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Re:The “mail is hard” myth by akerl_ on Sunday September 01, 2019 @09:54AM (#20852266)
The article handwaves this by pointing out that it’s “proof-of-work”. Which is a fancy way of saying “it requires a bunch of work, continuously as the rules change over time”.

Which is why I’d consider it “hard” to run my own mail server. The complexity of running a daemon with a config file isn’t the issue, nor is it that any individual task of SPF/DKIM/etc is complex. It’s that I generally want to put 0% of my time into making sure my emails are being received, and I’m receiving other peoples’ emails.

Re:The “mail is hard” myth by jdboyd on Sunday September 01, 2019 @11:57AM (#20852922)
In my experience of over 15 years, the "rules" have only changed 3 times since I started. First to require good reverse DNS, then to require SPF, last to require DKIM. The transition on each of those was generally several years with plenty of publicity.
Re:The “mail is hard” myth by bt848 on Sunday September 01, 2019 @12:53PM (#20853255)
That hardly covers it. The problem is that who "you" are, your identity as a sender, is not entirely within your control. The big mail operators figure in a ton of stuff, like the reputation of your subnet - /24 maybe, or /96, it's an approximation - or the reputation of your AS, your domain registrar, all kinds of stuff. If the guy on the next IP over is sending spam that's going to pollute your reputation.

If you have your own ASN and your information is registered with reputable parties in lawful countries, you might not have much to worry about. If you are using a cheap cloud VPS service whose network is registered to a Romanian holding company, nobody will deliver your mail.

Re:The “mail is hard” myth by toomim on Sunday September 01, 2019 @01:13PM (#20853371)
You're forgetting DMARC.
Re:The “mail is hard” myth by teddyh on Sunday September 01, 2019 @01:56PM (#20853632)
If you already have SPF and/or DKIM, adding DMARC is a matter of setting one static DNS record and never changing it again. Hardly difficult.
Re:The “mail is hard” myth by scarejunba on Sunday September 01, 2019 @02:30PM (#20853844)
I don’t have DMARC setup and can still send to Gmail.
Re:The “mail is hard” myth by brianpgordon on Sunday September 01, 2019 @10:39AM (#20852513)
It would be nice if these big mail services accepted actual proof of work as a way to guarantee that your mail gets through. Maybe someone could extend SMTP with a bitcoin-like challenge where the server sends the client a nonce and a difficulty factor, and the client has to reply with a suffix that you can append to the nonce so that the whole string hashes to something with the corresponding number of zeroes at the end. People sending personal emails will be happy to burn a penny of CPU time as "postage" but spammers won't be able to send their spam profitably, especially if you increase the difficulty factor based on how many emails you've sent in the last hour.
Re:The “mail is hard” myth by jcranmer on Sunday September 01, 2019 @11:02AM (#20852636)
> People sending personal emails will be happy to burn a penny of CPU time as "postage" but spammers won't be able to send their spam profitably

The problem with this idea is that spammers don't use their own computer, they borrow other people's computers to send the spam. It also heavily penalizes people who legitimately need to send bulk email.

Re:The “mail is hard” myth by Nullabillity on Sunday September 01, 2019 @11:51AM (#20852892)
> It also heavily penalizes people who legitimately need to send bulk email.

Aka spammers.

Re:The “mail is hard” myth by dasil003 on Sunday September 01, 2019 @12:33PM (#20853143)
Believe it or not there are email newsletters and mailing lists that people legitimately want to receive.
Re:The “mail is hard” myth by jcranmer on Sunday September 01, 2019 @12:36PM (#20853156)
Such as the Linux kernel mailing list.
Re:The “mail is hard” myth by amelius on Sunday September 01, 2019 @12:41PM (#20853179)
Yeah, but for bulk-mail one could introduce "whitelists".
Re:The “mail is hard” myth by hakfoo on Monday September 02, 2019 @10:25PM (#20863261)
One of the big corner cases I've noticed is transaction-oriented email-- the password resets, "welcome to your account" emails, order details, shipping notifications. People want these, but they're probably harder to deliver than personal email or much spammier bulk mail sent directly via outsourced experts.

These have a lot of iffy issues.

* Since they're going to be generated by the ecommerce service, it may not be running on the same server or IP block as your main mail infrastructure, so you might have to specially configure around that.

* The content-- hundreds of messages a day, at seemingly scattershot recipients and highly templated-- screams spammy nto the wrong algorithm.

Yeah, there's services like Mandrill, but the whole ecosystem feels broken. It's not serving mailers. It's not serving the recipients very well. It seems designed to please a small, delicate, vocal audience. The people so upset at the prospect of false negatives (spam in the inbox) that they rally around providers who are prone to aggressive false positives. Who are these people and what makes them tick?

I could see this backlash in a situation where it's high risk or cost, but users can manage their own filters in any half-decent mail system, and frankly, clicking through a few pieces of spam a week is not a big deal-- arguably far less a hassle than spending an hour on the phone to get a tracking number that a spam filer ate.

Re:The “mail is hard” myth by zbentley on Sunday September 01, 2019 @03:30PM (#20854247)
(Note: deleted and moved here because I put it in reply to the wrong comment)

I work for an email marketing provider (opinions my own, obviously), and I was extremely surprised how many people genuinely want to receive lots of commercial bulk marketing email. And by "want to" I don't mean "don't mark as spam", I mean "continually sign up for different marketing newsletters, and consistently use links in newsletters/marketing emails to make purchases from multiple companies". It's an alien phenomenon to me, and it may be a minority of bulk email, but it definitely is useful to a lot of people. Maybe it's their equivalent of coupon-clipping-based shopping, or maybe they just like learning about things to buy in that format? I have no idea.

That aside, the last thing an email marketing platform wants to do is send spam. Every time someone marks an email such a provider sends as spam, the reputation of their sending addresses is damaged, and therefore their ability to deliver mail to aforementioned people who want to receive them (and therefore the ability of the marketing platform to make money by facilitating that kind of desired email) is jeopardized.

TL;dr there's bulk marketing email and then there's spam, and surprisingly little overlap (and overlapping incentives) between the people who send each.

Re:The “mail is hard” myth by boring_twenties on Sunday September 01, 2019 @06:28PM (#20855433)
Sure, I do this. A lot of stuff people buy is often a lot cheaper with promotions. Just the other day, I bought a $600 set of tires for $300-380 (depending on whether or not I remember to do the mail in rebate). That alone is well worth the few clicks it took to filter mails from that list out of my inbox and into a label for car-related marketing.

I have a couple of broad categories for these filters like car stuff, computer stuff, other-hobby-related-stuff and of course clothing, and just take a look at the appropriate one when I need or want something. Takes virtually no time, and saves a lot of money.

Of course I'm not gonna lie, I do end up buying things that I wouldn't have bought otherwise by doing this. But some of those things are pretty cool, too. :) I do have a few more cheap ARM boards of various types than I can probably use, though.

Re:The “mail is hard” myth by esotericn on Sunday September 01, 2019 @10:47AM (#20852545)
https://en.wikipedia.org/wiki/Hashcash

> Hashcash was proposed in 1997 by Adam Back[1] and described more formally in Back's paper "Hashcash - A Denial of Service Counter-Measure".[2]

Re:The “mail is hard” myth by brianpgordon on Sunday September 01, 2019 @11:09AM (#20852677)
I guess the idea was too obvious to be original. I'm surprised that it inspired Bitcoin instead of the other way around though.
Re:The “mail is hard” myth by fanf2 on Sunday September 01, 2019 @11:16AM (#20852709)
Proof of work proves not to work (2004)

http://www.cl.cam.ac.uk/~rnc1/proofwork.pdf

Re:The “mail is hard” myth by brianpgordon on Sunday September 01, 2019 @11:58AM (#20852927)
The paper's argument assumes that the PoW scheme is required though. It could be an option which just guarantees that individual mail can get through, while still keeping the usual reputation-based spam filtering for clients which don't want to participate.
Re:The “mail is hard” myth by jcranmer on Sunday September 01, 2019 @12:40PM (#20853177)
If there's one lesson from the history of spamming, it's that spammers are among the fastest adopters of anti-spam technologies. If PoW meant that spammers could only send 1/100th the email, but the email was 1000× more likely to actually show up in an inbox, spammers would jump on it in a heartbeat.
Re:The “mail is hard” myth by brianpgordon on Sunday September 01, 2019 @01:38PM (#20853494)
That doesn't make sense. Each email is only worth so much to a spammer. They can't lose money on every email and make up for it with volume.
Re:The “mail is hard” myth by jcranmer on Sunday September 01, 2019 @01:53PM (#20853608)
The value to spammers isn't in email delivered, it's the actual user engagement at the end of the process. A million messages delivered to the inbox is worth far more than a billion messages delivered to the spam folder.
Re:The “mail is hard” myth by hakfoo on Monday September 02, 2019 @10:40PM (#20863332)
A million messages delivered to the right inboxes are valuable.

The quantity-above-quality model in the spam industry probably lead to low-quality or vague list criteria. Broad demographic groups and domains. A lot of third party data of questionable legitimacy. If you've been running the list a long time, some "email address [email protected] clicked on campaigns A and B" data. You might be able to say on a large scale "List A is likely to convert better than B", but it still comes down to spray-and-pray at the individual address level.

If you went to a spammer with a few "sucker lists" of 100k emails each, and told him "you can only send 1k per day", will he have the data to triage his list to get a decent return on it anymore?

This would also snowball over time. Without being able to do high-volume campaigns initially, they'd have a harder time building up the knowledge they can use to manage their lists, and the quality would decline over time.

Re:The “mail is hard” myth by scarejunba on Sunday September 01, 2019 @02:27PM (#20853827)
Yeah, but if the marginal cost of the next message is higher than the marginal expected increase in revenue then they won’t. It doesn’t matter optimizing inbox delivery rates if per-delivery you lose money.
Re:The “mail is hard” myth by brianpgordon on Sunday September 01, 2019 @02:59PM (#20854034)
Keep increasing the PoW cost and think about where that line of argument leads you. "One message delivered to the inbox is worth far more than a billion messages delivered to the spam folder." One single delivered message is going to be profitable for the spammer? Clearly not. This proves the existence of some break-even point at a lower cost. Mail providers just need to set the cost above this point.
Re:The “mail is hard” myth by jcranmer on Sunday September 01, 2019 @03:16PM (#20854149)
Given that spammers mostly use others' computers to blast their email out, I suspect that the price point that would truly throttle spam would be higher than the price legitimate users of email would be willing to pay. I'm not sufficiently knowledgeable in spam and black market economics to throw any actual numbers around.
Re:The “mail is hard” myth by amelius on Sunday September 01, 2019 @12:45PM (#20853198)
Also, they didn't consider that slow machines can still provide proof of work by relaying it to a fast machine (perhaps in exchange for real money).
Re:The “mail is hard” myth by prirun on Monday September 02, 2019 @12:04PM (#20859909)
It's an interesting idea, but wouldn't this be easy to abuse though, like Gmail could force Fastmail to do huge proofs of work before accepting their mail?
Re:The “mail is hard” myth by amelius on Sunday September 01, 2019 @12:36PM (#20853157)
> Which is a fancy way of saying “it requires a bunch of work, continuously as the rules change over time”.

Wouldn't this be a good task for an open-source package to handle? If you'd just updated the package regularly, your mail would always be sent according to the rules. No need for any third-party handling your mail.

Re:The “mail is hard” myth by jasode on Sunday September 01, 2019 @02:16PM (#20853749)
>Wouldn't this be a good task for an open-source package to handle? If you'd just updated the package regularly, your mail would always be sent according to the rules.

Some of the "rules" for reliable outgoing email delivery cannot be encoded inside the source code files of a github repo, or email setup bash script, or a Docker image, or a EC2 virtual image, etc.

An example of an unspecified "rule" outside the boundaries of a local machine holding the email server is recovering from an unexpected blacklisting of ip addresses. Example.[1] A preconfigured Docker image of Dovecot isn't going to magically ask Amazon support staff why the ip address is blacklisted and/or move the server to a different ISP etc. If a bad actor (that you are unaware of and have no control over) happens to share your ip address block and sends out spam which then causes Gmail/Hotmail/Yahoo to reject your server's emails, there's no open-source programming code that can detect and fix those problems happening outside of your control.

Or put another way, if HonestJoeBlow could download a constantly updated Docker image that has the so-called "correct rules" for sent emails to always be accepted by Gmail, it would mean the DishonestSpammers could also download that same Docker image to get their emails delivered.

The issue is that "trust" in the email ecosystem is an emergent property among participants and therefore, it can't all be embedded inside email server configs, or in a DIY blog article trying to explain the exact 12 steps to make email delivery work perfectly with all receivers. Eventually, something can break (because a receiver changes their idea of "trust" and "spam") and it requires troubleshooting & debugging to get email delivery working again.

A tldr would be: You can't put "sender reputation" into a downloadable software package.

[1] https://forums.aws.amazon.com/message.jspa?messageID=724690

Re:The “mail is hard” myth by Ayesh on Sunday September 01, 2019 @09:50PM (#20856216)
This would allow spammers to evade the rules all the same. For anything that is standardized or agreed upon, we can of course have packages like this. Time zone data (tzdata), IP Geolocation databases, etc.