- Setup blacklist monitoring (e.g. HetrixTools/MXToolbox)

- Check if you can email Gmail

- Check if you can email Hotmail

- Check if you can email Office365

- Check on Microsoft SNDS that you are not blocked: https://sendersupport.olc.protection.outlook.com/snds/

Gmail, Hotmail and Office365 are the largest email providers and also the most strict ones.

I have accounts on all of these providers so testing deliverability is trivial. You could argue that testing deliverability with one account is unreliable but in my experience it simply is not. Usually you send a couple emails across a week and if they all go through you are good.

If you are paranoid, you can ask if any of your friends have Office365/Hotmail and email them. They probably have company or university accounts on there.

My server has only been blocked once after all this, and ironically it was by another company that self-hosts their email...

No, it's not trivial, and no, it doesn't work like that. It's fairly easy to get a test email to your own gmail/hotmail/office365 account delivered. It doesn't mean your other emails get delivered.

For example, when I needed to send out a link for my wedding photographs to my wedding guests, I did exactly what you suggested: I sent a few test emails to Gmail and Hotmail test accounts that I had set up, confirmed that they delivered, and then proceeded to send the actual email which had a link and like 50 people in the BCC field. Guess what happened: all the Gmail accounts placed my email in the spam folder. So then I had to later send another email, using a different email provider, asking people to check their spam boxes for the link (this time not including the link in the body of the email with the hope that it would increase the chances of delivery).

Note that this particular anecdote is not of self hosting email, it was using Migadu (I was initially not trusting that they can deliver email properly, so I ran those tests like you suggested, concluded that they seem to be delivering email, and then my actual real email was not delivered).

Actually I initially got placed in spam too in Gmail/Outlook but I always replied to my own emails and marked them as "Not Spam" and the problem just kinda disappeared?

When I initially setup my server I was paranoid (as you should be) and so I had the following protocol:

- Send all urgent email with Gmail

- Send non-urgent email with my own server. If I don't get a reply within 24h, send again with Gmail, explaining my email troubles. Usually the other party would happily confirm whether or not my email landed in their spam without me even asking.

It was never a cold-turkey migration to my self-hosted setup. It was more of a slow process over a couple months after I gained more and more trust in my server.

Did you continue to use those same Gmail/Outlook accounts for your deliverability testing? Because that would explain why you're not encountering any deliverability issues in your testing.

Try to create fresh Gmail and Outlook accounts and see if you can actually deliver to them.

I had a couple Hotmail/Microsoft Live/Outlook accounts too.

But deliverability for me was always quite consistent. If it went to spam on one account, it would go to spam on all of them.

At this point I no longer do deliverability testing because I simply don't see the need to. No one has ever complained about my emails going to spam so the thought has never really crossed my mind.

I've also had a lot of trouble creating Outlook accounts for some reason. New accounts seem to get suspended real quick. My previous Outlook accounts have mostly all been suspended too. Not sure what's going on there...

EDIT: From the output of `dig` I can see my landlord uses Outlook. I just emailed him a couple days ago and he replied so I guess all is well?

You mentioned that your emails on Gmail and Outlook initially went to spam, but that you clicked "not spam" on those emails. This action should prevent your emails being flagged as spam for that particular receiver who clicked not spam. Obviously it can't work such that one person clicks "not spam" on an email, and then everything from that sender is whitelisted for everybody. Because then the spammers could just register a single email account, click "not spam" once, and then spam everybody. So my point is, if you test deliverability on email accounts where you have already whitelisted the sender, of course it's going to look like email is delivered.

> I just emailed him a couple days ago and he replied so I guess all is well?

Presumably you and your landlord have already emailed each other in the past, so any anti spam system should allow emails between those addresses to reach their destinations. It doesn't really prove anything.

Obviously I'm aware that me clicking "Not Spam" would not instantly whitelist me in Microsoft's systems, but the hope is that it would influence the spam algorithm somewhat. It doesn't even whitelist me on that account because even after clicking "Not Spam", my emails still went to spam for some time.

> Presumably you and your landlord have already emailed each other in the past, so any anti spam system should allow emails between those addresses to reach their destinations.

Maybe, but my entire university runs on Office365 and I never had any trouble sending to friends and professors there (who have never sent me emails previously).

I'm not really sure what you are trying to say here? Should I have some sort of commercial deliverability monitoring system setup? Do you have insights into what "real email providers" use?

Or, if I were to put a larger point behind it, I would say that getting good deliverability is hard and it doesn't make sense to try it unless you are delivering email on behalf of a large amount of people (rather than merely yourself).

We read from different cookbooks and my reading comprehension is high. My sent email stats shows over 20K successfully sent emails just for my personal account, since 1999, when I started tracking it.

Ok, since you claim to have measurements, let's hear what they are:

- What is the total number of emails sent?

- What is the number of emails bounced?

- What is the number of emails that landed in inbox (as opposed to spam)?

- What is the number of emails blackholed? (recipient confirms delivery, but email doesn't show anywhere, not even in spam folder)

I feel like for every pro host-your-own-mail on HN there is one that contradicts it.

After many hours of this over many months, I finally looked for a comparison of the actual taste of coffee from cheap grinders versus 10-20x more expensive burr grinders. (As opposed to comparisons of grinder technologies, which are everywhere.)

There are almost no published side-by-side taste comparisons; when I did find one, the cheap grinders had won!

I can imagine, because why would taste matter for a coffee /s ?

Setting up a server is trivial, yes. Keeping it going is a never-ending treadmill of not really technical problems.

I can't see the future, if the big email providers who likely have some of their trolls posting in the comments ever decide to start choking out us personal email server runners, then it'd be game over. If things remain for the next 20 years assuming I live that long then deliverability would be 100% for the next 20 years.

> Do you know some magic incantation for staying off the naughty lists?

I don't spam, that and don't make a finger fumble edit like I did the one time in over 20 years and didn't check to make sure it was working correctly first.

Also, I use http://www.mxtoolbox.com/ to keep an eye on my server.

Not magic, but when I managed outgoing Postfix servers for a few companies I had to set rate limits for yahoo.com an a couple other domains to reduce concurrency or they would block one of the SNAT's for a while. It probably sounds tedious but it really wasn't. There were not many MX that were as strict as Yahoo. I never ran into issues with Gmail but I think they cut some slack for corporate IP addresses and domain names.

For my own personal email servers I never had issues because I never sent at a rate that anyone cared about. The closest I got to that was running a forum that would email when threads would get updated and people subscribed to them but my solution there was to suggest to the people on the forum not to do that.