[jankins]

I've been self-hosting for the past 4 years and this hasn't been my experience. Things like fixing DKIM/SPF eat an hour or two occasionally, but I've never encountered an issue where the time investment overtook the learning + other benefits - it's been hands-off 364 days of the year.

I've only seen one blocked send happen -- blocked by my grandma's @att.net account. Since it happens so infrequently and nobody uses @att.net, I just re-sent from a Hotmail account instead. No issues with the other major players. But for my use-case it's easy to mitigate and if the problem persists I can invest more time in it, but one recipient blocking me in 4 years isn't bad.

It's the only way to have ownership, which is is one of the benefits I really like - Google, Yahoo, etc. still get pieces of my personal email history because nobody else self-hosts or uses PGP, which is disappointing, but I prefer it over handing one player ownership the full history.

BTW, I'm running it on the same 512MB DigitalOcean droplet that I use to host my static sites (personal website, small product sites, etc), so it's basically free since I'd need to host those things anyway, which is nice. Needs some swap though.

Edit: Not saying these points are invalid. They're certainly valid, a service like Gmail _will_ be more reliable and easier. If you're blocked for some reason or have any other email probs, there's nobody else to fix it besides you.

[extra88]

How do you know you haven't had numerous emails marked as spam and never seen by the recipient? Do you receive a reply to every one you send?

BTW, AT&T's customer email is now hosted by Yahoo.

[jankins]

Certainty is difficult. I use the approach mentioned - I maintain email accounts at 3-4 different popular providers anyway. If I do ever notice something fishy I'll send to a couple of them.

Since I'm only using this for personal email, and that's at a lower volume vs. work email with different communication patterns, I think it's a little easier to detect failed sends (in other words, usually some response is expected, even if it's just "ha"/"cool"). But you're right, some might have been lost in the spam folder and never seen.

[jankins]

To clarify further:

Uncertainty is the cost of gaining more ownership, and I don't want to downplay that. If I'm sending messages where I want to maintain as much personal ownership as possible, I use my personal mailserver and accept the risks. If I'm sending mail where I need higher certainty and don't care about ownership, I use other providers.

Another commenter said: "if you absolutely depend on the ability to send emails such that your recipients reliably get them, hosting your own email server is extremely tricky." I agree with that -- different communication has different needs/requirements, and a self-hosted mailserver gives some benefits that I really like and that you can't get any other way. I'm just saying for me and for my common uses, it doesn't feel like a constant headache + battle.

[kuczmama]

You can try sending it to yourself from different email providers and check to see if it went to spam. For example I created a gmail and outlook account and sent emails to it from my hosted email server, once I had things set correctly I was able to validate the emails I was sending weren't going into spam.

[extra88]

How many different hosts are you going to create accounts on and send test emails to? Are you going to check the MX records for grandma's email to figure out who's hosting her email to test with that one?

Testing is not a one-time thing, the hosts keep changing their rules and if your ip is close to a spammer's that could change the treatment of your email as well. I sent email from my own domain address via an authenticated university SMTP server for years without hearing of any problems. Then this year, family members using Gmail started finding my messages in the spam folder. My best guess is Google started caring about the lack of an SPF record for the SMTP server, associating it with my domain but there's no way to know.

This is all way the advice for most people is: Don't run your own mail server, it's too much work and less reliable.