[baobabKoodaa]

> 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.

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).

[nulld3v]

I guess I simply cannot share your pain because I've never had these problems.

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.

[baobabKoodaa]

> 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?

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.

[nulld3v]

I have multiple Gmail accounts (like 5+ lol) as well as my own Google Workspace account (for unlimited GDrive) so for deliverability to Gmail testing I just used that.

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?

[baobabKoodaa]

> 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.

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.

[nulld3v]

> 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.

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?

[baobabKoodaa]

I guess I'm mainly trying to point out how difficult it is to estimate deliverability. So, rather than pointing to a solution, I'm merely trying to illustrate that the problem exists. There's so many people in this thread claiming that measuring deliverability is "trivial" or getting deliverability is easy ("just do X,Y, and Z"). And when you get down to it, it's mostly people saying "I sent an email to myself and it went through" or saying "nobody ever emailed me back saying they didn't get my email", and so I'm poking holes at those anecdotes. No larger point behind any of this.

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).