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The “mail is hard” myth

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Re: The “mail is hard” myth

#21

Post by jasode »

The "host-your-own-email-server" being "hard" vs "not hard" is an unresolvable discussion because everybody has a different mental threshold of "hard".

I'm still amused that back in October 2017, a commenter (lucb1e) argued[1] that I was exaggerating the difficulties of reliably sending email but a year later in 2019, he confirmed the same difficulties![2]

The discussions in that thread (May 2019) and today's HN thread (September 2019) contradicts author's claim that mail stopped being "hard" 10+ years ago:

>Another reason is because it used to be hard a long time ago. [...], citing the very real difficulties they faced over a decade ago,

Hosting your own email is certainly not impossible and lots of people are successfully doing it. (Or they they're actually not successful because their outgoing emails are sometimes getting silently spamholed without them realizing it.) In my case, I'd rather expend mental energy on other pursuits (machine learning, learning Swift language, etc) than constantly worrying about a personal email server's "reputation health" and then debugging whatever goes wrong.

[1] https://news.ycombinator.com/item?id=15525505

[2] https://news.ycombinator.com/item?id=19757607

Re: The “mail is hard” myth

#22

Post by tschellenbach »

Fun thought experiment. Let's rephrase hard. If you have to hire a team to manage your email for you, how much would it cost you?

The author of the post just explained how most of his friends think this is hard. I don't think email is very hard. But the ROI of doing this in-house is insanely terrible.

Re: The “mail is hard” myth

#23

Post by swiley »

klingonopera wrote: post #13

Let's see... Postfix, Dovecot, SPF and OpenDKIM on the server-side, each of them with their own config. Then you've got to set up your domain, and domain headers on your domain host. Oh, DMARC is also another thing. Then, most ISPs will outright refuse to accept incoming mail from your IP address, since they've basically changed from blacklisting to whitelisting. So you've also got to relay your outgoing mail via you…

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.

Re: The “mail is hard” myth

#24

Post by swiley »

jasode wrote: post #21

The "host-your-own-email-server" being "hard" vs "not hard" is an unresolvable discussion because everybody has a different mental threshold of "hard". I'm still amused that back in October 2017, a commenter (lucb1e) argued[1] that I was exaggerating the difficulties of reliably sending email but a year later in 2019, he confirmed the same difficulties![2] The discussions in that thread (May 2019) and today's HN thre…

There are also different sets of features people want, some are actually pretty difficult to set up.

Re: The “mail is hard” myth

#25

Post by SahAssar »

skrause wrote: post #16

I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam. Especially if you don't actually send a lot of mail, so you can never really build up a good IP reputation. That's why I generally recommend a hybrid setup: Host inbound mail completely by yourself so that you have full control, but ship off outbound…

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

Re: The “mail is hard” myth

#26

Post by andrerm »

klingonopera wrote: post #13

Let's see... Postfix, Dovecot, SPF and OpenDKIM on the server-side, each of them with their own config. Then you've got to set up your domain, and domain headers on your domain host. Oh, DMARC is also another thing. Then, most ISPs will outright refuse to accept incoming mail from your IP address, since they've basically changed from blacklisting to whitelisting. So you've also got to relay your outgoing mail via you…

And Postifx is not just one thing, it's: smtp, smtps, submission, relay etc... And Dovecot: pop3, pop3s, imap, imaps, lmtp, passdb, userdb, sql, ldap, seive etc.

Look, I don't want Google changing this tomorrow because to something tied to and controlled by them because they don't do evel, isn't faster or people like it, but please, don't say it's not hard because you will be misleading people for sure

Edit: to be crystal clear, I agree with parent but don't agree with op

Re: The “mail is hard” myth

#27

Post by ridaj »

To all the folks answering basically "yes it's hard" I think the headline is a bit clickbaity but there are some interesting takeaways... To summarize, (a) yes it's harder than setting up Big Corp Mail, but (b) a lot of the horror stories are either old or secondhand, and (c) it's a lot less hard to set up than it used to be.

If the suggestion is, why not give it a try, one thing I feel is missed is, how hard is it not just to set up but to run over the long run, when the technology evolves and you have to keep up, and why would any IT manager or CIO want to gamble their careers on this?

Re: The “mail is hard” myth

#29

Post by the_jeremy »

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,…

There's also a huge difference between setting up a properly configured server and actually getting things delivered. The big ones (MS, Google) mark your mail as spam even with SPF, DMARC, DKIM and the like. Even on the service I use (purelymail.com) the low volume of mail and the fact that it's less than a year old means that even when I email them first, the replies are sometimes marked as spam.

Re: The “mail is hard” myth

#30

Post by klingonopera »

andrerm wrote: post #26
klingonopera wrote: post #13

Let's see... Postfix, Dovecot, SPF and OpenDKIM on the server-side, each of them with their own config. Then you've got to set up your domain, and domain headers on your domain host. Oh, DMARC is also another thing. Then, most ISPs will outright refuse to accept incoming mail from your IP address, since they've basically changed from blacklisting to whitelisting. So you've also got to relay your outgoing mail via you…

And Postifx is not just one thing, it's: smtp, smtps, submission, relay etc... And Dovecot: pop3, pop3s, imap, imaps, lmtp, passdb, userdb, sql, ldap, seive etc. Look, I don't want Google changing this tomorrow because to something tied to and controlled by them because they don't do evel, isn't faster or people like it, but please, don't say it's not hard because you will be misleading people for sure Edit: to be cr…

Yes... and ooof!

And then there's also the password/username database, that defaults to tying into the Linux pass/user database, so if you want to set up some custom login-data... ugh, I don't even want to think about it.

I set it up once, maintain it here and then, and am keeping it, because dismantling the system is more work than maintaining it presently, but seriously... with the above setup, do it only for educational purposes.

...I'm guessing I spent a week or so properly setting everything up.

...but I'm also willing to try a universal, one-size-fits-all program, if anyone knows anything for Debian?

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