Using self hosted email service is a big mistake in 2026.
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.
Alt take: Using a Microsoft-hosted email service is a big mistake in 2026...
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.
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.
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.
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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.