Selfhosted

I'm using openbsd with dovcot, opensmtpd on a pi. I used mailhardener to get it scoring well. I've had no issues with it getting flagged.

I used to but all the tweaking with DKIM etc rules took a bit too much of my time. Now I'm using Zoho Mail to host email on my own domain.

I run my own email server using Mailcow. It works well.

However, I do not even attempt to directly send outbound email. It's very difficult to get your server trusted by the major providers, especially Microsoft (who are very picky about email servers). I have an account with MXRoute (which is an email provider) but only use it for outbound relaying. Inbound emails go directly to my server.

For what it's worth, MXRoute is a great provider to consider if you want to move away from the large ones (Google, Microsoft, etc) but don't want to self-host.

E-mail was the first "thing" that got me off of Google (to Proton & then currently Tutanota) but is really the last remaining service I not have self hosted.

I have always read about how difficult and time consuimg it was to run your own mail server, but I felt like I needed to experience it myself. So I purchased another domain and followed the instructions on https://mailinabox.email/.

I am using a small VPS on Hetzner and I have to say the experience has been almost flawless so far. I did need to have my new domain taken off the Domain Block List, but Hetzner gave me a clean IP and defaults to blocking port 25 outbound to prevent spam (simple ticket to open, once account is 30 days old and paid).

I know I'm still early into this journey so far, but it has been really simple and I plan to test this secondary domain for a few months before moving onto it full time.

As an avid self hosted of literally everything else, I can say it has been a lot of fun learning so far!

I did but I stopped. My server had everything set up (DKIM, DMARC, SPF, Spam filtering) but I gave up after some providers wanted me to jump through hoops to get my mail delivered. Also I never had enough outgoing mail to build some reputation.

Not likely worth it. Primary reason is that the large federated email services are skeptic also of email from services such as your proposed self hosting solution and may simply not deliver the mail you send. This is to mitigate against spammers setting up a bespoke servers.

There are a bunch of other things that could go wrong if you don’t set everything up perfectly, but even if you do, this would be a big problem.

Better off using a custom domain with a big provider. Fewer headaches. I like Fastmail, but many others are great too.

I use https://github.com/docker-mailserver/docker-mailserver with sendgrid.com as an SMTP relay (recieving emails is easy, sending them successfully is a pain)

I don't. But I do have my domain and use a hosted solution, so I'm kind of independent and own my data.

Very interesting. Thanks for the follow up.

I want to do a setup where i use mailcow at home for receiving emails but Amazon ses SMTP for sending, it's possible? Looks like it is, but i didn't investigate it