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The “mail is hard” myth

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Re: The “mail is hard” myth

#71

Post by Kaveren »

acidburnNSA wrote: post #37
number6 wrote: post #35

Earlier quoted context omitted.

Running my own for about 2 years now. Spf dMarc and dkim set it is accepted by all mail providers. I also get daily reports from Google how well it behaves

Same here, except to Charter, who has apparently just blacklisted swaths of DigitalOcean IPs, probably for some reason. So I just can't email my mom. Other than that, a great experience.

Are you using IPv6 or IPv4 to send the emails? DigitalOcean apparently blocks port 25 outbound IPv6 access because whole ranges are getting blocked.

Re: The “mail is hard” myth

#72

Post by xrisk »

rpcwork wrote: post #68

Managed mail server clusters for years with an ISP. Agreed, too many things that can break and cause PITA. However, ‘Hard’ is a subjective term. The deeper you are in a trade or the longer you have done it, the easier it comes to feel. I visited a family farm and found it very very hard to squeeze milk outta buffalo. My great uncle however has dealt with that buffalo that for years and didn’t sweat it one bit. In a s…

This is a great analogy. Why do more work when you can get the same result with less effort?

Re: The “mail is hard” myth

#73

Post by danShumway »

xienze wrote: post #62
swiley wrote: post #23

Earlier quoted context omitted.

I run my own mail server and as long as you use TLS and the one that’s really easy (I can’t remember if it’s DKim or Dmark) most domains accept mail from you. I really didn’t have a hard time setting mine up and I’ve done it multiple times. Dovecot is a bit of a pain if you really want imap... but overall none of it is harder than most other things.

> most domains accept mail from you. And this is precisely why I don’t think it’s worth it. I don’t want to have to worry that “most” domains will accept my mail, I want a big email service that has the clout to force domains to accept my mail. I shouldn’t have to solve the mystery of why my mail was rejected (or rather, why some provider thinks I’m sending spam). That’s why I do Fastmail.

What do you use for automated messages (ie, login emails, password resets)?

I asked Fastmail support, and they basically said, "we're not really built for that." However, most of the other services I looked at had arduous terms (arbitration agreements), and even they were talking about delivery rates in ranges of 85-95%.

My takeaway has been that as an app creator, email is really unreliable, and I should try whenever possible not to make it a critical part of anything I build. If 5-10% of the people using your service can't get a password reset email, what do you do?

As someone without much experience with email of that nature, it doesn't seem like the major services actually solve the deliverability problem. If they have Google-style support where I can't get one of them on the phone if my emails aren't sending, then I might even be worse off using them rather than my own setup that I can at least debug and experiment with.

Re: The “mail is hard” myth

#74

Post by brianpgordon »

akerl_ wrote: post #34
SahAssar wrote: post #25

Earlier quoted context omitted.

This is also talked about in the article, is your experience to the contrary?

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…

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

#75

Post by scarface74 »

acidburnNSA wrote: post #37
number6 wrote: post #35

Earlier quoted context omitted.

Running my own for about 2 years now. Spf dMarc and dkim set it is accepted by all mail providers. I also get daily reports from Google how well it behaves

Same here, except to Charter, who has apparently just blacklisted swaths of DigitalOcean IPs, probably for some reason. So I just can't email my mom. Other than that, a great experience.

Except it doesn’t work to send an email to someone who I assume is important to you - “it’s a great experience”.

Isn’t that an argument for why you shouldn’t run your own mail server?

Re: The “mail is hard” myth

#76

Post by esotericn »

brianpgordon wrote: post #74
akerl_ wrote: post #34

Earlier quoted context omitted.

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…

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…

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

#77

Post by scarface74 »

Izmaki wrote: post #14
roel_v wrote: post #4

It's not 'hard', it's 'a gigantic pain in the ass' which is (in normal word use) one form of 'hard'. Which is why most sane people stopped doing it themselves say 15 years ago. Especially for the few cents you can get professional 3rd party email hosting for. Edit: I also very much like the disingenuity of articles saying 'X isnt' hard! Just execute these 20 commands!' Duh, executing those commands isn't the problem,…

Your comment is perfet. Let me quote: "OK, then why is everyone saying it’s hard ? [...] Another reason is because it used to be hard a long time ago. People got traumatized by how hard it was to not screw up and never reevaluated the situation. Some people today genuinely discourage other people from running their mail server, citing the very real difficulties they faced over a decade ago, far before some of today’s…

How does running my own mail server save me time, money, or give me capabilities that I don’t have by paying someone else? What other criteria should I use?

Re: The “mail is hard” myth

#78

Post by bad_user »

xrisk wrote: post #72
rpcwork wrote: post #68

Managed mail server clusters for years with an ISP. Agreed, too many things that can break and cause PITA. However, ‘Hard’ is a subjective term. The deeper you are in a trade or the longer you have done it, the easier it comes to feel. I visited a family farm and found it very very hard to squeeze milk outta buffalo. My great uncle however has dealt with that buffalo that for years and didn’t sweat it one bit. In a s…

This is a great analogy. Why do more work when you can get the same result with less effort?

If you're living at the country side, producing your own milk is healthier, can be a good hobby while you're young and a great occupation after you're retired. Manual labor is good exercise and can be fulfilling.

But I'd probably go with goats instead.

I don't think maintaining your own email server can be very fulfilling, but hobbies are a matter of taste.

Re: The “mail is hard” myth

#79

Post by [deleted] »

brianpgordon wrote: post #74
akerl_ wrote: post #34

Earlier quoted context omitted.

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…

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…

[deleted]

Re: The “mail is hard” myth

#80

Post by bauerd »

danShumway wrote: post #73
xienze wrote: post #62

Earlier quoted context omitted.

> most domains accept mail from you. And this is precisely why I don’t think it’s worth it. I don’t want to have to worry that “most” domains will accept my mail, I want a big email service that has the clout to force domains to accept my mail. I shouldn’t have to solve the mystery of why my mail was rejected (or rather, why some provider thinks I’m sending spam). That’s why I do Fastmail.

What do you use for automated messages (ie, login emails, password resets)? I asked Fastmail support, and they basically said, "we're not really built for that." However, most of the other services I looked at had arduous terms (arbitration agreements), and even they were talking about delivery rates in ranges of 85-95%. My takeaway has been that as an app creator, email is really unreliable, and I should try wheneve…

Keyword is transactional email. I've good experience with Postmark, Sendgrid and Mailgun. Not affiliated, but never had delivery problems
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