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by qurren 23 days ago
Aw hell. How many things do I have to set up just so that I can send e-mails from my own domain?

The effect of all this seems to be less "making e-mail secure" and more "making it so that only Google, Apple, and Microsoft can send e-mail successfully"

6 comments

DKIM2 and DMARCbis are actually the opposite of this. They are long awaited fixes of brittle and often broken systems that are designed to now make providing secure email easier rather than harder.

They both have fairly clean migration paths and resolve a lot of the annoying edge cases that currently exist with authenticating and verifying email.

Thanks for this, it made me actually read the posted content, but there's a lot of content to digest and a lot MTAs will have to implement.
And sometimes if you do everything right, it still doesn’t work.

Recently I checked the IP against blacklists, waited a few months, did all of the other things, and then found out Microsoft bounces my entire VPS’s IP range. Appealing did not help.

They intermittently block Cloudflare email routing IPs too. All of these security measures and still it comes down to the IP address of your sender.

Is it an el cheapo VPS?
Is Cloudflare a cheapo VPS?

It is a cheap VPS, but it would still be nice if there was a way to know (not assume) beforehand.

> 550 5.7.1 Unfortunately, messages from [IP ADDRESS] weren't sent. Please contact your Internet service provider since part of their network is on our block list (S3150).

> Your IP(s) qualify for conditional mitigation.

Still blocked. The system is working as expected.

Cloudflare is one of the shadiest hosts around, almost as bad as the big three clouds.
You can't have the cake and eat it too.

Either you use cheap infrastructure that attackers can buy by the bulk for sybil attacks.

Or you pay a reasonable price for a slice of an IP block that doesn't share its reputation with elcheapos.

No disagreement here. I had never planned to use it for email, but I was bored and I already had it when I got an idea.
I would simply like to point out that 550 at SMTP time is not a bounce.
You get an email bounce back with an error code in it. Is there some other definition I'm unaware of?

Wait, that is probably from the local mailer, and otherwise the sender may never know about the rejected messages.

5xx are bounces, a perm failure. 4xx error codes are temp (retry) errors.
Incorrect. A bounce is a delivery status notification generated by a mailer after it has already accepted a message for delivery. A 5xx permanent error is a refusal to accept the message in the first place.
DMARC isn't for sending email successfully, it's for preventing other people from impersonating your domain. Without it, there's nothing stopping anybody from sending an email saying it is from you@qurren.com. SPF tried. DKIM tried. Both of them had gaps.

When you use them together and have a DMARC policy that requires one of them or the other for successful delivery, it's the best current solution.

Right, and when you don't configure DMARC successfully and the recipient requires DMARC, then you cannot send email successfully.
Yeah. And when you don't configure your TLS certificate correctly, people can't connect to your webpage.

The anti-email authenticity standards gang has always smelled like the anti-TLS gang to me.

That's a feature, not a problem.
Except I think I've had 1:1 personal e-mails from my domain go into a legitimate recipient's spam filter just because I didn't have DMARC set up and their mail server was flagging that "DMARC not set up == spammy domain"
That is perfectly reasonable. Set it up correctly.
It is so much easier to set these things up with a frontier AI to walk you through the Byzantine steps.
It takes an afternoon to set up DKIM and DMARC from scratch on a debian VPS. Yeah it's a little bit byzantine but it's not rocket science.
Yeah I did that. Now it seems I have to set up DKIM2 and DMARC2 and DCRAP3 and DSHIT4 for another afternoon instead of just going to work and getting shit done.
Too many admins just had it set to “no valid DMARC? Spam” instead of the more proper “failed DMARC? spam”.

Which is subtly different.

This sort of Regulatory Capture is quite old in the software field. People were already noticing it in the 90's.

Making a spec that contains a venn diagram of most of the features each of the signatories to the specification have implemented themselves ends up pulling the ladder up behind them. Each non-academic committee member discovers they're already more than 75% of the way to having completed the spec and any junior members or amateurs have years of work to do in order to catch up to Now. If any upstarts threaten to get within striking distance of an implementation you can always convene the committee again and discuss version 2 of the spec.

Mobile devices tamped this down just a little bit but mostly they lowered the slope of the line a hair and changed where the focus was a bit.

> Aw hell. How many things do I have to set up just so that I can send e-mails from my own domain?

... said every spammer.

I'm sorry for your pain, and I'm in the same boat.

But it's important to understand that any sufficiently large, distributed-agent system (like federated email), will see the rise of parasites that will pump resources and diminish the value of the system.

What we're seeing here is an "immune" response to those parasites. We all pay for it.

I think this is an important lesson for anyone designing a distributed-agent system [1]. How do you design it so as to keep the bad actors out, or at least so their impact is negligeable?

[1] imma make my own email system! With blackjack, and hookers! oh wait...

>>parasites that will pump resources and diminish the value of the system.

Countries' legal systems really need to do something about them.

I don’t think they can. Spam, like speeding on highways and drug sales, is such an asymmetric enforcement area that I have very limited confidence that legal enforcement would make a significant dent in the volume. It’s far too technically easy to anonymously, repeatedly break anti-spam laws. This is an area where consortium enforcement (like the big inbox providers pushing solutions like DKIM2) is probably the most effective.

Don’t get me wrong, there are tons of areas where countries’ legal systems have no excuse for not enforcing the law more stringently (e.g. flagrant corruption in multiple regulatory bodies’ failure to enforce investment/wire fraud). But spam is part of the other category—technically difficult enough to crack down on that legal action is a waste of time. There are ways to change that, but they’re all either more centralization-prone, worse for privacy/liberty, or extremely expensive.

They keep finding that huge spam campaigns were run by one guy from his bedroom. I can't remember which specific spam campaign was recently caught, it might've been the phone spam about car insurance. It was one guy with a huge botnet.

In total they are a finite set, and even catching 5% of them will scare the rest.

I interpret that the opposite way: if a huge spam campaign can be run by a guy in his bedroom, there’s no way that larger spam operators can be effectively killed by legal action. They’ll just employ different guys in different bedrooms. The same thing is true with phone phishing scams—they’re not individually hard to eradicate, but the combination of lucrativeness and rapid-rebootability means that legal crackdowns in the past have not been effective at scaring the rest out of business.
Did you know you can stay out of jail if you tell the police who's paying you?
I think about software engineering as virtual construction.

In the physical world, we can have police that go after criminals who break down doors. But builders also have a responsibility to install locks.

And negligently failing to build a lock is actually not a great look if you want police to give you the time of day.

Eh, I read the article, and at most you only have to wait for your MTA to update to add the required headers and update your DNS records and you are golden. It still uses the same key you generated as far I'm aware.