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The “mail is hard” myth

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Re: The “mail is hard” myth

#181

Post by AlexCoventry »

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…

You might if the supermarket milk was reporting everything you say back to the farmer.

Re: The “mail is hard” myth

#182

Post by MiscIdeaMaker99 »

fit2rule wrote: post #157

Running your own mail server is like having a pet dog. You have to keep it in good shape, exercise it, feed it well .. chain it up when necessary, clean up after it and so on. Keep the neighbours kids from stealing it and using it to deliver drugs, etc. If you treat it like a pet, it makes it a lot easier to manager. "Oh, did I forget to check the mail logs this week", and so on..

I don't see self-hosting email as being any different than any other self-hosting service. I mean, take "mail server" out of our your analogy above, and replace it with "web server," and everything still applies.

Re: The “mail is hard” myth

#184

Post by AlexCoventry »

lonelappde wrote: post #54
jwr wrote: post #49

Earlier quoted context omitted.

> 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 I've been running my own mail server since 2000 or so. It isn't hard, it takes almost no time at all, and I have my own independent mail that nobody reads, and I make the decision of which mail to accept. I will take the liberty of classifying the above comme…

You can use hosted mail with pgp/gpg if you don't want anyone reading your mail. Otherwise your mail is read in transit on the way to you anyway, so self hosting is false privacy.

Isn't most SMTP traffic over TLS, these days?

Re: The “mail is hard” myth

#185

Post by jasode »

amelius wrote: post #125
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…

> 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.

>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

#186

Post by earenndil »

> Let me tell you a secret: Big Mailer Corps are not worried about you but are worried about big senders harassing their users. They do not care about your personal server sending a few mails, even if its in the thousands per months. What they care about is the infected computers or compromised servers flooding their users. What they care about are the marketing companies that are literally shitting over them, sending individually millions of commercial mails per day, trying to work-around spam filters, and that sometimes manage to go for a while without being rejected. Unless you are sending hundreds of thousands of mails to them on a daily basis, quite frankly and without trying to hurt your feelings, you fall waaaaaaaaaaaaaaay below the radars.

This is absolutely not true. A server I had mailed out daily run outputs to local users, and was also configured to send an email to one of the users' gmail accounts. I also used that server for personal email, but eventually had to stop because the daily run outputs got us blocked by gmail.

Re: The “mail is hard” myth

#187

Post by Jsharm »

newscracker wrote: post #151
flurdy wrote: post #112

A mail server is hard. Writing applications is hard. Designing a website is hard. Professional work is hard. But setting up your initial mail server is not hard. Read some guides (ahem: https://flurdy.com/docs/postfix ), fix a lot of typos, and you're up an running. Same with developing the initial version of an application, or designing the first draft. Not rocket science. Not easy but not that hard for an experienc…

> If you just want a reliable mail service, just use... non-Fastmail options that are a lot cheaper for multiple mailboxes and provide more, like Posteo, Mailbox.org, Runbox.com, Mailfence, Migadu, etc.

I never hear Zoho Mail mentioned, I migrated from Fastmail, 1/5th of the cost and if anything slightly better interface as a bonus!

Re: The “mail is hard” myth

#188

Post by nocman »

tschellenbach wrote: post #22

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.

"But the ROI of doing this in-house is insanely terrible."

^ this is far too much of a blanket statement. I've done it, in house, for both personal and work purposes. The cost in my time was not very high, and the ROI was very good.

Obviously there is a much broader range of experiences with managing your own mail server than many on this thread think there is.

Re: The “mail is hard” myth

#189

Post by zelly »

I've done this a couple times, and I think it's sufficiently difficult that if in the future I were hiring for a Linux sysadmin, I'd have them set up a mail server (that doesn't get spamfiltered) in less than 24 hours.

I never got spam filtered once DKIM/SPF/rDNS/DMARC were properly configured. I think _this_ is the myth that Big Email spreads. Linux mail servers are hard, but getting past filters is actually not hard. Spam filters are really good today not just in their true positive rate but also their true negative rate.

Given that a lot of services use your email as a 2FA mechanism, I wouldn't want to use a self-hosted mail server as my _only_ personal mail. You have to have a good reason[1] to make the time and maintenance commitment.

[1] https://en.wikipedia.org/wiki/Hillary_Clinton_email_controve...

Re: The “mail is hard” myth

#190

Post by scarejunba »

defanor wrote: post #174
pw6hv wrote: post #160

Earlier quoted context omitted.

> 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) How did this happen if Gmail deletes spam after some weeks?

Indeed, a quick search suggests that spam is automatically removed every 30 days there. The wording was "Google hid it from me", so either I have wrongly assumed that it's about the spam folder, or it is possible to disable autoremoval. Edit: or, as the sibling comment suggests, it behaves strangely with respect to removal as well.

Or user accidentally archived it. “X did Y” is often a user’s way of saying “I accidentally made X do Y” without having to accept blame. It’s the “dog ate my homework” of excuses.
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