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The “mail is hard” myth

poolp.org

141–150 of 311 posts

Re: The “mail is hard” myth

#141
Lately I've been having issues sending mail to Linux kernel mailing list, mail was just rejected and not sent through Gmail SMTP server.

After countless attempts to fix that or to understand why Google think I'm spamming I set up my own mail server on DigitalOcean Droplet. I used mailinabox and the setup was a piece of cake. it works flawlessly now.

Re: The “mail is hard” myth

#142

His assessment on how “Big Mail Corps” accept mail is plain wrong from my experience. When I ran my own mail server, I had SPF, DKIM, rDNS and strict DMARC setup correctly, and got 10/10’s on mail-tester.com. Admittedly my main problems were with people on Microsoft hosted emails. They seem to run some kind of IP address based blacklist-by-default operation. My emails to Hotmail/Outlook.com users would randomly get e…

I run my own, but from time to time large blocks of IP space on Digital Ocean seems to get put into some blacklist. My solution was to use a fallback delivery through SendGrid and their free tier (happens rare enough, and my volume is low). Postfix handles this nicely for me.

Re: The “mail is hard” myth

#143
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…

> 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 Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it. In fact, I used to think exactly like you when I originally set up my personal mail server and opted fo…

I think that because I tried it and my outgoing emails weren't being delivered.

Big mail companies have blacklisted entire C-blocks of IP addresses at VPS providers, because parts of those blocks have been used to send spam in the past, and you won't know until you actually check with people you are sending mail to, to ask if they've received them. It sucks.

Re: The “mail is hard” myth

#144
post #72
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?

Because it is not the same result.

Yes, it is a similar result, but not the same. You give up a lot of control even using a smaller email service provider -- not the least of which is direct control of your own email data. Obviously, since it is email, there is nothing you can do about what others do with emails once they are received on their end, but it is still nice to have direct control of your side.

The counterpoint, however, remains valid. There is some work involved in maintaining your own mail server. If you use a provider, you don't have to deal with any of that -- it's always about tradeoffs. As the article says, however, maintaining your own mail server isn't as hard as a lot of people make it out to be. It takes a little of your time, but once you know the few things you need to do, I find it to not be a big deal at all.

Re: The “mail is hard” myth

#145
post #105
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…

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.

You're forgetting DMARC.

Re: The “mail is hard” myth

#146
TFA is so wrong on so many levels, I do not even know where to begin with. It surely does not make me want to rush to test the author's MTA.

Unless he's talking of a one mailbox server, accepting outgoing only from localhost and somehow endowed with a non residential ip (or good luck with rdns, rbls, etc.). But that was always trivial, post UUCP era.

Background: I've been running mail servers from 1996, several different MTAs, for my company and for customers. Getting the thing up and running is not (very) hard -for a primary MX net facing machine. That's where work begins though.

My primary MTA is still sendmail, and sendmail.cf was never one of my problems - I do not have a degree in compilers, whatever that is, and surely I never read sendmail.cf

Re: The “mail is hard” myth

#147
post #144
post #72

Earlier quoted context omitted.

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

Because it is not the same result. Yes, it is a similar result, but not the same. You give up a lot of control even using a smaller email service provider -- not the least of which is direct control of your own email data. Obviously, since it is email, there is nothing you can do about what others do with emails once they are received on their end, but it is still nice to have direct control of your side. The counter…

Setting up offlineimap to backup your mail is easy. I run daily backups of my protonmail account so in the even they decide to do something nasty to my account, I wouldn't loose more than a day of mail.

Re: The “mail is hard” myth

#148

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…

https://mailinabox.email/ does everything and more. Of course, this doesn't make it easy. You still need to do more things than were you to simply use protonmail/fastmail/etc.

Re: The “mail is hard” myth

#149
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…

> 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 Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it. In fact, I used to think exactly like you when I originally set up my personal mail server and opted fo…

Not GP, but it matches my experience: with reverse DNS, DKIM, SPF, being in DNSWL (and not in DNSBLs) some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance). A while ago there were strange issues with Google-hosted mailing lists as well, with some messages not being visible even to an ML administrator, while Gmail servers accepted mail just fine (maybe it still happens, I'm just not writing to those). I hear similar stories from other mail server administrators too.

I think it's more of a Gmail/BigMailerCorp issue, and still using a private mail server myself, but I don't think it's fair to say that it's all easy and works flawlessly, even with strangely behaving mail servers on the other end.

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