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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.

Google is no better. It's quite absurd, they even went through the trouble of creating postmaster tools to help you manage your reputation - except that these don't work unless you have fairly high sending rates (I forget, but I think several hundred a day). So essentially they're actively hostile to personal and small business servers.
Google is in fact much worse. Not only is it as hard to send mail to Gmail users, Gmail is a leading producer of spam.

I wish I could just wholesale block gmail.com like people used to do with the early webmail providers.

> they even went through the trouble of creating postmaster tools to help you manage your reputation

I think that implies having an actual google account to do that, which is absurd.

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

They are the reason I dropped self-hosting my mails. They were silently dropping some of my mails depending on the day I sent them. If they were at least sent to the spam folder, it would be easier to communicate with their users. And since a lot of their users are not technical at all, it's complicated to explain them the issue.

Not just email - their identity / SSO system is just as fucked
more like 98%

It's absurd in every way. I was trying to get it to stop spamming maillist traffic. It's impossible. Global level filters enacted as admin to not spam check are ignored.

Don't forget Google! Gmail will hide your email for no reason no matter what you configure on Gmail's side of things. At least Microsoft has a "please remove me from your spam lists" form (that only worked for ipv4 IP addresses last time I tried).
Yahoo were annoying and I'm happy the collapsed solely because of that
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)

I work at a big company that sends alot of emails. And even we have been put in the "bad bad books of o365 bad list", it's an absolute pain to get yourself out of the office 365 defender (I think it's what they call it now?) meanwhile your customers are complaining they arent receiving emails from you.
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Email delivery for enterprise accounts has always been more lenient, the assumption being that enterprises do have their own mail filtering software.
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?
You can usually figure that out by checking the MX records (though some spam filtering middlemen might make that hard to detect) and TXT records (if a domain imports Outlook's SPF list, it's probably on Outlook in the back).
Pretty easy to tell whether example.com uses outlook; it'll have MX records pointing there.
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).

People used to have party lines and leave their doors unlocked too, but it turns out the world is filled with bad actors and other assorted shitty people.

Email naturally followed this evolution.

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

With LLMs on the other side trying to make spam less detectable by cheap models like Jev?

It's funny when people assume benefits from some tech go one way and baddies will surely never use it...

Err we are part of a Fortune 500 and we can't even deliver to ourselves sometimes.
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

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'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".

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.
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?
> 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.

With cheaper AI classification models coming out every day now, the spam problem is on the cusp of basically being solved in every communication channel.

The only question is how many years the lazy network-effects monopolies (like Google, Microsoft, Verizon, etc) will hold this back from happening.

The optimist in me says this will unlock pathways to true decentralization of push communication protocols (like SMTP) instead of only have decentralization of pull-oriented protocols (like HTTP).

On the contrary, with cheaper AI generation the spam problem becomes harder by the day.
The power of defenders is greater than attackers here, because the defenders have more knowledge about what is "normal" for you the user.
classification != generation
Generation is, and always will be, cheaper and easier to do well than classification.

AI becoming faster empowers attackers far more than it empowers defenders. We're seeing this in every discipline and every corner of the software industry.

"Two years from now, spam will be solved." - Bill Gates at the World Economic Forum, in 2004
A bunch of my accounts were hacked a while book and since then my outlook email is getting flooded with spam. I have to give MS credit their spam filter is pretty good.

I'll never pay for email so your options are either outlook or Gmail and I don't trust Google.

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.

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.

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

I've never encountered this issue with GMail. Delivery just works. I'm trying to think of the last false-positive spam flag I've had with GMail, and I've definitely never had mail be entirely dropped.

I've had a lot of that.
> 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.

This is also true of Microsoft though.

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.

{"deleted":true,"id":50420576,"parent":50419104,"time":1794193951,"type":"comment"}
> 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.

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.

The irony is that if more people started to self host again, especially jogger companies, the problem like one exemplified by this post would be solved quickly.
Because the noise is so loud now that people are basically just coping with the stresses of work life by taking the easy path in the home life.
Because the protocol is flawed at its foundation - there is no good way to make sure that the person sending you something is a person and sending content you'd want to interact with. If the big providers weren't doing this stuff, we'd whine about the enormous amount of spam.

The solution is allow only communications that are demonstrably not spam and not unwanted.

There have been lots of proposals to this effect but maybe you have to put up two cents in a crypto wallet, which the other person can claim if the mail is unwanted. If someone takes your two cents, you remove them from your lists ASAP. The receiver doesn't benefit meaningfully from the 2c so they are unlikely to claim it. The sender is only damaged if a lot of different people claim the 2 cents. Maybe a few domains are default whitelisted even if they don't put up 2 cents, to protect against entities that are important but would be frequently spite-claimed (IRS, courts, and other similar). If you use a provider that doesn't whitelist, fine, but you're going to miss those emails.

Maybe the top 'spite claim' users are published and it becomes difficult to get people to agree to put up money to talk to you.

This reduces spam to the level of junk mail, which is still not totally trivial but is orders of magnitude more manageable.

> the protocol is flawed at its foundation - there is no good way to make sure that the person sending you something is a person and sending content you'd want to interact with.

There is and it's the same as other protocols including proprietary ones - a sender address whitelist.

There's no proprietary protocol that solved spam either.

Nearly all the spam I get has an email address from those providers.

Seems they are the disease not the cure

I'm the sysadmin at my company and we regularly get emails spoofing our own addresses! It's wild that Microsoft can't even protect customers when they have all the info to do so.
Mine isn't from those email hosts, but it from google cloud or Azure typically (not AWS for whatever reason). Related, the gmail spam filter is terrible.
Most of my spam is from gmail addresses. Why Google hasn't figured out how to stop the fake Norton renewal notices is just mind-boggling.

Lately I've also been getting a lot from compromised MS365 accounts.

>Related, the gmail spam filter is terrible.

It seems insane that gmail doesnt provide a way to automatically send a mail (eg based on domain, keywords, etc) to spam. I know theres block sender but for example aliexpress uses a different name for every email so that's useless.

I think you misunderstand the disease.

What this is called is survivorship bias. The question I would ask is how much mail are you not seeing at all because it's dropped at the edge first thing because it's IP block listed?

Next, how much spam are you seeing from them because they and Google are the largest providers on Earth? Kind of like selecting a random person from the population in the US and going "look, it's a white guy". Yea, that's how statistics works.

Lastly, because the are good at blocking spam at the edge, then that's the last bastion of attack for spammers to put their efforts in if they want any return at all.

I self-host and don't have a spam filter. Spam makes up about 1 in 5 messages I receive. It's always the same spam campaigns that would be easily filtered with a few regexes.

Self-hosting allows me to use a different receiving address for each entity I contact, so I know exactly who put me on spam lists and if it gets bad I can route that address to the garbage bin.

It's been a while since I've been an SMTP server admin but when I was I managed a few hundred thousand mailboxes under different domains. Most likely know one knows about your domain and it has little traffic. On average I saw users domains get around 5 spam to 1 ham. Of course you have outliers. I had one domain that received around 1000 spam to 1 ham. That was a domain that looked like it could belong to a university and it got absolutely flooded.

Anecdotes are not a great thing to run mail servers on, broad statistics are.

Sorry but bastions are defensive.
> frequently spite-claimed (IRS, courts, and other similar)

These entities communicate via plain old mail, that costs more than 2 cents already.

Spam is a super solved problem though and I'd rather have false negative spam than email oligarchy.
why do we cling on to the email protocol at all?

We have dozens of different ways to send E2EE messages to each other, with realtime publish-subscribe, and yet billions of dollars are spent trying to duct tape email. Who cares if Outlook/Gmail/Icloud use IMAP or Websocket? If the interface looks the same to the end user will they really care?

Why are we so willingly ceding one of the few widely used free and open protocols to replace it with incompatible proprietary ones that don't interoperate?

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

A web forum's users, who love nothing more than using the "flag" button to stomp out comments they don't like, are indignant upon discovering the world's third largest email provider has a "flag" button of their own.
Third? What's second, Yahoo? I know Gmail is first.
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.

>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

What about tencent.com, foxmail.com, or qq.com?

I don't disagree, but what are your options when a giant portion of the population uses O365 and outlook.com? How are you going to get them to stop using it, so that legit emails from user-owned servers are not silently rejected?

Most of them wouldn't even care probably...

It depends on the nature of the transaction. If the user needs the email more than you do, you just remind them Outlook deletes your messages, and they'll find a way, and in the long term usage of Outlook will decrease.
I use a sending service. I would prefer not having to, but at least all inbound email goes directly to my server.
I've also been running my own server for over 20 years, but do note that the big players may block their senders from delivering mail to your server. This happened to me with GMail around 6-7 years ago, until I configured DMARC and/or DKIM and/or SPF to their liking. As far as I know, they don't do a press release when they update their rules.
I have a perfect score in google postmaster tools on dkim, spf and 0 spam reports. They still send all emails to spam. They will even do this if you are replying to the user who contacted you. Same experience for my friend running an indie festival. These days you pretty much have to alert gmail users by some other means (like if signing up on a website) that they have to check spam and whitelist you since it appears gmail would rather block legit emails than allow a single possible spam through.
Alt take: Using a Microsoft-hosted email service is a big mistake in 2026...
That may be so, but you can't control what mail service your recipients use. So whether or not it's a bad idea, it can be your problem. That said I don't agree with OP that self-hosting mail is a bad idea.
Yes you can.

User signs up, uses @outlook. Your app declines it and explains that they block with no way to remedy, and explain they are a bad vendor.

Deeply unserious take.
Seems to work for many websites. But only if your users aren't giving you money, because it's 50/50 whether they'll use a different email address or give up entirely.
As unserious as you claim, we had this exact problem.

Emails would be accepted by Outlook.com, but would never deliver. We had SPF/DKIM/DMARC and full reporting. They RBL'ed us with no remedy.

We told the customer to not use outlook.com BECAUSE we told them we could not guarantee any delivery of messages.

Lol if you do that, your service is just going to have a small minority of people and most people will just not bother using your app/service entirely
Most people aren't using Outlook. If your users mostly are, then this solution doesn't work for you. But it does work for many people.
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.
How often would you be able to detect acceptance-but-non-delivery of your emails to office.com-hosted emails?
Always? If emails are not answered you'll usually notice unless you're a Spammer
>Always? If emails are not answered you'll usually notice unless you're a Spammer

Means you're not using your email seriously. For example, to send CVs in response to job postings.

I send up to 20 email per day to people who have issues with their package build scripts, and I have no idea whether they ignore me because they stopped using the distro or because mail got dropped.

Does it ever get silently dropped or just filed straight in their spam folder?
Silently dropped in my case.. that’s why I stopped self-hosting. Email hosting is sadly now a cartel
MS live/hotmail/outlook would silently drop - although not for this DMARC, that gets a straight bounce.
> How often would you be able to detect acceptance-but-non-delivery of your emails to office.com-hosted emails?

You should be able to see this on your DMARC dashboard

Now watch the goal post moving at light speed. This site is by business for business. They can't stand self hosting. Saas or bust. No matter how much time you spend demonstrating the opposite the next time someone mentions email they'll get a backlash. It's mind boggling how it plays out the same every single time. But give them a saas that returns the next integer for $19.99/month and that "creator" will be praised for their hard work. :)
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.

It's not enough. I have a domain that I had a very long time but it is on an undesirable tld. I got it long before it was problematic. Outlook always puts my mail in the SPAM folder even though I have done everything I could. I even deliver through a trusted provider. Not on any spam list. DMARC, DKIM, SPF all set up. No dice.
I've never had a problem not having dmarc. DMARC doesn't really mean anything. The security comes from DKIM (or SPF, but that's garbage)