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.

Indirect reference to this recent thread: https://news.ycombinator.com/item?id=47230704

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).

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.

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.

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.)

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

It's been like this for years.

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 even went as far as signing up for Azure, in the hopes that if I sent from a Microsoft IP it might not get blocked. But I didn't make it very far, every step of the way was like watching paint dry while the interface loaded or did something. Once I finally got the thing set up in order to send mail, the API was so molasses slow that it couldn't handle our mail throughput. Meaning it would take about 30 seconds to send each transactional email because of how slow their API is. Well that's only 2880 emails per day, that is not a reasonable send rate at all.

I have even lost customers over this mess, it's really hard to explain to them that they can't receive our email because of their provider and not us. Especially when Microsoft has the audacity to return: 250 OK Email Queued (but then not deliver it anyway!)

If anyone has any solutions to this mess I am all ears!

Otherwise there’s no incentive for the big providers to care.

Similarly for anti-virus. It’s a PITA when Windows or Mac falsely flag a program as a virus when it’s not in their app stores.

Now I only use Windows for legacy software that my customers force on me.

Fedora has not just been liberating, but jaw dropping. I actually felt offended that I had wasted so much time on debian-family/ubuntu/mint and windows.

How many users would you see as the threshold then?

Since you stated that there is a spin to this, how many users would go over your defined threshold level?

UPDATE: After a bit of digging it looks like they started the username recycling policy in 2013, may have quietly stopped doing that in 2018 but formalized no longer doing that in 2021: https://web.archive.org/web/20230627104616/https://www.micro...

"Summary of changes to the Microsoft Services Agreement – June 15, 2021 [...] In the Outlook and Office Services sections, we’ve removed the Outlook.com section to clarify that an email address or username is not recycled into our system or assigned to another user."

Outlook.com certainly has to show up as an expense, one that Microsoft would like to reduce. When you look at what other providers charge for a single email account, it's hard to see Microsoft making money of Outlook.com. There's obviously something to be said for scale, but still, it must cost them something.

I blocked off Zendesk entirely because they didn't fix their shitty email system. The other newsletter mail services (mailgun/sendgrid/etc.) are just as bad for this.

There are plenty of reasons why large email senders could (and should) be on reputation blacklists. None of these email delivery companies seem to care very much about the spam they send until shit hits the fan, and now that it did it seems everyone blames the people maintaining the blacklists.

Just like Internet Explorer used to be the program you used once -- and only once -- to download a proper browser.

Sounds like it's gotten even worse.

Once enough of your customers do this to cross a certain threshold, you are identified as an undesirable sender and QED.

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.

Weird trick to get unblocked: follow the standard three-email procedure to sender support, then send a fourth email ccing [email protected] telling them to unblock or next step is attorney general.

The thing about a lot of attorney generals is they LOVE to smack down a big corporation like Microsoft for the little guy.

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.

- 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.

That should allow you to be more proactive about users reporting your messages as spam, either intentionally or unintentionally.

FWIW: We've been sending Microsoft properties e-mails for over a decade, fairly small scale (maybe 5-20K unique recipients at MS properties in a month), and every 2-4 years we have to submit our IP to their "whitelist me" site and then we're golden again.

This time was different, when we submitted our IP to the whitelist site it said "Nothing is blocking your ability to send to us". They did end up responding to our whitelist request a week later asking if we were good or still needed help, which is a first.

I know for a fact my mail server never sent any spam because I logged everything. It was only me using it. But every few months I got banned from sending to live.com. I have one friend there. They didn't mark anything as spam. We just sent personal emails.

There's a form where you can unban it but it kept happening. In the end I stopped running my own, it was so much hassle.

Imapsync is your best friend for this, as far as syncing the new account with the old one.

https://github.com/imapsync/imapsync

https://imapsync.lamiral.info/