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I've been running my own email since forever (and over UUCP before that) and always considered it easy too. However starting this year I'm paying for an SMTP relay so my outbound mails share transit with other relay users', making them less likely to be IP blocked by Microsoft.

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I got blocklisted by Microsoft one time, I filled out the following form, it was cleared in a day or two, have not seen any issues since.

https://support.microsoft.com/en-us/supportrequestform/8ad56...

sounds like a good solution, can you share a few details?

I use Postfix for SMTP. Inbound emails arrive directly at my server without any intermediary. Outbound emails use Postfix sender_dependent_default_transport_maps, which routes outbound emails via mailgun. I use this method because I host multiple domains and it lets me use domain-specific credentials with the SMTP relay. Outbound routing could be done using the same credentials for all domains but that causes some unnecessary pollution in message envelopes.

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