Bob Proulx wrote:

No matter what you do on your end there is no way to guarentee that
the large mailbox providers will accept the <del>forwarded</del> messages.

FTFY. :(

Because at any point in time any of those users might click "Spam" on
the message.  And there is no way you can prevent this.  It's a human
problem of human training.

It's not even about forwarded mail, or spam.

I'm plugged in to Microsoft's "Junk Mail Reporting Program" for mail coming from both our outbound cluster and forwarded from our MX cluster.

End users on Hotmail/Outlook.com routinely mark *legitimate direct messages in ongoing conversations* as spam. They report *legitimate government communications about something they've asked a government office about*. They flag *mail from their lawyer*.

I can only guess that the "Mark as spam" button looks a lot like a "Delete" symbol of some kind, or I have to give up all hope of intelligence on the part of end users.

My experience is that if it is Microsoft that they will allow one free
black eye for you.  I contact them and say, hey, what's the data for
this so I can improve things?  What message do you have in the corpus
of evidence for me?  I want to figure out what is happening and stop
it.  They write me back and say, "Don't talk to me you spammer.  We
will show you nothing.  But we will delist you this one time."
Obviously this is a paraphrase from memory.

Now delisted things work okay again for a while.  Then for reasons I
have no idea there suddenly Microsoft rejects all mail again.  I try
the official contact channels.  Now they go, "Don't talk to me you
spammer, you are a repeat offender, we are not going to show you
anything, and we are not talking to you again."  Paraphrasing again.

Or they refer you to their rules for "bulk senders", which are variously inapplicable or utterly irrelevant for both forwarded mail and ISP-type outbound relay mail flow.

I have yet to see any evidence from Microsoft as to what messages they
think are worthy of being IP blocked regardless of my attempts to
communicate with them.

If you can get recognized as a suitable contact for your outbound IPs with Microsoft's SNDS and JMRP you can start seeing (some of?) the mail marked as spam. It's helped us locate low-volume compromised accounts now and then.

If you get IP-blocked, you're sending/forwarding "too much spam" (whatever that means), and in the end it may just come down to telling your users they can't forward mail to Hotmail accounts any more as a matter of policy.

  Therefore I have no way to improve processes
on my system.  I am thinking one of my users is forwarding and then
reporting messages as spam.  But without data I can't be sure.
Without data I have nothing to grip upon.  I don't know anything firm
about who or what.  Eventually I am forced to route Microsoft
destinations through a different IP address to avoid the IP block.
They have the might and I do not.

Sometimes it seems like they're blocking because it's a day ending in y.

-kgd

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