45 comments

[ 243 ms ] story [ 1487 ms ] thread
I've had this exact problem for years. My IP addresses have been used for 15+ years for sending e-mail, they are spam-free, but Microsoft keeps blocking them. Every two months or so I have to ask them to unblock the IP again, then I can send mails to Outlook again, until they just random decide to block me again. It's an absolute clown show.
This is the price every small sender pays. The unblock request process is essentially designed to make you give up or move to a large ESP. There's no appeals process, no SLA, no acknowledgment that your reputation data might just be wrong. You're at the mercy of a system that treats false positives as acceptable damage.
I created my first Outlook account when I was young. Now, 30 years later and its still my primary account. I can't imagine how I would migrate to another email address if Microslop would begin ruining Outlook by forced subscription or something. My digital life is in M$ hands at the moment.
Act now.

- create a new email address somewhere else, preferably with your own domain

- redirect all your emails to your new account

- send an auto reply: "I don't use this email address anymore, and I may not see this email. My new address is XXX"

The third point is a lie that nudges people into updating their addressnook a lot faster. If you just silently redirect they might not even notice. But you can explain in a sentence why you are doing this.

This redirect+auto reply can be left in place forever.

Adding that ideally one would only auto-replay to people in their address book at the time so one is not replying to spammers.
It feels like there's quite a lot of spin on this. There's no hint as to how many users were actually affected. It only really seems to mention Estonia, and probably only a region of it.

The ISP there claims they haven't received any reports of SPAM. But that sounds wrong. No reports probably means your reporting system is broken.

So putting that together, it seems like a small ISP screwed up and let spammers go wild, and Outlook blocked them for it. I can't really fault Outlook for that.

This is an extremely widespread issue. I send close to a million emails per month across dozens of different providers (all newsletters.) These are all from high reputation domains and email accounts. We are completely unable to make anything happen with Microslop. It is infuriating.
Your intuition is way off, like dangerously off. But your comment is a great example to show a smug lawyer at Microsoft when they try to say there is no basis for the claim that these blocks against legitimate senders are defamatory.

This has been affecting reputable senders who take spam reporting seriously, including MXRoute and Discourse.

> No reports probably means your reporting system is broken.

"No reports" can mean a lot of things. There is no "probably".

The "you" in "your" is Microsoft because under a certain volume of email, they don't even send reports. I regularly test the abuse contact address for my server because of this exact unfair assumption - that it must be my fault. I have never once gotten an abuse report notification from Microsoft, but I have gotten a bounce message saying that I'm blocked because I apparently send spam! Btw, this was in reply to an email from a Microsoft user.

Worse, I figured I'd just disallow any email from a Microsoft property - if an outlook (or hotmail or live or anyone else) sends an email, I can just bounce it and tell them to use a different service to reach me since I can't reply. Nope! Microsoft won't surface the bounce message to the user.

So, I am barred from replying to Microsoft emails. I am also barred from informing the sender that their email won't reach me.

It's defamation - the sender is always going to assume that it is my fault if I didn't reply even if the reason I "didn't reply" is outside of my control.

> So putting that together, it seems like a small ISP screwed up and let spammers go wild, and Outlook blocked them for it. I can't really fault Outlook for that.

Yes, in your imagined scenario, you can't really fault outlook. In the real world, however, outlook is very much to blame.

One IP address (exclusively ours) among our email IPs at my place of employment was affected. We have used that IP for nine years. Emails are strictly transactional (receipts, password resets, et cetera).

The "rate limiting" started two weeks ago, giving us a code that Microsoft's documentation doesn't even list. It remains unresolved. Never had critical issues like this on our transactional IPs prior to this, and this particular IP address is still delivering just fine to other consumer and corporate email systems.

Everyone who runs an email server knows Microslop doesn't care about receiving its customer's emails. The best thing you can do is migrate away.
It's has been like this for a long time. For me hotmail is unusable because some emails just never arrive due to their spam filtering.
I’m guessing they connected CoPilot to the inbound filter and it is doing stupid and unexpected things.
I wonder if Microsoft actually likes running their free email service still. They wiped a ton of old Hotmail and Live.com emails some years ago (and then allowed new people to register those deleted names). I imagine they don't get much out of it anymore.
I'm in the privileged position to advise clients to move away from hotmail/live if they want uninterrupted email delivery.
Just had a friend reach out yesterday about this issue. His outlook account for 10+ years started having issues receiving emails from his dad and a company he works with.

All I could find was that his dad’s email was missing SPF/DMARC but the other email address that was having problems looked like it was configured correctly.

I only was able to get a screenshot of the email voice his dad received and it mentioned being on a block list (like in the article).

I've stopped diagnosing outlook/hotmail/live delivery issues about 12 years go, they simply do not give a single fuck about their customers. It used to be different, about 18 years ago orso, they had ways to contact them and resolve such issue.

fuck big tech :)

My clients have been experiencing this forever; the logs SAY "temporarily rate limited due to IP reputation." but really the emails are never going to get delivered. I have to get MailChimp or Mailgun to rotate the IPs.

It looks like all it takes is one person to mark your email as spam, even by accident. Note that these are mailing lists which they signed up for in MailChimp case OR transactional emails in the Mailgun case.

It's only hotmail/outlook that we constantly have this issue with, Google etc. are all fine.

Agreed. I was an early outlook.com user (was working at MS when it launched, I think internal users got slightly early access allowing me to claim a nicer name than my Gmail) but despite having well over a decade of accounts tied to it got so angry at certain messages never appearing that a couple of years ago I reversed the flow of forwarding and swapped to another account as my primary.

Sounds like it's gotten even worse.

(comment deleted)
As long term Outlook.com user all I can say it's their service is extremely unreliable, my emails are either not delivered at all or end up in junk mail, some emails I don't receive at all or my partners are rate limited sometimes receiving their emails with hours long delays.

I assume also their junk filters block some emails and there is no way to avoid it, you repeatedly add senders to safe senders list, even to safe subscriptions and their email still end up marked as junk even after years long communication from same addresses.

As backup when something important I write email to recipient from gmail whether they received my email from outlook only to find out my email was never received.

A few years ago, in my university we have a big problem at the beginning of the semester to contact ~10K students, in particular when they register to our Moodle platform and the server sends them a message.

Gmail was usually ok.

Yahoo had some max messages per day.

But Hotmail/Live/Outlook/whatever just made the messages disappear, no spam folder, no bounce, just disappear. We had some success telling the students to send us a message from their Hotmail/Live/Outlook/whatever address half an hour before registration. This adds our address to some special secret list for that account, and our later messages (usually) reach them. (It may fail. It may fail. IWOMM. YMMV.)

It's not just Outlook, it's all MS email products as well as Yahoo.

These are emails that our customers have specifically requested and we get support tickets blaming us.

It's been like this for years.

I was unable to reach a business this week who host their email on Office 365. Any email I sent would bounce with:

  550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)'
For context, I was replying to an existing and very mundane email thread.

Something is rotten in the state of Outlook

This is one of those articles that demonstrates why email should be distributed. Letting Google and Microsoft run email for the planet is just asking for problems. There are some technical demands to running email services, but they are still in reach of the technically inclined individual or organization. If for no other reason, it would help keep the big mail service providers honest.
microslop should start focusing on real world problem than overhyped ai bubble.
(comment deleted)
It is my experience, that Outlook is not a reliable e-mail service. Sometimes e-mails are not delivered, or only delivered hours later. When they are delivered, even as a paying customer, they are downloaded so slowly, that I had to wait 10 minutes to get all my e-mails, while my 1 EUR per month Posteo provider delivers in seconds.

My impression is, that the only reason one would want to have MS as a mail provider is, that they are entrenched in the e-mail provider reputation and delivery game. Other than that, it seems to be an all around bad service. Not even talking about the mail client itself.

I was using outlook for communicating with businesses as it is often what they use. Some of them just could not send a response back to me, so I am not using outlook anymore. Just normal Microslop stuff
Having to explain to customers that they didn't receive an email because Outlook has a multi-stage set of email servers and the inside ones reject due to the edge (antispam) servers is always interesting.
Very happy I decided to ditch outlook (and did it) this year after 10+ years. Every other year some part of the system would break, deliverability, authentication or 2FA. More ads, less value.

Eh. Another product driven into ground by Microslop

Days since last Microsoft fuckup: 0 (hard-coded)