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Outlook.com is also rejecting mail based on blocklists that are not public and you essentialy cannot get yourself out. My VPS provider is pretty much entirely blocked and their regular blocklist process says we are golden so nothing to unblock.

Outlook.com and similar are an anathema to email. This is why they tell you not to run a mail server .

On the other hand rejecting domains without dmarc is fine. Just not happy it is silent.

Everybody I know who still runs their email server (you can get Europeans out of Europe, but you can't get Europe out of the Europeans) complains about Microsoft.

I bet Microsoft is single-handedly responsible for 80+% of complaints about email being impossible to host.

In a federated / pseudo-decentralized network, any provider with 10+% of captive users has an outsized leverage on the entire ecosystem. You don't need a monopoly; as long as you have a monopoly on just a few users that others absolutely need to be able to interact with, you can dictate terms to everybody.

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Same experience here. We have multiple customers whose servers are in large blocked IP ranges, with seemingly no way to get them delisted. The strange thing is that Microsoft only seems to reject their emails on Hotmail/Outlook.com accounts (free accounts), while accepting them just fine on business accounts. Meanwhile, their “support” tools tell you there’s nothing wrong.

Based on my broad experience, I’d comfortably rank Microsoft as the worst of the major email providers. (I am owner poste.io)

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outlook.com and O365 are horrible to deliver to. We regularly get issues where we sent an email it was accepted by O365 but was never delivered to the mailbox. We have one person working at least half the time on resolving stuff like that. And that's from a respectably maintained SES egress with good reputation, DMARC, DKIM configured.
There is a trick. Sign up with them, configure custom domain, but don’t set your MX records. On your MTA, route mail that goes to Outlook/Hotmail to go through their MSA with your Outlook credentials and headers stripped as if submitted directly by user. Outlook gets mail through their own MSA it trusts, rest of the world talks to your mail system directly. Replies still go to your MXes.

I haven’t productionized this setup (I send maybe a dozen emails a year) but it worked for me ad hoc a couple years back, when I had to send a mail to an Outlook-hosted address and they blackholed everything I tried to send while 250 OKing me.

The problem with this setup is that if I want to send email to fred@example.com and example.com is actually handled by Outlook, I need to somehow know beforehand that email to example.com needs that special routing. Or do you just route ALL your outbound email through Outlooks MSA?
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I have a small client with a large email list who wants to switch from once a month constant contact newsletters to sending them through SES with a self-hosted Sendy instance. This seemed like a reasonable way to save $10k a year or so. I haven't used SES before for anything. I have run an email server for 30 years and had occasional blacklist headaches, but it's not used for mass mailing of that sort... it's usually several years between problems. Is this a terrible idea to switch, even if it's off a "managed" SES dedicated IP? I don't want to switch them and find out no one on Outlook is getting their mail.
What's the nature of your operation? If they're not giving you money then you're within your rights to say "sorry, don't use outlook"
Our customers are giving us lots of money. And the nature of the emails are account reminders, activation and internal message notifications.
Usually they are giving you money...

I ran a SaaS up until recently. Emailing users notifications for events was just a normal part of the app. Users got upset when the emails didn't come through. So then I had to be email tech support for something I had no control over. Lovely.

Funny, they have no problem handling mail for essentially every Fortune 500 company and others large and small.

It's always people self-hosting mail on a shared server in Moldova (because they think it makes them cool) that are complaining.

Self hosting mail on a shared server in Moldova is basically the entire idea behind email (and the internet).

Which with cheap models like Jev as spam classifiers, this can now become a reality.

The problem is, Google and Microsoft have monopolized the entire email market, so their esoteric deliverability mysticism from 2007 still persists (basically blanket bans on entire IP spaces, locking out anybody trying to send emails on their own).

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Nope, people self-hosting mail on their own hardware from their own basement in Serbia ;)

https://www.mimar.rs/blog/a-journey-of-my-mx-server-to-new-r...

And yes, it's cool not to have to let scum read your private communications :D

Err we are part of a Fortune 500 and we can't even deliver to ourselves sometimes.
Maybe because every Fortune 500 company (and 99% of all large companies / orgs worldwide) uses O365 / Exchange / GSuite?
> Outlook.com and similar are an anathema to email. This is why they tell you not to run a mail server .

It should be the other way around though.. More people should run their own mail servers so that centralized players cannot control what should be a decentralized communication protocol.

I had experience implementing and debugging mail delivery, so when I chose to run my own server I just opted for a SMTP relay, and never had an issue. I don't know why this isn't the recommended default solution.
I've had several times where mail from custom domains associated with a business were delivered hours late by Outlook. Time sensitive emails. A guy coming to my office for a meeting called me and said he was downstairs and having an issue with security. Went down and swiped him in.

Four hours later, I got the same message by email. I thought he was back - nope. An email sent at 10am that was delivered at 4pm showed it was from 2pm until I looked at the header and saw sent at 10am and just... chilling out for 4 hours. DMARC was set up for them just fine.

I've had the same issue with my own custom domain, with DMARC set up. A year later, it finally got bumped up to some sort of "trusted" domain for that one place and my emails get delivered the same day now.

Got a similar issues with outlook. Emails from some websites were delayed by several hours.

Mildly infuriating for emails containing OTP codes "valid for 10 minutes".

Is it SNDS (https://substrate.office.com/ip-domain-management-snds/snds) you refer to as their regular blocklist process?
yeah I see it for them being a problem too if they are not accepting legitimate email. I might be a bit stubborn here but I refuse to give them the monopoly and self host our email anyway. I just wish more people would join this fight
Pretty sure this or part of this just burned me. Icing on the cake is Nintendo will also ban hammer your email if it rejects some or all of their emails - including their dumptruck of marketing junk. The only and I mean only resolution to this is to basically move your Nintendo account to a different email completely. Absolutely unreal on both sides.

Yes, no one should not have DKIM or DMARC but holy yikes when neither side wants to actually give in to help the customer.

I was viciously mean in my communication with the Outlook team when they said they “couldn’t” remove me from the blocklist. I pointed out that, as the operator of a perfectly compliant secure server their inability to deliver my mail is a technical failure on their end and one which I will be contacting their supervisor about and they somehow managed to scrabble together the heroic ability to delete my row from a table. Never back down from these bastards.
Which VPS provider out of curiosity?
Maybe don't self-host mail on a shitty $1/month VPS where 99% of the tenants are spammer scum?

This is not Microsoft's fault. The building's on fire and they're locking out the arsonists.

Requiring DMARC may be good, but Outlook's approach is awful.

I was working for Microsoft when outlook.com launched and got a good email address that was my primary for more than a decade.

I had so many issues with things getting silently dropped with no recourse (2FA codes, account recovery mails, etc.) on so many sites that I finally gave up, reversed the stream, and had Outlook forward to GMail instead of vice versa. A few months after that, I realized that all my Outlook got was an enormous volume (hundreds of day) a spam and that all legitimate mail was going to my other accounts, so I turned it off entirely and haven't read that mailbox in over a year.

> I had so many issues with things getting silently dropped with no recourse (2FA codes, account recovery mails, etc.) on so many sites

This is not unique to Microsoft and really the source's problem — they did something to get blocked in the first place.

Add in the fact that you're almost certainly not the only one impacted, and that they have no interest in fixing it, it screams incompetence on the source's part.

Been there, done that, good luck explaining the problem to the app's first-level support in the Philippines because it's not in their script.

> and had Outlook forward to GMail

Till the day GMail hits you with the "We couldn't verify it's you" bullshit and locks you out of your account forever. Good luck getting support from Google, the word is not in their lexicon.

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no matter how much you pay for VPS or which cloud you use you'd get same treatment

Stop being so ignorant

Some hosting providers are known for not caring about the activities of their customers, but in general, how would I know that the other tenants are scum?

I have access to a fairly large dataset of known bad hosting providers, but most people don't. So how do you tell the difference between getting a good deal and "this is cheap because it's sketchy as all hell".

We also don't block all of Vietnam, or all Jio customers in India, even if we know that 20% of bot traffic is from those two alone.

> This is not Microsoft's fault.

Wait until this guy realizes that all spam these days comes from Azure ASNs, and abuses cross-tenant issues as well as a simple "Fwd: ..." and "Re: ..." tricks to bypass Microsoft Outlook spam filters.

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> Outlook.com and similar are an anathema to email. This is why they tell you not to run a mail server .

It turns out that whoever has the most power is the most powerful. This is why distributed/decentralized systems cannot singlehandedly free us from tyranny, and why I find people who spend all their time preaching decentralized systems to be quite silly. We don't need better systems (well maybe we do but,,,), we need better education and awareness of how billionaires manipulate us; this goes beyond software.

Complain all you want about the monopolists, and I do think you're right to do so, but a lot of their power comes from and is aimed at defeating the overwhelming flood of spam.

Mail, then emails, then home phones, then cell phones, then texts, then social media have been gradually rendered less and less usable by bad actors systematically abusing every single tool we try to use to communicate with one another to steal from us, lie to us, and manipulate our beliefs, and we'll just keep inventing and discarding new ways of communicating until we reckon with this.

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I don't think anyone believes it will "singlehandedly free us from tyranny", it's one component for a healthy ecosystem.
Decentralization is not a bulletproof solution. It is a mitigation. Until someone gets 50 percent of market share. Then they can run havoc on the ecosystem with their own customized system.
We could tax billionaires and use the money for a Manhattan Project to stamp out fraud, abuse, and corruption.

But we won't.

>we need better education and awareness of how billionaires manipulate us

So that people would vote for the government to manipulate them instead?

Honestly, I hate outlook as much as you do, but I'd still prefer it to Max

https://en.wikipedia.org/wiki/Max_(app)

Just put codex in a continuous goal loop to keep you off the blacklists...give it whatever email / creds it needs to make the appropriate requests and make the needed changes (ofc tell it the guardrails it should follow).

Selfhosted email is likely easier now than it ever was before.

> give it whatever email / creds it needs

Oh man, please tag me if you're ever the lead on any project so I know to stay far away from it.

Using self hosted email service is a big mistake in 2026.
Why are we so willingly ceding one of the few widely used free and open protocols to a handful of $mega-billion providers?

Experience shows that the walls will get taller and the moats will get deeper.

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Sounds more like using outlook.com is a mistake. I've been running my own mail server for over 20 years and outlook.com is literally the only domain I have had problems with, and this is the only reason that I now send via Scaleway's free transactional email service.

The people working on outlook.com are just talentless amateurs - the rest knows how to do it right. It's a shame it's so widely used.

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Alt take: Using a Microsoft-hosted email service is a big mistake in 2026...
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You can take my email server from my cold, dead hands.
Proudly self-hosting since 2001. My mail server is in my basement. Do not know what you are talking about.
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This is what google and microsoft want the make you think for obvious reasons.

Fortunate for those running their own servers is that they actually still get all the cool emails from people not complying.

Why?

At the most you need to use an external service for delivery (usually because you have problems with MS) but you can still run your own server with no difficulties once you do that.

That said, DMARC is required by a lot of people now, so I do not think this particular issue is a problem.

I have been self hosting my my personal email (and for family). Few problems so far other than delivery to MS and I have recently moved a domain I use for work email over.

Oddly enough the MS problems come from hotmail, but not other services. If that is a problem, then pay a bit to have email delivered.

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