Long delays on incoming email from Office365/Outlook.com server farm

[balza...@gmail.com]

I'm running Sendmail 8.14.4 via Debian's 8.14.4-4 package. We're seeing extended delays in delivery with email originating from OUTLOOK.COM servers.
I have an example set of headers plugged into the MX Toolbox here

http://tinyurl.com/kjjoeqs

and a copy of the complete headers here

http://pastebin.com/MLUgZwwf

on a message that came some 5+ hours after it was sent.
We do use milter-greylist-4.3.9 and the "Delayed for 14:38:52" message is completely confusing to me, especially since mail.log indicates this message was delivered within 11 seconds.
Anyone have any clue as to what might be causing these delays in delivery?

[balza...@gmail.com]

I've posted the complete entry from mail.log for this message at

http://pastebin.com/FGpvGzfA

in case that helps.
I'm very grateful for any help/hints anyone can find time to offer!

[Bruce Esquibel]

balza...@gmail.com wrote:

> on a message that came some 5+ hours after it was sent. We do use
> milter-greylist-4.3.9 and the "Delayed for 14:38:52" message is
> completely confusing to me, especially since mail.log indicates this
> message was delivered within 11 seconds. Anyone have any clue as to
> what might be causing these delays in delivery?

No, but I don't think your log reporting is complete.

You do know what grey-listing is, right?

When the initial delivery attempt was made, your box gave them a 4.x.x error
telling it to "try again later". Most normal systems will try to send it
again in 15 or 30 minutes, over and over for 5 days.

But since you are dealing with Microsoft here, their idea of a "try it
again" might be 5 or 6 hours, if they try it again at all.

We quit using grey listing for that reason, too many fucked up mailers out
there and too many user complaints to deal with.

The grey list package should have some kind of whitelisting file to work
with where defined mailers (usually by ip address) can be given a skip this
check because they are trusted.

But unless you are running a mailer for yourself, grey-listing just isn't a
good option to use. Too many spam sources hiijack mailers which do comply,
so it's ineffective there and like I said, too many crap "business" mailers
don't comply and legit mail gets bounced back.

-bruce
b...@ripco.com

[balza...@gmail.com]

I appreciate the response!

Man you aren't kidding when you say Microsoft only uses the RFC as a suggestion.

Turns out, if you configure greylisting very specifically you can make an allowance for Microsoft's wanting to make things up as they go along. For milter-greylist the answer is the additional configs I list in a post to their list

https://groups.yahoo.com/neo/groups/milter-greylist/conversations/messages/6506

Which I hope will be of some use to any sendmail user who greylists and has the same issue.