100 (BST) (envelope-from vince@unsane.co.uk) Message-ID: <4CCAE9EA.9000508@unsane.co.uk> Date: Fri, 29 Oct 2010 16:36:10 +0100 From: Vincent Hoffman User-Agent: Mozilla/5.0 (Macintosh; U; Intel Mac OS X 10.6; en-US; rv:1.9.2.11) Gecko/20101013 Thunderbird/3.1.5 MIME-Version: 1.0 To: Christopher Illies References: <4CC98291.8000609@bah.homeip.net> <4CC9E9A9.2090105@unsane.co.uk> , <4CCABB82.9080504@unsane.co.uk> In-Reply-To: X-Enigmail-Version: 1.1.1 Content-Type: text/plain; charset=ISO-8859-1 Content-Transfer-Encoding: 7bit Cc: "freebsd-questions@freebsd.org" Subject: Re: Sendmail as client via smarthost and ssl X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.5 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Fri, 29 Oct 2010 15:36:14 -0000 On 29/10/2010 14:49, Christopher Illies wrote: > Thanks for your explanations, Vince. It got me one step further (I think). > > <...> > Ok, when I use telnet, this happens: >> telnet send.ki.se 587 > Trying 130.xxx.xxx.26... > Connected to send.ki.se. > Escape character is '^]'. > 220 KIMSX09.user.ki.se Microsoft ESMTP MAIL Service ready at Fri, 29 Oct 2010 14:55:51 +0200 > EHLO > 250-KIMSX09.user.ki.se Hello [136.xxx.xxx.214] > 250-SIZE 10485760 > 250-PIPELINING > 250-DSN > 250-ENHANCEDSTATUSCODES > 250-STARTTLS > 250-AUTH GSSAPI NTLM <<<<<<< > 250-8BITMIME > 250-BINARYMIME > 250 CHUNKING > > > Although I have no idea what GSSAPI and NTLM are, I remembered that I have > seen these abbreviations before: NTLM is an OPTION for cyrus-sasl2, and yes, > it is compiled in (WITH_NTLM=true). And GSSAPI appeared first in the mc file: > > define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl > > So I changed the authinfo/client-info file to: > > AuthInfo:[send.ki.se] "U:smmsp" "I:XXX" "P:YYY" "M:GSSAPI" > > Still, it does not work: > > <<< 530 5.7.1 Client was not authenticated I'd guess from here that the microsoft mail server (i'd say exchange but its part of IIS these days i think) is being awkward. GSSAPI is kerberos related i believe, NTLM is a windows method from what i remember. I'm not familiar with either i'm afraid. Vince > Christopher >