this post was submitted on 15 Dec 2023
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Absolutely, Outlook.com is by far the worst in this regard. I stopped running my own mail server a few years ago because it was just unbearable.
Are you using a residential IP? There are lists of residential IP ranges for mail servers to block, no matter how well configured.
Hm, I thought hosting providers should be fine unless you just happened to get an IP in a block that some spammers also used to use... but then again, I stopped self-hosting email several years ago because of all the hoops one has to constantly jump through (for reference, it used to work fine from Online.net's —now Scaleway— bare metal servers, like 5 years ago).