Thanks Al! Jeff also reached out to me off list and offered some pointers along the same lines. This looks like good solid advice for anyone dealing with the same.

On 2021-07-27 18:34, Al Iverson via mailop wrote:
Microsoft is the mailbox provider most likely to block, that's for sure.

I'd probably suggest trying again with Sender Support and focusing on
a pre-emptive accommodation request:
https://www.spamresource.com/2021/05/requesting-pre-emptive-accommodation.html
That's basically telling them you're doing IP warming. They'll
respond, asking you to give them a grid of dates and target volumes
and they'll in theory raise the limit of how much you're allowed to
send accordingly.
It also couldn't hurt to tell them that this is a new IP range for you
-- that's another factor they'll consider, I think.

If you've done that and they're still blocking, I'd suggest pushing
back hard on sender support, explaining that you did this already and
they perhaps ought not to be blocking what they were already warned
would come.

They're also quicker to block if the volume is spikey and uneven. Make
sure it's as even as possible, limiting volume by day as you build up
that reputation.

Then of course the other question is always, is the mail really
wanted? You sound like you've already got that bit under control, but
could your segmentation be incorrect? Perhaps you're allowing types of
mail or an amount of mail that you did not intend to.

Good luck.

Cheers,
Al Iverson

On Tue, Jul 27, 2021 at 4:56 PM Jarland Donnell via mailop
<mailop@mailop.org> wrote:

I'm hoping someone here might be able to offer some thoughts that I'm
overlooking. So I have a /22 that I use primarily to deliver customer
emails. We're an ESP, customers bring their own domains. I've been using the first two /24s of the space for a while, but I'm trying to slip the
rest of the /22 into production. My plan was to do it slowly, so as to
not set off fire alarms at Microsoft, Verizon, and AT&T. However, I'm
only using one IP from the 3rd /24 so far, and I still can't get this IP
warmed up with Microsoft.

I'm at least two months into solid usage of that IP, and Microsoft is
still rejecting every mail from it with:

"550 5.7.1 Unfortunately, messages from [136.175.110.3] weren't sent.
Please contact your Internet service provider since part of their
network is on our block list (S3150). You can also refer your provider
to http://mail.live.com/mail/troubleshooting.aspx#errors.";

I'll turn around and deliver the same message from 108.0/24 or 109.0/24
and they'll accept it with no issue. They've given me temporary
mitigation at my request, it's expired and we're still doing this over
and over again.

Now I do filter outbound email heavily. Obviously customers use email
forwarders and some of what gets through isn't great, but it's not like
I'm flooding their servers with junk. Most of this is direct personal
emails between my users and theirs. There's no abuse complaints coming
in from MS, SNDS portal is as clear as can be. I'd argue that I'm the
most militant ESP when it comes to preventing outbound marketing, I'll
nuke a bad actor from orbit within an hour and everything is monitored
by human eyes and automation 24/7. Password compromises rarely make it
beyond the "testing the credentials" phase. All around very clean
outbound. And yet, here we are.

What do the rest of you do to warm up a new IP range with Microsoft, and
have you ever found yourself months into a new range with nothing to
show for it with them?

Jarland
MXroute
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