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The “mail is hard” myth

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91–100 of 311 posts

Re: The “mail is hard” myth

#91

The thing I've always worried about is that to my knowledge there's no ACK for outbound mail. The potential impact of one email I send not being received is absolutely enormous to the extent that certain mails I'd pay a decent amount of money to ensure delivery, probably more than an actual postage stamp.

Do you want read receipts or delivery receipts? Both versions exist.

Re: The “mail is hard” myth

#92
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?

This analogy applies to everything and the answer is always the same: if we centralize then we are vulnerable to tyranny. It seems inevitable that we do this though. Human history is a cycle of people investing more and more trust in an authority, then being abused by that authority, followed by a revolt and the installation of a new authority.

Re: The “mail is hard” myth

#93
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?

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

If you wake up one day and the only email you can use is the one you can get from a major provider, you have just become a consumer.

Re: The “mail is hard” myth

#94
post #24
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.

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

That's true but I think if we analyze discussions (see this thread and old threads I cited) of one group of HN experts (email is "not hard") debating other HN experts (email is "hard"), the most contested issue isn't the difficulty of advanced SMTP features and enhancements -- it's about outgoing sent emails being reliably accepted.

Re: The “mail is hard” myth

#95
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?

Q. Why might a single agent stuck in a sub-optimal Nash equilibrium, along with 100s of millions of others, not make a different choice that might cost them more?

A. Ideology. If the agent wants a different global equilibrium, they might decide that them choosing differently, (1) calms their conscience and/or (2) actually make a material different in the choices of others.

Re: The “mail is hard” myth

#96
post #14

Earlier quoted context omitted.

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?

> or give me capabilities that I don’t have by paying someone else?

The same can be said "why should I grow my own veggies when I can buy them from the supermarket?" - The point is always, always, about Freedom.

Re: The “mail is hard” myth

#97
post #10

> but my mails will not reach my users at Big Mailer Corps Unfortunately this is not a myth. rDNS/DKIM/SPF/not in any greylists, but mail from you goes to Junk folder on GMail®, experienced that myself.

It's a bit of a black box, but how do you get around this? Is it a matter of domain age? IP trustworthiness? Or do a lot of people have to categorize it as "Not spam" first?

Re: The “mail is hard” myth

#98
Been there, self-hosted my email for more than half a decade, gave up on it a few years ago for a couple for reasons:

If you are self-hosting the most important authentication fallback for your online identity, an ill-timed downtime or deliverability problem really hurts.

Your reputation can be affected by neighboring bad actors you have no control over. For example, SpamRATS punishes full subnets without an actual appeals process.

From the point of view of a major provider, the same email from your tiny server is going to have a lower score than one from their system. Encountered this a lot against Gmail.

And it's a commitment. If you go the self-hosted route, you will need need to keep up on new security and filtering practices, even if you use a turnkey solution. You might get bored with this after a while.

Re: The “mail is hard” myth

#99
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 would also recommend setting up a dmarc record so you can monitor your deliverability.

Spam however is still a hassle and you're never going to match Gmail or Outlook when you're small. Say it takes a few hundred identical spammy emails to trigger a filter. For Gmail it means the chance of receiving that spam is less than 1 in a million. If you're small and managing say a 1000 users - a large percentage will end up with receiving the spam.

Re: The “mail is hard” myth

#100

OT: Thunderbird org should create/sponsor its own email server software. That's the way to spur email development by causing development on both sides of the chain. Sometimes in unison. And they should also initiate an email service to put their development in action. Imagine the innovation that could happen then. - Email encryption standards for key acquisitions - folders/labels stored as imap keywords - large file…

I disagree. There is next to no code sharing between the server and client side of email--implementing the server side of the protocol is vastly different than the client side, and even the server-server versus server-client sides of SMTP and NNTP are practically different protocols. Furthermore, Thunderbird already struggles to get enough developers to avoid compounding on its technical debt; such a large undertaking is simply not possible with the current manpower.

I'll also point out:

> - Email encryption standards for key acquisitions

This is basically a standardization problem. I've been involved in at least one failed attempt at standardization here.

> - folders/labels stored as imap keywords

The difficulty here is knowing when you can opt-in to this functionality, which is again basically a standardization process.

> - large file sending protocol using third party services

Thunderbird already supports this, and has for... 7 years or so?

> - msg retrieval when email severs experience outages

If I understand this right, this is basically having your MUA duplicate emails locally... which is what most MUAs do these days (at least on desktop).

> - development in mail list servers.

What development are you talking about? Mailman is pretty actively developed, they even had a GSoC project a few years back to add encrypted mailing list support.

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