From owner-freebsd-questions@FreeBSD.ORG Sat Nov 6 20:21:20 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 32C18106564A for ; Sat, 6 Nov 2010 20:21:20 +0000 (UTC) (envelope-from perrin@apotheon.com) Received: from cpoproxy2-pub.bluehost.com (cpoproxy2-pub.bluehost.com [67.222.39.38]) by mx1.freebsd.org (Postfix) with SMTP id ED93E8FC16 for ; Sat, 6 Nov 2010 20:21:19 +0000 (UTC) Received: (qmail 26937 invoked by uid 0); 6 Nov 2010 20:21:19 -0000 Received: from unknown (HELO box543.bluehost.com) (74.220.219.143) by cpoproxy2.bluehost.com with SMTP; 6 Nov 2010 20:21:19 -0000 DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws; s=default; d=apotheon.com; h=Date:From:To:Subject:Message-ID:Mail-Followup-To:References:Mime-Version:Content-Type:Content-Disposition:In-Reply-To:User-Agent:X-Identified-User; b=MAlPp45eyD29cq2nri7CHh0P+voDZN0yq892EDWtwCEH9TvPSlZJY24dAavzj5BTMYDdAeVWKl6DDmnizZi6ptKEVa/VTFL6s5GTcs77F70EYQX9cwbJvWA4icyiYSvP; Received: from c-24-8-180-234.hsd1.co.comcast.net ([24.8.180.234] helo=kukaburra.hydra) by box543.bluehost.com with esmtpsa (TLSv1:AES256-SHA:256) (Exim 4.69) (envelope-from ) id 1PEpGH-00013a-U2 for freebsd-questions@freebsd.org; Sat, 06 Nov 2010 14:21:19 -0600 Received: by kukaburra.hydra (sSMTP sendmail emulation); Sat, 06 Nov 2010 14:15:22 -0600 Date: Sat, 6 Nov 2010 14:15:22 -0600 From: Chad Perrin To: freebsd-questions@freebsd.org Message-ID: <20101106201522.GA13095@guilt.hydra> Mail-Followup-To: freebsd-questions@freebsd.org References: <201011060723.39786.FreeBSD@insightbb.com> <20101106160153.GA12418@guilt.hydra> <201011061250.24353.FreeBSD@insightbb.com> Mime-Version: 1.0 Content-Type: multipart/signed; micalg=pgp-sha1; protocol="application/pgp-signature"; boundary="HlL+5n6rz5pIUxbD" Content-Disposition: inline In-Reply-To: User-Agent: Mutt/1.4.2.3i X-Identified-User: {2737:box543.bluehost.com:apotheon:apotheon.org} {sentby:smtp auth 24.8.180.234 authed with ren@apotheon.org} 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 20:21:20 -0000 --HlL+5n6rz5pIUxbD Content-Type: text/plain; charset=us-ascii Content-Disposition: inline Content-Transfer-Encoding: quoted-printable On Sat, Nov 06, 2010 at 12:54:39PM -0400, Chris Brennan wrote: > On Sat, Nov 6, 2010 at 12:50 PM, Steven Friedrich = wrote: > > > > I still use KMail for my essential email. Okay, thanks for clarifying, Steven. > > > > 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=3DFreeBSD@InsightBB.com > > mailhub=3Dmail.InsightBB.com:465 > > rewriteDomain=3DInsightBB.com > > hostname=3D_HOSTNAME_ > > # Use SSL/TLS to send secure messages to server. > > UseTLS=3DYES > > > > The verbose option indicated success when sending an email from > > root. Let me verify that it wasn't my mistake for not waiting > > longer... =2E . . and you said that setting it to send email through mail.insightbb.com:465 in KMail config works. Right? In addition to Chris Brennan's article references, there's another that I wrote quite some time ago that I think explains ssmtp config for TLS use pretty well: http://blogs.techrepublic.com.com/security/?p=3D440 =46rom what you said so far, it seems like ssmtp is configured correctly. It seems likely, then, that the problem is with KMail or with something filtering port 465. Does KDE have something going on with firewall management that might be allowing KMail to send stuff on port 465 while outside of KDE's "help" you cannot? Have you checked to see whether you can send with your TLS settings for ssmtp from outside of KMail? If you are not wedded to ssmtp per se, you could always try msmtp instead: http://blogs.techrepublic.com.com/opensource/?p=3D1842 It does much the same sort of stuff as ssmtp, but is a bit more "feature rich", and appears to be more actively maintained than ssmtp. >=20 > /var/log/maillog is where you will see success/fail. Your config looks go= od > to me, so I would watch maillog while sending mail and see what crops up. It appears that Chris Brennan knows a bit about this subject. Yes, that file may prove useful in troubleshooting this issue. If you are having trouble figuring out whether maillog has anything to offer for hints, you might want to paste its contents into pastebin and give us a link to it there so we can give it a look (after checking to make sure you are not pasting any sensitive data, of course). --=20 Chad Perrin [ original content licensed OWL: http://owl.apotheon.org ] --HlL+5n6rz5pIUxbD Content-Type: application/pgp-signature Content-Disposition: inline -----BEGIN PGP SIGNATURE----- Version: GnuPG v2.0.14 (FreeBSD) iEYEARECAAYFAkzVt1oACgkQ9mn/Pj01uKXuSQCgjsxTcm2DEnuOQydpZH/aHsDV W0cAoPAbTPAOReIKjjhXjUayOZstlNZC =93zG -----END PGP SIGNATURE----- --HlL+5n6rz5pIUxbD--