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After self-hosting my email for twenty-three years I have thrown in the towel

cfenollosa.com

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Re: After self-hosting my email for twenty-three years I have thrown in the towel

#221
The Helm email server — funded by future YC CEO Garry Tan’s VC firm, but I bought one before he returned – is a really great compromise between privacy and convenience.

The IP block is managed by the Helm co., they tunnel connections and sell you the (tiny, silent) server and software. Each Helm server generates its own TLS cert, so the tunneling does not violate your privacy (unless it was delivered without TLS, in which case your privacy already vanished upstream).

The only delivery issues I hit are sometimes with Outlook/Microsoft managed domains. It’s been at least a year since I had that issue. When I first bought one someone on gmail had to move a message of mine out of spam, but it’s been fine since. Last I checked their infra is hosted on AWS but apparently they have some screening technique for getting clean IPs.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#222
post #21

The sweet spot for having control over your email while simultaneously minimizing unforseen headaches is to simply own your domain name and point the MX record to whatever hosting provider you want instead of self-hosting a server at home. Same philosophy for exposing a your personal blog of html files or content like mp4 videos. The sweet spot is to focus on buying a domain name you control. Then let Amazon S3, or C…

You are totally missing the simple fact that the number of blessed email providers to choose from is slowly going down. I've seen ISPs with thousands of clients to give up and move the mailboxes to large players simply because their clients' email was ending up in the spam so often that running the support has gotten too expensive.

It's definitely an anticompetitive practice.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#223
post #21

The sweet spot for having control over your email while simultaneously minimizing unforseen headaches is to simply own your domain name and point the MX record to whatever hosting provider you want instead of self-hosting a server at home. Same philosophy for exposing a your personal blog of html files or content like mp4 videos. The sweet spot is to focus on buying a domain name you control. Then let Amazon S3, or C…

I am ashamed to admit that I have no idea how email works. Is there a dumb down explanation of what are the moving parts and how you can achieve that sweet spot?

You send your email through a client. That client then sends (transfers / SMTPs) that email through an MTA either bundled with it or provided by your mail server.

The MTA parses the message, figures out who it needs to go to (To, CC, BCC headers), figures out what servers receives mail for those recipients, and then transfers (SMTPs) it to the server.

What OP is referring to is that the MTA essentially does a DNS lookup for the recipients domain for a record of type MX (Mail eXchanger).

If you own the domain you have complete control over where that mail goes: you own the MX record.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#224
post #160

Earlier quoted context omitted.

The problem to adding a cost to email is that it affects everyone. The amount of CPU power you need to waste to make most spam not viable is so much that it isn't worth it.

It definitely does not - you can allow different work loads for different senders. Mailing lists you actually want can be dropped to zero for instance. Most spam comes from new address pairs, not existing ones. Requiring high cost to get past a first-contact filter, then near zero forever after, is completely reasonable and would practically eliminate unsolicited spam.

But now the sender needs to know the receivers policy and if they remember that there has been contact before. Or I guess you change SMTP but we still allow unencrypted connections so good luck with that.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#225

> So, starting today, the MX records of my personal domain no longer point to the IP of my personal server. They now point to one of the Big Email Providers. A MX records don't have to point to an IP; it can point to a host name. My MX record is a dynamic DNS host name. > Big email servers permanently blacklist whole IP blocks and delete their emails without processing or without notice. Some of those blacklists are…

Unless you're doing something special, there is a big difference between sending your mail to the recipient's smtp server and relaying it through you ISP's smtp server. The difference is that if you send it direct the ISP can't read it, because it's encrypted. If you relay it, the ISP can read your mail, and even tamper with it, unless the message itself has been encrypted with something like pgp.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#226
post #4

Is there actually a "big tech" email provider that accepts a message with a 2xx SMTP code and then deletes it? The only one I personally know of never does that. That one also does not use anything like an IP address blacklist. This article doesn't name names, it just waves its hands and throws around some innuendo. But as far as my own personal experience goes, this author has no idea what they are talking about.

> Is there actually a "big tech" email provider that accepts a message with a 2xx SMTP code and then deletes it?

Agreed, that is really broken behavior. Once you accept mail for delivery, it should be treated as a contract to deliver that mail. Rejects during SMTP conversation are fine as they notify the sender and do not generate backscatter.

I have heard complaints that Microsoft's hosted mail offerings accept then silently delete mail. It is somewhat believable, as MS Exchange server would respond 2xx for any message to any (including non-existent) destination address and later spam the possibly spoofed sender with bounce messages. Maybe MS has broken behavior like this in their hosted offerings too? And, rather than fix their software, they silently delete mail since they have finally learned that backscatter is a bad thing?

And, MS o365 allows 'delete' as an option for the centralized spam rules maintained by the admin. These mails are accepted 2xx then silently deleted.

MS does other questionable things on their 'free' hosted offerings to mitigate their abysmal spam filtering. I have a couple burner @outlook.com addresses, and they no longer receive any mail reliably from any sender. MS provides the user a place to whitelist senders and domains, but after wasting a bunch of time whitelisting domains, mail still is marked spam. "Junk" is effectively the inbox on those accounts.

Disclaimer: experience is dated, from a past job, running Postfix MTAs for a large organization and dealing with / mitigating MS issues, but never directly involved with any MS stuff.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#227
post #183

Earlier quoted context omitted.

That is a clever idea but I think it'll still fail so long as email (SMTP) is a fire-and-forget architecture. As long as you have that asymmetry, your SNR is going to suck. If it were a back-and-forth protocol, more like TCP, then you have way more options for congestion control, error reporting, load balancing, and the like. The server can choose to accept the incoming request, ask for more verification, or interrog…

> If it were a back-and-forth protocol, more like TCP, then you have way more options for congestion control, error reporting, load balancing, and the like. The server can choose to accept the incoming request, ask for more verification, or interrogate the client in various ways. That's basically what graylisting aims to achieve.

Yeah, this is essentially a form of greylisting. The difference is (as I understand it, this is fairly outside my domain), with the current setup, MTAs can accept an email, and it ends up getting blackhole'd or spam-folder'd anyways. My hypothetical scheme would put more onus on the first "boundary node" to report on errors/compliance. Basically the MTA tells the client what hoops to jump through, and the client gets some indication what will happen once those conditions are met.

That could be an exchange like: "Sign this nonce, and your message will be vetted", or "this is very suss, you have to do X difficulty hashes to have any chance of delivery, and regardless it'll be flagged as potential spam". Or perhaps just a guarantee on how an action would affects the message's "spam score".

This could be used alongside nested packets/envelopes and various headers/trust levels in a network of trust to give a message some overall trust level.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#228
post #200

Earlier quoted context omitted.

https://news.ycombinator.com/item?id=28196403

There's the catch - VMCs are not a mandatory part of BIMI. Though if you want to establish trust , someone has to be willing to put their name on the line and verify everything required. If you have a better approach in mind, I'm sure a lot of people would love to know.

Trust (by way of VMC) is the whole point of BIMI; it’s what’s in all the marketing copy: The fact that nobody else can send mail with your logo. If you merely wanted to send e-mail with your icon on it, that already existed: the X-Face header has been around for decades.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#229
post #21

The sweet spot for having control over your email while simultaneously minimizing unforseen headaches is to simply own your domain name and point the MX record to whatever hosting provider you want instead of self-hosting a server at home. Same philosophy for exposing a your personal blog of html files or content like mp4 videos. The sweet spot is to focus on buying a domain name you control. Then let Amazon S3, or C…

I am ashamed to admit that I have no idea how email works. Is there a dumb down explanation of what are the moving parts and how you can achieve that sweet spot?

Typically, if you sign up for an email account, you get an email address like skywal@gmail.com or skywal@yahoo.com. Alternatively, if you own/host skywal.com, you can have an email address like skywal@skywal.com served from a computer in your home.

The "sweet spot" is combining the two, where you own skywal.com, and have your email send/receive through Google or whoever. Then, if Google decides to ban you, you just register skywal.com with another company who provides that same service, and you keep your same email address.

That's the broad strokes anyway.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#230
post #22

This isn't actually that hard to fix, it's just that for whatever reason, we seem to frequently have this blindspot that we don't seem to have in other industries. Namely that "do it yourself at home" and "massive oligopolist" aren't the only two options. It's like saying "You can only have hamburgers two ways, cook them yourself or McDonalds." I do the third and it's been great. I let my paid webhost handle it. (hos…

> like saying "You can only have hamburgers two ways, cook them yourself or McDonalds."

and your comment seems to be saying it’s OK if we lose the ability to cook hamburgers at home, because there are other (more ethical) restaurants that aren’t McDonalds. am i misunderstanding?

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