[ttul]

When it comes to email delivery, you can't ignore spam. It's the bane of existence of every email sending service and the number one business challenge in that segment. After all, orchestrating delivery over SMTP is not rocket science. But getting that email to not be rejected totally IS rocket science and it's simultaneously an art form known only to a handful of email nerds working at the core of the big email sending services...

[embedding-shape]

Ok, but what about as a CDN/website-proxy/WAF? I know we don't have the same automated reputation-propagation as with email, but same thing supposedly happens there, where eventually you get turned off if you don't act on lawful requests, which is exactly why Cloudflare is unavailable in Spain during La Liga matches, because Cloudflare don't take piracy streams down.

In theory, Cloudflare should take those down, when requested by legal means, but that doesn't matter. How sure are we that they'll act differently for email, instead of trying to get rid of the reputation system instead?

> getting that email to not be rejected totally IS rocket science and it's simultaneously an art form known only to a handful of email nerds working at the core of the big email sending services

It really isn't, you need a clean IP and a clean domain, send handful of emails and you're pretty much whitelisted on most services out there. Maybe you'd say I'm one of the handful, but I personally know more than a handful others who also run their own email services, just like me, and besides the usual hassle of running your own service, as long as you don't spam, your emails will arrive as usual.

[ttul]

I run an email sending service at scale (billions of messages per month, tens of millions of end users, thousands of customers). Most of our software development and operational effort revolves around abuse mitigation. That has been the case for 15 years. It's a cat-and-mouse game with two different mice: the senders, who are constantly trying to figure out how to get you to deliver their garbage; and the receivers, who are constantly trying to figure out how to block it. We're stuck in the middle.

It's hard to appreciate how difficult this battle is when running at scale.

[embedding-shape]

Right, I won't disagree with any of that, but I'm not sure how it's related to what I wrote either. Maybe I should have been more specific that I'm talking about hosting your own email, not hosting emails for others, which brings out a lot of other types of problems.

[ttul]

Apologies. When you said "email services" I thought you were implying "email services for use by others". Yeah, you can definitely run your own mail server in 2026 and I think the internet community should always strongly endorse being able to do so. Unfortunately, large email receivers have to make do with imperfect signals when making filtering decisions, and your traffic from a lonely IP that happens to have a bad neighbour might get blocked as collateral damage.

One long term hope: That domain name reputation eventually overtakes IP address reputation entirely.

[chrisandchris]

> billions of messages per month

Just tangential, but maybe that is part of the problem, isn't it? Napkin math tells me that esch person in the world receives every month an e-mail from you, and you're obviously just one of hundres of providers, and only half of the population actially has e-mail... I think you get the point.

E-Mail got to the point where it's actually worse then physical mail to some degree. Physical mail at least has a hurdle for the sender, and it's easier to throw away without even looking at it. The amount of low-quality mail and annoying, unnecessary notifications I receive is just at a level where I really think of dropping e-mail except for absolute becessary services.

[pbronez]

What structural changes could we make to improve the situation?

[ttul]

That is such a great question and there is no easy answer. There have been enormous efforts to do better for at least the last 20 years. An entire organization, M3AAWG, was founded for that reason and it meets three times a year, bringing together all the people that matter for making the situation better. It's a great organization and the people are all really smart and awesome. The IETF is no slouch either, coming up with excellent new standards and improving existing ones, such as the recent update to DKIM.

That's about as good of an answer as I can provide: keep sending smart people to the conferences!

[b112]

It's simple, there's a standard, a new one, which takes into account SPF, DKIM, DMARC, ARC, and even DANE along with upcoming and purposed SPKF, DKIM+, DMARC2, and ARCv4. It should fix just about everything.

[brightball]

Obligatory https://xkcd.com/927/

[jgalt212]

Hashcash, or BTC.

[ttul]

I always loved the hashcash concept and actually raised our original funding because of it (our Microsoft angels loved the idea of making spamming more expensive, and our Series A concept was tar-pitting to dissuade botnets). In the context of email sending services, we have a modern version of hashcash that we might at some point turn to. If someone can figure out how to tokenize sending at scale, then senders could pay recipients to open their emails by attaching a "tip" to each message.

If even a small fraction of legitimate email recipients altered their mail client settings to route "tipped" messages to their inbox, that would probably suffice to get senders to participate in the scheme. Senders are starved for high quality engagement data. Meanwhile, anything we can do to make spam less likely - on a relative scale - to reach the inbox in comparison to "legitimate" traffic, is a win.

[drumdance]

Wow, this brings back memories. Way back in the 2000 I worked on a concept to charge “postage“ to big senders and remit payments to receivers (hosts, not end users). I also looked at hashcash. I ultimately abandoned the project because I realized I would be spending all my time convincing big senders why they should pay and I knew I would hate that job.

Previously I was the spam cop for a big sender and saw up close all the ways our clients would try to weasel around it.

[edoceo]

Signed senders?

[i_think_so]

> I run an email sending service at scale (billions of messages per month, tens of millions of end users, thousands of customers).

Giving you the benefit of the doubt and accepting your claim, doesn't that make you one of the people at least second-order responsible for the current state of affairs in email blocking? It would seem that your company, by dint of your volume, navigates roadblocks that the rest of us (ie. the 99.999% of Internet email servers and their admins), who aren't FAANG et al[1], have to deal with to get our users' legitimate email delivered.

If so, could you perhaps give us a brief explanation as to why an otherwise competent engineer can "follow all the best practices" with their server which has no known compromises[2], on an IP address they have controlled for, oh, let's say a full calendar year, and yet still can't get off those FAANG et al default-deny blocklists, but you can?[3]

A cynic might say that your service had a vested interest in paying for unimpeded access to those FAANG et al companies to get over the bar that the rest of us are unable to vault. A cynic might also say that those biggest of the big email services like it that way, because it drives more users to them at the expense of the rest of us 99.999%.

I'll try to remain open to the possibility that there are aspects of the industry I've not yet had any exposure to, and refrain from chimping out over having my users blocked through no fault of their own.

[1] Yes, I know, Facebook doesn't receive anywhere near as much email as they send, and Hotmail = Microsoft, etc. If I used an accurate acronym I could pat myself on the back for being Technically Correct, while nobody would know what the heck I was talking about.

[2] We shan't digress into a discussion of hardware/firmware/OS/application backdoors nor Snowden disclosures. It's not that hard to auto-install security updates and run a reasonably tight ship with no unnecessary attack surfaces.

[3] Or perhaps there aren't any default-deny blocklists at all, but in fact only much smaller default-allow whitelists? That would be cynical indeed.

[pocksuppet]

Cloudflare acts on lawful requests during LaLiga matches. The problem is that the Spanish government doesn't want to bother doing things the lawful way because that takes too long. They want piracy to magically disappear and they'll randomly shut down more parts of the internet until it does. Actual illegal sports streams are not impacted by Cloudflare being down, and Cloudflare is not the only impacted network.

[embedding-shape]

> problem is that the Spanish government doesn't want to bother doing things the lawful way because that takes too long

In Spain, what they are doing, is the "lawful way", it's literally happening via the courts and judges. Do you think ISPs are blocking Cloudflare specifically just for fun, out of their own accord?

> Actual illegal sports streams are not impacted by Cloudflare being down, and Cloudflare is not the only impacted network.

Some are, many aren't. Cloudflare is indeed the only impacted network, at least for me. Which other networks are being blocked for you during the La Liga matches?

[Dylan16807]

The specific blocks don't go through courts and judges.

[embedding-shape]

Yes, the specific block of blocking Cloudflare in Spain during La Liga matches literally has gone through a court and been ordered by a judge, I'm not sure how you could have missed this. Judges have also dismissed the requests from Cloudflare and others to remove the "dynamic block" as there is collateral damage.

[Dylan16807]

My understanding was that cloudflare was being blocked by the same IP blocking list as everything else. And while that system went through courts, the list didn't.

There are also direct actions against cloudflare, but that's not what's taking everything down, is it?

Did I misunderstand something?