From owner-freebsd-questions@FreeBSD.ORG Fri Mar 29 19:41:33 2013 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.FreeBSD.org [8.8.178.115]) by hub.freebsd.org (Postfix) with ESMTP id EB225601 for ; Fri, 29 Mar 2013 19:41:33 +0000 (UTC) (envelope-from jerry@seibercom.net) Received: from mail-gh0-f180.google.com (mail-gh0-f180.google.com [209.85.160.180]) by mx1.freebsd.org (Postfix) with ESMTP id A0EF67EC for ; Fri, 29 Mar 2013 19:41:33 +0000 (UTC) Received: by mail-gh0-f180.google.com with SMTP id f13so70284ghb.11 for ; Fri, 29 Mar 2013 12:41:27 -0700 (PDT) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=seibercom.net; s=google; h=x-received:date:from:to:subject:message-id:in-reply-to:references :reply-to:organization:x-mailer:face:mime-version:content-type :content-transfer-encoding; bh=hRBKRkEQwllEfIstNfi6+8A9YOzRKPfXz1odX74dj6Y=; b=dcGAntyOfziltDBq6LhYbPnPi+P6Ilu1NpyELWH5tTQdpzizO+a1q0W32eEc1sCWNU I3GHx2HBza/gfr3EaG37XdeBHg7oQO7fw4/l2d/Dr++1I0CBYp9Ych3sDjsD63Xgie44 0VlToEUzwBC9zqZZ//x4f56hlYegAIv1eg8Vw= X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=20120113; h=x-received:date:from:to:subject:message-id:in-reply-to:references :reply-to:organization:x-mailer:face:mime-version:content-type :content-transfer-encoding:x-gm-message-state; bh=hRBKRkEQwllEfIstNfi6+8A9YOzRKPfXz1odX74dj6Y=; b=KV19Cr7cqS4TRml+QjzV1LmdvEo05ZGk7vnaJFOQB6zXD+zb8i0Zz+Pp75YmZCGBYD Xii/nBzb0d9XBmAzwGTGFLS824XM1hx+D4EdU7ir+WPU/8/Bl0kNVvsSA9pIx2yLmoLj /95WOCgujBvO0C0zBFzsiMRmcew1HTvOrWJ4n/ELcpQDIPhXXWt5HhZzmQhgh/HuMuGs o+pXZVIoLQuoaYVOrQupTLj3Vmy0r6jM0ETb2fSaXy2KJbCMN01D/32ImhWtZ8rPkHxM ZyYSCKSrIXr6SCuF9yXvhB6rgFBo1UPOrCpBlr6TuOlZE/Hsf7EA/urPYjQlnQwor447 wR9Q== X-Received: by 10.236.124.37 with SMTP id w25mr1194186yhh.71.1364585781239; Fri, 29 Mar 2013 12:36:21 -0700 (PDT) Received: from scorpio.seibercom.net (cpe-076-182-104-150.nc.res.rr.com. [76.182.104.150]) by mx.google.com with ESMTPS id z12sm2981396yhg.8.2013.03.29.12.36.20 (version=TLSv1.2 cipher=ECDHE-RSA-RC4-SHA bits=128/128); Fri, 29 Mar 2013 12:36:20 -0700 (PDT) Received: from scorpio (localhost [127.0.0.1]) (using TLSv1.2 with cipher DHE-RSA-AES128-SHA (128/128 bits)) (No client certificate requested) (Authenticated sender: jerry@seibercom.net) by scorpio.seibercom.net (Postfix) with ESMTPSA id 3ZctVC3fLwz2CG4t for ; Fri, 29 Mar 2013 15:36:19 -0400 (EDT) Date: Fri, 29 Mar 2013 15:36:19 -0400 From: Jerry To: FreeBSD Subject: Re: Operation timed out with smtp.gmail.com - please help Message-ID: <20130329153619.69c5b4dd@scorpio> In-Reply-To: <201303291832.r2TIWYPW035723@zzz.men.bris.ac.uk> References: <201303291832.r2TIWYPW035723@zzz.men.bris.ac.uk> Organization: seibercom.net X-Mailer: Claws Mail 3.9.0 (GTK+ 2.24.17; amd64-portbld-freebsd8.3) Face: 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 Mime-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit X-Gm-Message-State: ALoCoQlltCNvxvpWUJgyGBW+mJo4xFqDdlQbNNG4nA4Il3e0c9p9NCkFldXwFFklBSJLMTsMznJf X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.14 Precedence: list Reply-To: FreeBSD List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Fri, 29 Mar 2013 19:41:34 -0000 On Fri, 29 Mar 2013 18:32:34 GMT Anton Shterenlikht articulated: > Please help debug sendmail / smtp.gmail config. > > My University just switched to gmail (dickheads) > and I'm trying to figure out how to set it up. > > It used to work ok with the University smtp auth > server. Now I get in /var/log/maillog: > > sm-mta[72300]: r2TI0vQc072134: to=, > ctladdr= (1001/1001), > delay=00:20:01, xdelay=00:00:00, mailer=relay, pri=210424, > relay=smtp.gmail.com, dsn=4.0.0, > stat=Deferred: Operation timed out with smtp.gmail.com > > I switched the firewall off completely. > > I have: > > # cat /etc/mail/auth/client-info > AuthInfo:smtp.gmail.com "U:root" "I:mexas@bristol.ac.uk" "P:xxxxx" > # > > and this in /etc/mail/freebsd.mc: > > define(`confAUTH_MECHANISMS', `GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN')dnl > define(`SMART_HOST', `smtp.gmail.com')dnl > > I rebuilt (run make under /etc/mail. This just > renames freebsd.mc to .mc, and freebsd.submit.mc > to .submit.mc) and restarted sendmail. > > I also use: > > MASQUERADE_AS(`bristol.ac.uk') > MASQUERADE_DOMAIN(`bristol.ac.uk') > > to use the university domain instead of > may xxxx.men.bris.ac.uk, which is not > acceptable. Try this at the command line: openssl s_client -connect smtp.gmail.com:25 -starttls smtp If it times out, change the port number to 587 and try it again. If you cannot make a connect using either port number then you have a firewall problem. -- Jerry ♔ Disclaimer: off-list followups get on-list replies or get ignored. Please do not ignore the Reply-To header. __________________________________________________________________