From owner-freebsd-questions@FreeBSD.ORG Sat Nov 6 16:50:26 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 1791F106564A for ; Sat, 6 Nov 2010 16:50:26 +0000 (UTC) (envelope-from FreeBSD@insightbb.com) Received: from mxsf12.insightbb.com (mxsf12.insightbb.com [74.128.0.94]) by mx1.freebsd.org (Postfix) with ESMTP id D62C98FC08 for ; Sat, 6 Nov 2010 16:50:25 +0000 (UTC) X-IronPort-AV: E=Sophos;i="4.58,308,1286164800"; d="scan'208";a="199380953" Received: from unknown (HELO asav01.insightbb.com) ([172.31.249.123]) by mxsf12.insightbb.com with ESMTP; 06 Nov 2010 12:50:25 -0400 X-IronPort-Anti-Spam-Filtered: true X-IronPort-Anti-Spam-Result: Aqc3AJ8j1UxKgCiCO2dsb2JhbACIA4wIjX0MAQEBATUtvQeDBAgBBAWCMgQ X-IronPort-AV: E=Sophos;i="4.58,308,1286164800"; d="scan'208";a="304822615" Received: from 74-128-40-130.dhcp.insightbb.com (HELO laptop2.stevenfriedrich.org) ([74.128.40.130]) by asavout01.insightbb.com with ESMTP; 06 Nov 2010 12:50:24 -0400 From: Steven Friedrich To: freebsd-questions@freebsd.org Date: Sat, 6 Nov 2010 12:50:23 -0400 User-Agent: KMail/1.13.5 (FreeBSD/8.1-RELEASE-p1; KDE/4.5.3; i386; ; ) References: <201011060723.39786.FreeBSD@insightbb.com> <20101106160153.GA12418@guilt.hydra> In-Reply-To: <20101106160153.GA12418@guilt.hydra> MIME-Version: 1.0 Content-Type: Text/Plain; charset="iso-8859-15" Content-Transfer-Encoding: 7bit Message-Id: <201011061250.24353.FreeBSD@insightbb.com> Subject: Re: ssmtp - possible anomaly with 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: Sat, 06 Nov 2010 16:50:26 -0000 On Saturday 06 November 2010 12:01:53 pm Chad Perrin wrote: > On Sat, Nov 06, 2010 at 07:23:39AM -0400, Steven Friedrich wrote: > > I recently figured out how to send mail thru my ISP ID using ssmtp. I > > had previously only been using KMail, and I had it configured to use > > port 465 SSL LOGIN. > > > > I can send mail when I don't use port 465: > > mailhub=mail.InsightBB.com > > > > but if I add the port 465 a,d enable SSL with: > > UseTLS=YES > > > > then I use the -v switch and also -auFreeBSD -apPassword > > as in smtp -v -auFreeBSD -apPassword freebsd@insightbb.com > > > > and the messages all indicate success, but the mail never arrives. It > > does when I don't use SSL on port 465. > > > > KMail does work with SSL on port 465. > > I'm not entirely clear on what you're using as a mail user agent. Are > you still using KMail as your MUA, but using ssmtp to send the emails to > your SMTP server, or have you switched MUAs when you started using ssmtp? > > Chris Brennan suggested you send more information; in addition to > answering my question, it might be useful to give us the information > Chris requested -- but make sure you obscure any username/password > information. I still use KMail for my essential email. However, I want to be able to use send-pr. There is a port called ssmtp, and I use it only for outgoing mail, it allows any userID to send outgoing email using a single ISP account. When my /usr/local/etc/ssmtp.conf is: root=FreeBSD@InsightBB.com mailhub=mail.InsightBB.com rewriteDomain=InsightBB.com hostname=_HOSTNAME_ I can send an outgoing email to myself so I can prove it works. ssmtp -v freebsd@insighttbb.com And the verbose output indicates success. I didn't post it, just stated what it was. But when I configure SSL on port 465, it also shows a good exchange, but maybe I didn't wait long enough to see it get thru the ISP's system. So my SSL version of ssmtp.conf is: root=FreeBSD@InsightBB.com mailhub=mail.InsightBB.com:465 rewriteDomain=InsightBB.com hostname=_HOSTNAME_ # Use SSL/TLS to send secure messages to server. UseTLS=YES The verbose option indicated success when sending an email from root. Let me verify that it wasn't my mistake for not waiting longer... -- System Name: laptop2.StevenFriedrich.org Hardware: 2.80GHz Intel Pentium 4 (HTT) with 2 GB memory OS version: FreeBSD 8.1-RELEASE-p1 i386 (6.4 MB kernel) manager(s): kde4-4.5.3 X windows: xorg-7.5 X.Org X Server 1.7.5