Date: Fri, 14 Apr 2017 17:38:23 -0400 From: William Dudley <wfdudley@gmail.com> To: Jon Radel <jon@radel.com> Cc: freebsd-questions <freebsd-questions@freebsd.org> Subject: Re: why does some outgoing mail constantly end up "Deferred" ? Message-ID: <CAFsnNZ%2BncHw5ZraERNrfmCKYf_DjXqx%2BzeeEqV9_sA2z92HXCA@mail.gmail.com> In-Reply-To: <06778058-d9e5-be91-f0f8-78fa37dc6a5a@radel.com> References: <CAFsnNZK%2BR=5ROG7Gui0E61Nbox3QumZ6t1O=TzZHqq-MFQfFzQ@mail.gmail.com> <06778058-d9e5-be91-f0f8-78fa37dc6a5a@radel.com>
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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 <jon@radel.com> 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 > > <snip> > > > 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 > >
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