I haven’t productionized this setup (I send maybe a dozen emails a year) but it worked for me ad hoc a couple years back, when I had to send a mail to an Outlook-hosted address and they blackholed everything I tried to send while 250 OKing me.
It's always people self-hosting mail on a shared server in Moldova (because they think it makes them cool) that are complaining.
Which with cheap models like Jev as spam classifiers, this can now become a reality.
The problem is, Google and Microsoft have monopolized the entire email market, so their esoteric deliverability mysticism from 2007 still persists (basically blanket bans on entire IP spaces, locking out anybody trying to send emails on their own).
Email naturally followed this evolution.
https://www.mimar.rs/blog/a-journey-of-my-mx-server-to-new-r...
And yes, it's cool not to have to let scum read your private communications :D
It turns out that whoever has the most power is the most powerful. This is why distributed/decentralized systems cannot singlehandedly free us from tyranny, and why I find people who spend all their time preaching decentralized systems to be quite silly. We don't need better systems (well maybe we do but,,,), we need better education and awareness of how billionaires manipulate us; this goes beyond software.
Mail, then emails, then home phones, then cell phones, then texts, then social media have been gradually rendered less and less usable by bad actors systematically abusing every single tool we try to use to communicate with one another to steal from us, lie to us, and manipulate our beliefs, and we'll just keep inventing and discarding new ways of communicating until we reckon with this.
The only question is how many years the lazy network-effects monopolies (like Google, Microsoft, Verizon, etc) will hold this back from happening.
The optimist in me says this will unlock pathways to true decentralization of push communication protocols (like SMTP) instead of only have decentralization of pull-oriented protocols (like HTTP).
Selfhosted email is likely easier now than it ever was before.
Experience shows that the walls will get taller and the moats will get deeper.
The solution is allow only communications that are demonstrably not spam and not unwanted.
There have been lots of proposals to this effect but maybe you have to put up two cents in a crypto wallet, which the other person can claim if the mail is unwanted. If someone takes your two cents, you remove them from your lists ASAP. The receiver doesn't benefit meaningfully from the 2c so they are unlikely to claim it. The sender is only damaged if a lot of different people claim the 2 cents. Maybe a few domains are default whitelisted even if they don't put up 2 cents, to protect against entities that are important but would be frequently spite-claimed (IRS, courts, and other similar). If you use a provider that doesn't whitelist, fine, but you're going to miss those emails.
Maybe the top 'spite claim' users are published and it becomes difficult to get people to agree to put up money to talk to you.
This reduces spam to the level of junk mail, which is still not totally trivial but is orders of magnitude more manageable.
Seems they are the disease not the cure
It seems insane that gmail doesnt provide a way to automatically send a mail (eg based on domain, keywords, etc) to spam. I know theres block sender but for example aliexpress uses a different name for every email so that's useless.
What this is called is survivorship bias. The question I would ask is how much mail are you not seeing at all because it's dropped at the edge first thing because it's IP block listed?
Next, how much spam are you seeing from them because they and Google are the largest providers on Earth? Kind of like selecting a random person from the population in the US and going "look, it's a white guy". Yea, that's how statistics works.
Lastly, because the are good at blocking spam at the edge, then that's the last bastion of attack for spammers to put their efforts in if they want any return at all.
These entities communicate via plain old mail, that costs more than 2 cents already.
The people working on outlook.com are just talentless amateurs - the rest knows how to do it right. It's a shame it's so widely used.
Most of them wouldn't even care probably...
User signs up, uses @outlook. Your app declines it and explains that they block with no way to remedy, and explain they are a bad vendor.
Emails would be accepted by Outlook.com, but would never deliver. We had SPF/DKIM/DMARC and full reporting. They RBL'ed us with no remedy.
We told the customer to not use outlook.com BECAUSE we told them we could not guarantee any delivery of messages.
At the most you need to use an external service for delivery (usually because you have problems with MS) but you can still run your own server with no difficulties once you do that.
That said, DMARC is required by a lot of people now, so I do not think this particular issue is a problem.
I have been self hosting my my personal email (and for family). Few problems so far other than delivery to MS and I have recently moved a domain I use for work email over.
Oddly enough the MS problems come from hotmail, but not other services. If that is a problem, then pay a bit to have email delivered.
Fortunate for those running their own servers is that they actually still get all the cool emails from people not complying.
This is not Microsoft's fault. The building's on fire and they're locking out the arsonists.
I was working for Microsoft when outlook.com launched and got a good email address that was my primary for more than a decade.
I had so many issues with things getting silently dropped with no recourse (2FA codes, account recovery mails, etc.) on so many sites that I finally gave up, reversed the stream, and had Outlook forward to GMail instead of vice versa. A few months after that, I realized that all my Outlook got was an enormous volume (hundreds of day) a spam and that all legitimate mail was going to my other accounts, so I turned it off entirely and haven't read that mailbox in over a year.
This is not unique to Microsoft and really the source's problem — they did something to get blocked in the first place.
Add in the fact that you're almost certainly not the only one impacted, and that they have no interest in fixing it, it screams incompetence on the source's part.
Been there, done that, good luck explaining the problem to the app's first-level support in the Philippines because it's not in their script.
> and had Outlook forward to GMail
Till the day GMail hits you with the "We couldn't verify it's you" bullshit and locks you out of your account forever. Good luck getting support from Google, the word is not in their lexicon.
I've never encountered this issue with GMail. Delivery just works. I'm trying to think of the last false-positive spam flag I've had with GMail, and I've definitely never had mail be entirely dropped.