[2Gkashmiri]

i installed MIAB like 3 years ago. had this exact same problem with outlook at the time. did the same and never have had any more problems.

last year i helped someone install miab and somehow neither gmail nor outlook nor any "major" provider logged them as spam from the get go. i was truly impressed and surprised.

i have heard war stories about people self hosting email and having problems. sure 3-5-10 years ago that might have been the case but not now for the most part.

please give your self hosted email a try again. it will take you less time to set everything up than cooking dinner. try using miab or similar email software.

go cheap, like racknerd or something and save money from vultr/DO.

[SXX]

Just keep in mind that you need working reverse DNS record and not all cheap provides support it. Also cheaper hosting solutions usually have worse IP reputation.

[9cb14c1ec0]

Saving $1/month is not worth email delivery problems.

[freedomben]

You may have gotten lucky with IP addresses. When your cloud provider gives you an IP address from the pool, it is luck of the draw whether some customer in the past got that IP address on the bad list with some mail providers.

I strongly want what you say to be true, and would also encourage people to self-host email, but I want to make sure people are aware of the pits so they can avoid them or at least not have to learn the hard way.

[account42]

With Microsoft a clean IP is not enough IME - you also need the whole block to be clean. That's not really something you can control if you have just the one IP.