From owner-freebsd-questions@FreeBSD.ORG Fri Nov 1 13:54:27 2013 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.freebsd.org [IPv6:2001:1900:2254:206a::19:1]) (using TLSv1 with cipher ADH-AES256-SHA (256/256 bits)) (No client certificate requested) by hub.freebsd.org (Postfix) with ESMTP id 3211DBAF for ; Fri, 1 Nov 2013 13:54:27 +0000 (UTC) (envelope-from nanog@rsle.net) Received: from mx1.rsle.net (mx1.rsle.net [IPv6:2607:ff40:b0b::4]) (using TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits)) (No client certificate requested) by mx1.freebsd.org (Postfix) with ESMTPS id DB1292E15 for ; Fri, 1 Nov 2013 13:54:26 +0000 (UTC) Received: from prometheus.rsle.net (UNKNOWN [206.162.203.14] (may be forged)) (authenticated bits=0) by mx1.rsle.net (8.14.7/8.14.7) with ESMTP id rA1DsLrJ027907 (version=TLSv1/SSLv3 cipher=DHE-RSA-CAMELLIA256-SHA bits=256 verify=NO) for ; Fri, 1 Nov 2013 09:54:22 -0400 (EDT) (envelope-from nanog@rsle.net) X-Virus-Status: Clean X-Virus-Scanned: clamav-milter 0.98 at antivirus.rsle.net Message-ID: <5273B287.8080000@rsle.net> Date: Fri, 01 Nov 2013 09:54:15 -0400 From: "R. Scott Evans" User-Agent: Mozilla/5.0 (X11; FreeBSD amd64; rv:24.0) Gecko/20100101 Thunderbird/24.0.1 MIME-Version: 1.0 To: freebsd-questions@freebsd.org Subject: Re: [Half OT] Mavericks' Mail and SSL References: <52718078.8080702@netfence.it> In-Reply-To: <52718078.8080702@netfence.it> Content-Type: text/plain; charset=ISO-8859-1; format=flowed Content-Transfer-Encoding: 7bit X-Greylist: Sender succeeded SMTP AUTH, not delayed by milter-greylist-4.4.3 (mx1.rsle.net [206.162.201.2]); Fri, 01 Nov 2013 09:54:22 -0400 (EDT) X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.14 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Fri, 01 Nov 2013 13:54:27 -0000 On 10/30/13 17:56, Andrea Venturoli wrote: > Hello. > > Has anyone tried connecting OS X 10.9's Mail.app to sendmail with SSL? > > Server side all I get is: > >> sm-mta[53510]: STARTTLS=server, error: accept failed=0, reason=unknown, > > SSL_error=5, errno=0, retry=-1, relay=... > > Client side, the SMTP server is marked as offline, with no other > explanation. > Of course it all worked flawlessly until the customer decided to upgrade > from 10.8... > > I couldn't come a to a conlusion myself, but I'm seeing a lot of threads > about this out on the net; however, no solution is proposed. > > My guess is either a bug on the client side (as someone goes on to > suggest) or some exotic variation of the protocol... perhaps I need some > OpenSSL tweak? Some specific settings in sendmail's config? > > I tried both base's and ports' OpenSSL, but nothing seems to change. > > Any hint is appreciated. > > bye & Thanks > av. > _______________________________________________ > freebsd-questions@freebsd.org mailing list > http://lists.freebsd.org/mailman/listinfo/freebsd-questions > To unsubscribe, send any mail to > "freebsd-questions-unsubscribe@freebsd.org" I didn't think to test this until I saw this email but yeah after updating to 10.9 it no longer worked for me either. My almost identical error was: Oct 31 16:20:02 mailer sm-mta[88798]: STARTTLS=server, error: accept failed=-1, reason=unknown protocol, SSL_error=1, errno=0, retry=-1, relay=... and I fixed it in my Mac 10.9 Mail by going to "Mail > Preferences..." and under "Accounts" then "Account Information" and selecting "Edit SMTP Server List.." and finally under "Advanced", I changed from "Use default ports (25, 465, 587)" to "Use custom port" with the value of "587". I didn't change anything on the FreeBSD/Sendmail/SSL server side. Oct 31 16:26:39 mailer sm-mta[95592]: STARTTLS=server, relay=xxxxxxxx [xxx.xxx.xxx.xxx], version=TLSv1/SSLv3, verify=NO, cipher=AES128-SHA, bits=128/128 Oct 31 16:26:39 mailer sm-mta[95592]: AUTH=server, relay=xxxxxxxx [xxx.xxx.xxx.xxx], authid=XXXXX, mech=PLAIN, bits=0 Oct 31 16:26:40 mailer sm-mta[95592]: r9VKQcLs095592: from=, size=349, class=0, nrcpts=1, msgid=<453C3868-D943-4861-8486-DFF788C7F3BE@YYYYYYY.com>, proto=ESMTP, daemon=MSA, relay=... Hope that helps, -scott