From owner-freebsd-questions@FreeBSD.ORG Fri Oct 29 13:50:44 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 7DB9B1065672 for ; Fri, 29 Oct 2010 13:50:44 +0000 (UTC) (envelope-from Christopher.Illies@ki.se) Received: from smtp5.ki.se (smtp5.ki.se [130.237.99.130]) by mx1.freebsd.org (Postfix) with ESMTP id 090CE8FC15 for ; Fri, 29 Oct 2010 13:50:43 +0000 (UTC) Received: from KIMSX09.user.ki.se (kimsx09.user.ki.se [130.229.20.26]) by smtp5.ki.se (Postfix) with ESMTP id 43C122955DD; Fri, 29 Oct 2010 15:50:42 +0200 (CEST) Received: from KIMSXCLU01.user.ki.se ([fe80::5934:e0d5:1ab1:4cec]) by KIMSX09.user.ki.se ([fe80::44bd:1e0f:a2f2:550%16]) with mapi; Fri, 29 Oct 2010 15:49:47 +0200 From: Christopher Illies To: Vincent Hoffman Date: Fri, 29 Oct 2010 15:49:46 +0200 Thread-Topic: Sendmail as client via smarthost and ssl Thread-Index: Act3Y13Ld6jLD1EiSM+uSJYttc7luQABqj2v Message-ID: References: <4CC98291.8000609@bah.homeip.net> <4CC9E9A9.2090105@unsane.co.uk> , <4CCABB82.9080504@unsane.co.uk> In-Reply-To: <4CCABB82.9080504@unsane.co.uk> Accept-Language: en-US, sv-SE Content-Language: en-US X-MS-Has-Attach: X-MS-TNEF-Correlator: acceptlanguage: en-US, sv-SE Content-Type: text/plain; charset="us-ascii" Content-Transfer-Encoding: quoted-printable MIME-Version: 1.0 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 13:50:44 -0000 Thanks for your explanations, Vince. It got me one step further (I think). <...> >PLAIN mechanism mean that i'm sending the password/user in plain rather >than using something like DIGEST-MD5 or any of the other possible >mechanisms that can be listed in confAUTH_MECHANISMS in your sendmail >.mc file > >to get a list of whats supported by your relay telnet to it on port 25 >and issue an EHLO command. the supported mechanisms are listed following >the AUTH keyword. > >for example for me >(11:59:59 <~>) 1 $ telnet RELAY.ISP.net 25 >Trying 213.xxx.xxx.53... >Connected to RELAY.ISP.net. <...> >250-AUTH LOGIN PLAIN ---THIS ONE. >250-STARTTLS >250-DELIVERBY >250 HELP 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 20= 10 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=3Dtrue). And GSSAPI appeared first in the mc f= ile: define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PL= AIN')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 Christopher