I wish there were a way to self-host without my emails constantly getting stuck in other people's spam folders. And it made me really paranoid about email, too -- like I'd send emails, and I'd never know if the other end received them or not, unless they replied. Without a reply, I would always wonder whether the message got a look, or disappeared without a trace.

The only way around this seems to be hosting with Google, Microsoft, or maybe Proton. Any other ideas?

I ended up switching to Fastmail a few years ago, but before that I was relaying outgoing email through Amazon SES. It fixed all my deliverability problems. Before that, when sending from my own server, emails might just not show up. Not in recipient's spam folder, not rejected by their server. Accepted and then dropped mysteriously.

If I ever go back to self-hosting email, I would do the same except I would maintain a whitelist of friendly mail servers to which I would send directly. Or maybe just relay emails to Google/Microsoft via SES and send the rest directly.

It feels like the only way to stop this happening reliably, is to get as many people as possible off Google and Microsoft.

I'd argue that self-hosting is the first step. The second step is helping everyone you know get their own domain and host their email for them. If they don't trust you to not read their email on your server, point them to somebody else who offers mail hosting.

The more people we can convince the internet is something anyone can help build outside of the silos, the more likely it is to survive.

One way to tell whether an email has been opened or not is to include a 1x1 transparent pixel that is hosted on a server you control. If the email client the recipient is using automatically loads images, you will get a hit to your webserver for the transparent pixel. This only works if display of images is enabled, so it's not 100% reliable. Some email clients turn off automatic loading of any external content by default for privacy, but it still has value and will help you track opens.

Also, set up seed accounts on different email providers and subscribe them to all of your lists, this helps you get an idea for what other people are seeing when they get the emails. If it's going to a seed account at gmail, and getting sent to the spam folder, you can try tweaking the email and work around the issue with some A/B testing.

Use DKIM on a long lived domain, and check that your sending IP is stable and comes from a block with good reputation. This has always worked for me.

Ran into this issue when self-hosting, so I just bumped my existing ProtonMail subscription to a business one which allows for mail forwarding. It's quite easy to set up and I've been pretty happy about deliverability for a year+ now

I haven’t had this issue. It might be due to the long-standing reputation of my email domain(s) or of the mail server’s IP address, I don’t know. But I know other self-hosters who don’t have that issue either.

I use fastmail which is very good. Like “oh this is how it should feel!” good.

I started self-hosting my email last year, but I use MailPace (other email sending services are available) to avoid being memory-holed.

I don’t self host, I pay zoho to do it. Over never had any suspicion my emails haven’t been received.

I think that is the Crux of the issue.

Email spam has made self hosting untenable.