[randomString1]

Email is already fucked. In my experience Gmail often failed to receive emails from services like Yandex and Zoho. Plenty of people here that setup their own servers, and know what they are doing, getting randomly blacklisted.

Maybe it's fine if email is not central to your life or business but if there's even a, let's say, 10% chance of my emails not getting delivered to Mr Google I have no other option than to bend the knee.

[username223]

It's a tragedy. The people who designed SMTP went to insane lengths to make sure mail was delivered. The people who initially implemented it did the same. Then the "free" mailbox providers fucked it all up. I host my own email, and I now have no clue as to whether it will be delivered.

[kuschku]

On the other hand, I’ve had only good experiences with self-hosting my email.

I’ve never had issues with being blacklisted or anything.

But I’ve been sending with SPF + DKIM + DMARC + ADSP all configured and enabled since day one, and with TLS transport for all sent emails.

That usually gives a major boost in trustworthiness.

[megous]

Unless your IP address is deemed being in a bad block. Then all of the above is not even checked (on outlook.com, that is).

[CaptSpify]

This matches my experience as well. I rarely if ever get sent to a spam folder. And afaik, I've never been blacklisted after ~5 years.