From owner-freebsd-questions@freebsd.org Fri Apr 14 21:38:25 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 0628AD3C0F6 for ; Fri, 14 Apr 2017 21:38:25 +0000 (UTC) (envelope-from wfdudley@gmail.com) Received: from mail-yb0-x236.google.com (mail-yb0-x236.google.com [IPv6:2607:f8b0:4002:c09::236]) (using TLSv1.2 with cipher ECDHE-RSA-AES128-GCM-SHA256 (128/128 bits)) (Client CN "smtp.gmail.com", Issuer "Google Internet Authority G2" (verified OK)) by mx1.freebsd.org (Postfix) with ESMTPS id B8A2CAFB for ; Fri, 14 Apr 2017 21:38:24 +0000 (UTC) (envelope-from wfdudley@gmail.com) Received: by mail-yb0-x236.google.com with SMTP id i124so21191008ybc.3 for ; Fri, 14 Apr 2017 14:38:24 -0700 (PDT) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=gmail.com; s=20161025; h=mime-version:in-reply-to:references:from:date:message-id:subject:to :cc; bh=4ELCdlxA8Bi0/YU3QTlFD6Kyj71lI9FwjT88w5yzYmQ=; b=GciyTCith9BqTBJmjGPeIII98PoPknV+FHBY/JZiWHtAT1PMWrUBiQv28osFXZ2Xgu 8P1Ruh8y9a7sPJu/Ny5nuFBNqWpSsqiUtk8FOFmRLLMjUzRCSuOAZrMuLzKfMHXIAl9/ 8yHzufd5/LcUjqmHwMxCJXbeiC/8ZPsaHA6/rpl4kPaozygRL1FFlDZGptjtum00d7w+ yLCi9H1pMloAYTaa70JZi4IjPwV3cz6m2Vlqdv/mi5ssZep58Hfuohi6pXQLW+pK+I+I 8nZdIkPuXZQpoAF9BZUuc/NleLbWeuzg2fgFfrTfBOmg5tQUukFlDp1TBgCfL++EabVU wC6Q== X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=1e100.net; s=20161025; h=x-gm-message-state:mime-version:in-reply-to:references:from:date :message-id:subject:to:cc; bh=4ELCdlxA8Bi0/YU3QTlFD6Kyj71lI9FwjT88w5yzYmQ=; b=YrYAsBwWWDHiOroh/DdXa2wY8V5cUmTirmt5xdf/MUEfn2BVl98dKFGbr/LWkymF7h x9sys2r7zB7utSqDcvyxBJDCk0kOJDROAsuDiLj1TZvKKt/MxMpIxhh7W0qW5BibNDCU 1doj2Q13RSJNYR3twz1d3LB15TctqPb7tOP5yP6weuMlF8/+6f/Cpo0VyCfOC2aMi68t YK/iSP8PlY4Dk8PW6z70LigRmo4fxekZlYXC+OSawbAahtIKjBkoijpaH1p6p2tybz+U pY5yP4+vGgdh/YMtms/Wp270MU/ffjK2Do9kky1zSYHCICnJRzn1NXdTYSxeEiccqk3a HL0Q== X-Gm-Message-State: AN3rC/4G4wgL5arV9gfgfbfnLcpXEyABnnUVV6EO8Ix4TWDPm4ONKP7I JQ8bYApNN2o7VCefBU/yXxPkaw4lbg== X-Received: by 10.37.230.198 with SMTP id d189mr6394499ybh.99.1492205903871; Fri, 14 Apr 2017 14:38:23 -0700 (PDT) MIME-Version: 1.0 Received: by 10.37.163.227 with HTTP; Fri, 14 Apr 2017 14:38:23 -0700 (PDT) In-Reply-To: <06778058-d9e5-be91-f0f8-78fa37dc6a5a@radel.com> References: <06778058-d9e5-be91-f0f8-78fa37dc6a5a@radel.com> From: William Dudley Date: Fri, 14 Apr 2017 17:38:23 -0400 Message-ID: Subject: Re: why does some outgoing mail constantly end up "Deferred" ? To: Jon Radel Cc: freebsd-questions Content-Type: text/plain; charset=UTF-8 X-Content-Filtered-By: Mailman/MimeDel 2.1.23 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 21:38:25 -0000 Thanks, that was very helpful. My problem was a broken STARTTLS implementation -- so the connection would fail when that failed, and the mail got deferred. For now, I've turned off STARTTLS stuff entirely. Bill Dudley This email is free of malware because I run Linux. On Fri, Apr 14, 2017 at 2:53 PM, Jon Radel wrote: > On 4/14/17 1:37 PM, William Dudley wrote: > > This, in /var/log/maillog: > > > > Apr 14 13:17:52 dudley sm-mta[13944]: v3ALsCcO098060: to=< > > lemontree66@sbcglobal.net>, delay=3+19:23:38, xdelay=00:00:00, > > mailer=esmtp, pri=16918651, relay=al-ip4-mx-vip1.prodigy.net., > dsn=4.0.0, > > stat=Deferred > > Apr 14 13:17:52 dudley sm-mta[13944]: v3ALsCci098060: to=< > > markj@limerockcontractors.com>, delay=3+19:23:34, xdelay=00:00:00, > > mailer=esmtp, pri=16918660, relay=limerockcontractor...ction.outlook.com > ., > > dsn=4.0.0, stat=Deferred > > > > > These mails sit in my queue, get retried, and are constantly "Deferred". > > 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. > > > -- > --Jon Radel > jon@radel.com > >