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The “mail is hard” myth

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Re: The “mail is hard” myth

#31

Post by roel_v »

swiley wrote: post #11
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,…

Eh, it used to be pretty bad but the other year the people from the openbsd project wrote a new mail server with a trivially easy to understand config file (I wrote mine from scratch just a couple hours after finding it.) If you’re already basically competent with the OS you’re using and have a machine with a decent connection that can be used for mail then it actually isn’t hard.

The config file format is the least of your worries (unless you're running Sendmail, ofcourse). It's about havimg to know about DKIM/SPF/dns weirdness/ etc, and having to stay up to date; about blacklists and greylists and the social dynamics around it; about mailbox storage and backups and users complaining about quotas and attachment sizes and that sort of shenanigans; about how will I let my users set auto responders and filters etc (just send them a link to the sieve man page! Lol); about having to worry about being called over the holidays because every custom server has its own peculiarities. And his talk about 'it used to be hard but not any more!' - yeah sure, just like the dozens of times people said that over the last decades? There's a 'year of Linux on the desktop' analogy in here somewhere.

Re: The “mail is hard” myth

#32

Post by klingonopera »

ridaj wrote: post #27

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 n…

What exactly changed in the last ...5? 10? years that has simplified the process?

Re: The “mail is hard” myth

#33

Post by wolco »

the_jeremy wrote: post #29
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.

That's a bug with gmail and those who use gmail should be aware they may be missing emails.

Re: The “mail is hard” myth

#34

Post by akerl_ »

SahAssar wrote: post #25
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?

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

#35

Post by number6 »

the_jeremy wrote: post #29
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.

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

Re: The “mail is hard” myth

#36

Post by ChrisMarshallNY »

Everything is easy to folks that have the time to grok the tech.

I like to write software. I don't like running a Linux server, although I know that i could learn to be an excellent admin. It's just that every second I spend learning Linux admin, is a second I'm not spending learning Swift.

So I just use shared hosting for my sites; even though I'm perfectly capable of running a VPS.

Re: The “mail is hard” myth

#37

Post by acidburnNSA »

number6 wrote: post #35
the_jeremy wrote: post #29

Earlier quoted context omitted.

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.

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.

Re: The “mail is hard” myth

#38

Post by eythian »

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,…

The article points it out, but it used to be harder than it is now.

These days (for a long time now, really), it's hard to set one up that's, say, an open relay by accident. The default configs are pretty much all you need, just replacing a couple of values with those that are custom. Basically, what you're saying is exactly what they're debunking. Also, the article isn't "just execute these 20 commands", it's deliberately non-technical.

I've been running a tiny Postfix mail server since ... 2000 or so, still doing so today. It had grown in to a bit of a monster configuration over 17 years or so, complete with a custom PHP interface to allow me to add user accounts, etc. I learnt a lot doing that, but a couple of years ago I started it all from scratch, with a default config and writing the config into my ansible setup so I don't have to remember it. It was very easy to do. Since then, I've touched that configuration once.

One thing I will mention because I haven't seen it around enough, and didn't know of it until someone said it in passing: if you're getting smap-trapped by gmail a lot, turn on TLS support for outgoing. Made a lot of difference. For postfix that's just adding:

smtp_tls_security_level=may

to main.cf. Don't know why that isn't default.

Re: The “mail is hard” myth

#39

Post by calvinmorrison »

Work at a email provider. Mail is not "hard", definitely tricky. Deliverability is a problem, spam is a problem. How do I know? We spend a lot of time working to improve on our services because of these issues.

In general : computers don't solve the issue of trust. End of story.

Re: The “mail is hard” myth

#40

Post by joeblau »

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,…

I totally agree with this and this is actually something that my Engineer Brain and Product Brain are constantly in conflict about. I ran gitignore.io for 6 years and it was not "hard" to run. It was two commands on a web server. The problem was when I was on vacation or at work and AWS/Heroku crashed and I got flooded with GitHub issues/Tweets telling me the service as down[1][2]. All of a sudden, I have to go take a look.

Martin Fowler said something in a talk a few years ago[3] and I think it speaks to this exact mindset. This post is lacking any economic reasons for people to run their own mail server — tell me why me running my own mail server saves me time and/or money.

As another tangent, I'm actually looking at running my own mail server. For me, it's privacy which coincidentally is not even mentioned once in the article.

[1] - https://github.com/toptal/gitignore.io/issues/369

[2] - https://github.com/toptal/gitignore.io/issues/2

[3] - https://youtu.be/DngAZyWMGR0?t=460

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