From owner-freebsd-questions@FreeBSD.ORG Sat Mar 30 17:23:44 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 E551DC3D for ; Sat, 30 Mar 2013 17:23:44 +0000 (UTC) (envelope-from mexas@bristol.ac.uk) Received: from eu1sys200aog102.obsmtp.com (eu1sys200aog102.obsmtp.com [207.126.144.113]) by mx1.freebsd.org (Postfix) with ESMTP id 42CE61DF for ; Sat, 30 Mar 2013 17:23:43 +0000 (UTC) Received: from mail-we0-f199.google.com ([74.125.82.199]) (using TLSv1) by eu1sys200aob102.postini.com ([207.126.147.11]) with SMTP ID DSNKUVcfmS3US1AoaTNnKfETcD57RCHAepXT@postini.com; Sat, 30 Mar 2013 17:23:44 UTC Received: by mail-we0-f199.google.com with SMTP id t11so1865497wey.2 for ; Sat, 30 Mar 2013 10:23:37 -0700 (PDT) X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=20120113; h=x-received:x-received:date:from:message-id:to:subject:reply-to :in-reply-to:x-gm-message-state; bh=Av57/meFTJa2L7vn0o6L8OwjFtmoHrIVUswDXVYq1AE=; b=BMugk10XawPdu0Lo+AyUNxaJx17gSOXE/cMheWpnw4vMXieaq+ofx20TX9+w6UtiAR xR+QswvP1XDyLxo3RVe35kBU3ZanR2ca3336IQtZcqnoyHivMvE0BxAqPqLv3QXiHpTd ZyJFadEpA0a++Qpch03nilaov/tqRVkTJzH+FBx8vUN062jvB54fQsAbMY/OnxEvx1rD hGqVyJOtyttDt5KkbsZOpJs5r7YgV8NSfm+bVnDz1l6wz/dU3swAoVkX5QPK64LSPhwl kAEg8DgHNm5ondch2qV3VMqCSE239qHzRZLTSoGE9+MrE4NWH2aN4PVNapEA9e3f8sx6 jJ3A== X-Received: by 10.194.11.70 with SMTP id o6mr3884242wjb.29.1364663877073; Sat, 30 Mar 2013 10:17:57 -0700 (PDT) X-Received: by 10.194.11.70 with SMTP id o6mr3884235wjb.29.1364663876946; Sat, 30 Mar 2013 10:17:56 -0700 (PDT) Received: from mech-cluster241.men.bris.ac.uk (mech-cluster241.men.bris.ac.uk. [137.222.187.241]) by mx.google.com with ESMTPS id fv2sm4806389wib.6.2013.03.30.10.17.54 (version=TLSv1.2 cipher=ECDHE-RSA-RC4-SHA bits=128/128); Sat, 30 Mar 2013 10:17:55 -0700 (PDT) Received: from mech-cluster241.men.bris.ac.uk (localhost [127.0.0.1]) by mech-cluster241.men.bris.ac.uk (8.14.6/8.14.6) with ESMTP id r2UHHrka083178 (version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-GCM-SHA384 bits=256 verify=NO) for ; Sat, 30 Mar 2013 17:17:53 GMT (envelope-from mexas@mech-cluster241.men.bris.ac.uk) Received: (from mexas@localhost) by mech-cluster241.men.bris.ac.uk (8.14.6/8.14.6/Submit) id r2UHHrd2083177 for freebsd-questions@freebsd.org; Sat, 30 Mar 2013 17:17:53 GMT (envelope-from mexas) Date: Sat, 30 Mar 2013 10:17:55 -0700 (PDT) From: Anton Shterenlikht Message-Id: <201303301717.r2UHHrd2083177@mech-cluster241.men.bris.ac.uk> To: freebsd-questions@freebsd.org Subject: Re: Operation timed out with smtp.gmail.com - please help In-Reply-To: <20130330074919.7902b8c2@scorpio> X-Gm-Message-State: ALoCoQkIaXcy3tZGKkakNbRFOkPC7YEinA6ZCIUfP818eYnkHthg88lV+9J382/h2lhBfG6afWN59MOzjSzN/ro+yPCpqweI7jPPymiO2lhmIpVBg8Jvx8y7QjrFCtuXJbAxMFA5Md3Thg3fs2LXwun521n+H9dTuXgjua/BByUEkZispGavwqU= X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.14 Precedence: list Reply-To: mexas@bristol.ac.uk List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Sat, 30 Mar 2013 17:23:45 -0000 Date: Sat, 30 Mar 2013 07:49:19 -0400 From: Jerry To: FreeBSD Subject: Re: Operation timed out with smtp.gmail.com - please help On Sat, 30 Mar 2013 10:49:45 +0000 Matthew Seaman articulated: > Given you're seeing that CONNECTED message there, it certainly does. > The problem with that openssl command seems to be the 'unable to get > local issuer certificate' part. That's possibly openssl being pickier > about verifying certs than sendmail would be, but that certificate > verification step is probably where you're coming adrift. You need to > have the intermediate certs used by Google in your cacert.pem file, so > sendmail will trust the smtp.gmail.com cert. Check the 'confCACERT' > setting in your sendmail.mc. I have a block of code like this: >=20 > define(`CERT_DIR', `MAIL_SETTINGS_DIR`'certs')dnl > define(`confCACERT_PATH', `CERT_DIR')dnl > define(`confCACERT', `CERT_DIR/cacert.pem')dnl > define(`confSERVER_CERT', `CERT_DIR/cert.pem')dnl > define(`confSERVER_KEY', `CERT_DIR/key.pem')dnl > define(`confCLIENT_CERT', `CERT_DIR/cert.pem')dnl > define(`confCLIENT_KEY', `CERT_DIR/key.pem')dnl >=20 > which allows me to put all the keys and certs in /etc/mail/certs/ If you really need the Gmail certs, you can use this to get them: openssl s_client -connect smtp.gmail.com:587 -starttls smtp -showcerts If you feel you really need the "Equifax Secure Certificate Authority" pem, go here and download it. Again, how to set up Sendmail is a task I leave for the student. Jerry, Matthew, thank you I think I got it working. In addition to your advice, this guide was very helpful: http://www.phinesolutions.com/sendmail-gmail-smtp-relay-howto.html It seems these two options were required: define(`RELAY_MAILER_ARGS', `TCP $h 587') define(`ESMTP_MAILER_ARGS', `TCP $h 587') Thanks again Anton