From owner-freebsd-questions@freebsd.org Fri Apr 14 19:54:29 2017 Return-Path: Delivered-To: freebsd-questions@mailman.ysv.freebsd.org Received: from mx1.freebsd.org (mx1.freebsd.org [IPv6:2001:1900:2254:206a::19:1]) by mailman.ysv.freebsd.org (Postfix) with ESMTP id F222AD3E769 for ; Fri, 14 Apr 2017 19:54:28 +0000 (UTC) (envelope-from jon@radel.com) Received: from radel.com (fly.radel.com [70.184.242.170]) (using TLSv1 with cipher ECDHE-RSA-AES256-SHA (256/256 bits)) (Client CN "*.radel.com", Issuer "COMODO RSA Domain Validation Secure Server CA" (not verified)) by mx1.freebsd.org (Postfix) with ESMTPS id 40945AF6 for ; Fri, 14 Apr 2017 19:54:26 +0000 (UTC) (envelope-from jon@radel.com) X-CGP-ClamAV-Result: CLEAN X-VirusScanner: Niversoft's CGPClamav Helper v1.19.2 (ClamAV engine v0.99.2) X-ExtFilter: Niversoft's DomainKeys Helper DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws; d=radel.com; s=20170108.radel; h=Subject:To:References:From:Message-ID:Date:User-Agent: MIME-Version:In-Reply-To:Content-Type; b=vNNYmF6BGfYpW3YD1OaalALHXlGrYZy/6QfZYwtL1+y/KmaOmjm5t2kKBALzSG+t4Z kT0AkW6TZf5M9cVcgGLV5Ds7dXATcC+ch1EmJnsM/LqJfSKdg1/6LxHBZko5NwIlYtDQ olPEJJGHehWYswAd8OF9l5T3+cRu1o/OOgTauGjB+uWryv9LkoE/AxoEYjaIn/E7hjmg XOLSL6ABJ54u/lQrSJmIL5dpCqxMd+Lazs4o/tA1iZ2aPPTBhqVNVf8kZCiGc8+j/Voq veIEQbjPokni2jpQH09O3yTjNydCvk4+LqZHBAtrsKOD/oKiYsuHtBpfHX5UJihhBmXC Z8FA== DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=radel.com; s=20170108.radel; t=1492196006; x=1492800806; q=dns/txt; h=Subject:To:References:From:Message-ID:Date: User-Agent:MIME-Version:In-Reply-To:Content-Type; bh=iKza3HbPoDA pDdANM8FuqZW2Pbzwc+Adp8ZZ/ux4NZg=; b=NWXJOAMjSqfccMvGEVLkvSWbeiA QjEkm6lUNrubPp156RWlbwVW4nvSKukjXKKES7HActWwbtn96VjnGXNGyNaLBXdP UXS/vwfFHBx+w6cBTglRtxX3XCdpt6zN9mwUrH/EkzjYu2S0XcgFYjmL1GzoL7at UnPRO/j1YFCMud7eDjOUmX4g5lvk2m8IFJsLRouevvtZy6X99usNRS6Msav8Ke3G yeO3/BYuQOdCw7aJm1pEiWVCJcyB9x9jMY4GWUxQ0GcVG07a8yqsEi7YbL6O1hQW fUn6Vja1Q/YJ9GRjfe6DL7aK4vcelAQJmqnmj3qmhtUGaOb9X+fg51+ge3g== Received: from [2001:470:880a:4389:7095:3d8c:2351:7da5] (account jon@radel.com HELO gravenstein.local) by radel.com (CommuniGate Pro SMTP 6.1.14 _community_) with ESMTPSA id 1308952; Fri, 14 Apr 2017 18:53:26 +0000 Subject: Re: why does some outgoing mail constantly end up "Deferred" ? To: William Dudley , freebsd-questions References: From: Jon Radel Message-ID: <06778058-d9e5-be91-f0f8-78fa37dc6a5a@radel.com> Date: Fri, 14 Apr 2017 14:53:25 -0400 User-Agent: Mozilla/5.0 (Macintosh; Intel Mac OS X 10.10; rv:45.0) Gecko/20100101 Thunderbird/45.8.0 MIME-Version: 1.0 In-Reply-To: Content-Type: multipart/signed; protocol="application/pkcs7-signature"; micalg=sha-256; boundary="------------ms060906000602070208080000" X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.23 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Fri, 14 Apr 2017 19:54:29 -0000 This is a cryptographically signed message in MIME format. --------------ms060906000602070208080000 Content-Type: text/plain; charset=windows-1252 Content-Transfer-Encoding: quoted-printable On 4/14/17 1:37 PM, William Dudley wrote: > This, in /var/log/maillog: >=20 > Apr 14 13:17:52 dudley sm-mta[13944]: v3ALsCcO098060: to=3D< > lemontree66@sbcglobal.net>, delay=3D3+19:23:38, xdelay=3D00:00:00, > mailer=3Desmtp, pri=3D16918651, relay=3Dal-ip4-mx-vip1.prodigy.net., ds= n=3D4.0.0, > stat=3DDeferred > Apr 14 13:17:52 dudley sm-mta[13944]: v3ALsCci098060: to=3D< > markj@limerockcontractors.com>, delay=3D3+19:23:34, xdelay=3D00:00:00, > mailer=3Desmtp, pri=3D16918660, relay=3Dlimerockcontractor...ction.outl= ook.com., > dsn=3D4.0.0, stat=3DDeferred > These mails sit in my queue, get retried, and are constantly "Deferred"= =2E If they were in the queue for only a short period and then were eventually sent, I'd suspect gr[a|e]ylisting. If it were some obscure little domain where the MX host had connectivity problems, well, that would be it. But 3+ days delay, where most of the mail is going to some Microsoft service offering.... It's probably something else. Unless you and/or your ISP have broken TCP port 25 connectivity entirely....but you say that this happens only with some mail. The very first thing I'd do, as root, is to run sendmail -qf -v which will ask sendmail to run through the queues once, in the foreground, and report in verbose mode what it thinks is happening as it tries to send each piece of mail waiting in the queues, and probably most usefully, what text the other side SMTP server sends to explain what it is doing. Assuming that it doesn't just time out trying to reach the remote server, which would also be obvious. Most sensible servers send at least some hints for the humans along with the response code. After that I'd confirm that forward DNS, reverse DNS, and how your SMTP server identifies itself (should be obvious in the verbose output), match up sensibly, and your DNS data is accessible to the Internet at large. Getting that wrong makes you look way too much like some random drive-by spammer. --=20 --Jon Radel jon@radel.com --------------ms060906000602070208080000 Content-Type: application/pkcs7-signature; name="smime.p7s" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="smime.p7s" Content-Description: S/MIME Cryptographic Signature MIAGCSqGSIb3DQEHAqCAMIACAQExDzANBglghkgBZQMEAgEFADCABgkqhkiG9w0BBwEAAKCC Cq8wggSvMIIDl6ADAgECAhEA4CPLFRKDU4mtYW56VGdrITANBgkqhkiG9w0BAQsFADBvMQsw CQYDVQQGEwJTRTEUMBIGA1UEChMLQWRkVHJ1c3QgQUIxJjAkBgNVBAsTHUFkZFRydXN0IEV4 dGVybmFsIFRUUCBOZXR3b3JrMSIwIAYDVQQDExlBZGRUcnVzdCBFeHRlcm5hbCBDQSBSb290 MB4XDTE0MTIyMjAwMDAwMFoXDTIwMDUzMDEwNDgzOFowgZsxCzAJBgNVBAYTAkdCMRswGQYD VQQIExJHcmVhdGVyIE1hbmNoZXN0ZXIxEDAOBgNVBAcTB1NhbGZvcmQxGjAYBgNVBAoTEUNP TU9ETyBDQSBMaW1pdGVkMUEwPwYDVQQDEzhDT01PRE8gU0hBLTI1NiBDbGllbnQgQXV0aGVu dGljYXRpb24gYW5kIFNlY3VyZSBFbWFpbCBDQTCCASIwDQYJKoZIhvcNAQEBBQADggEPADCC 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