From owner-freebsd-questions@FreeBSD.ORG Fri Nov 1 19:12:45 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 30270E23 for ; Fri, 1 Nov 2013 19:12:45 +0000 (UTC) (envelope-from freebsd-questions@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 D7E1F21FE for ; Fri, 1 Nov 2013 19:12:44 +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 rA1JCeRB037147 (version=TLSv1/SSLv3 cipher=DHE-RSA-CAMELLIA256-SHA bits=256 verify=NO); Fri, 1 Nov 2013 15:12:40 -0400 (EDT) (envelope-from freebsd-questions@rsle.net) X-Virus-Status: Clean X-Virus-Scanned: clamav-milter 0.98 at antivirus.rsle.net Message-ID: <5273FD23.7090207@rsle.net> Date: Fri, 01 Nov 2013 15:12:35 -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: Andrea Venturoli Subject: Re: [Half OT] Mavericks' Mail and SSL References: <52718078.8080702@netfence.it> <5272C747.8030805@rsle.net> <5273EF3F.8040307@netfence.it> In-Reply-To: <5273EF3F.8040307@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 15:12:40 -0400 (EDT) Cc: freebsd-questions@freebsd.org 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 19:12:45 -0000 On 11/01/13 14:13, Andrea Venturoli wrote: > On 10/31/13 22:10, R. Scott Evans wrote: > > Hi Scott. > > First of all, thanks for your reply. > > >> 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. > > I'm using port 465 and I tried manually setting it, but it did not help. > > Using 587, you mean you are using TLS, not SSL, right? > > bye & Thanks > av. I offer both SSL/TLS (465) and STARTTLS (587) to my users. In the Mac Mail I don't see an option for differentiating the connection security between SSL/TLS and STARTTLS other than specifying the port manually. There is a checkbox to Use SSL regardless of what port option is used (which I obviously have checked). Anyhow, I changed the port on my Mac to 465 and it still worked for me. Then again, I also just tried switching it back to the "default (25, 465, 587)" option for the port and it now works with that also, so I'm not sure what is going on? -scott