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Discussion Sentiment

52% Positive

Analyzed from 4058 words in the discussion.

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#email#spam#self#server#mail#hosting#llm#don#writing#years

Discussion (132 Comments)Read Original on HackerNews

Leonard_of_Q•about 1 hour ago
Does it or is this part of the push to keep people from hosting their own email services? I've self-hosted email for about 35 years now and see no reason to stop, it hardly ever needs maintenance and my mail tends to arrive even at hostile destinations (Micros..., Ggl, ...). Don't listen to those who fight against decentralisation, their agenda does not match yours.
layer8•41 minutes ago
Same here (well, 25-ish years). And while self-hosted email may be declining, it apparently still outnumbers any single email provider: https://labs.ripe.net/images/r_uuIdAmmdbhI1R9Der6slvvH5U=/10...
cube00•32 minutes ago
Especially someone who stands to gain if they just need to get cosy with two email providers to deliver their spam.

(Blog author) runs the email infrastructure measurement project at Live Direct Marketing

Google offers "mail merge in Gmail to send personalized email campaigns, newsletters, and announcements to a wide audience." [1]

Based on how much @gmail.com spam I used get within GMail I can only assume they treat mail from their internal accounts much more favourably then us dirty self hosters.

[1]: https://support.google.com/mail/answer/12921167

Arnt•15 minutes ago
I follow the standards processes, and while I don't see a push to against self-hosting mail, I do see a push to stop storing cleartext passwords. Which is typically what your MUA uses to access those self-hosted mail servers.
Gud•18 minutes ago
I've been self hosting myself now for a couple of years(after a brief, 20 year hiatus) and it was less difficult than I though it would be.

Don't listen to the naysayers.

throwaway67743•about 2 hours ago
I'm sure it's a good article but there is no need for it to be written by an LLM... Is everyone really this lazy now? I don't think I've read anything written by a human for at least a full month.
flyingcoder•about 2 hours ago
This seems like a load bearing issue. Would you like me to put together a plan to put human-written text in your daily routine?
throwaway67743•about 2 hours ago
Oh you.
frereubu•about 1 hour ago
I really wish there was an HN guideline that I could point to which says that you shouldn't complain about LLM writing, in the same way that's there's guidance on site annoyances:

"Please don't complain about tangential annoyances—e.g. article or website formats, name collisions, or back-button breakage. They're too common to be interesting."

LLM-written content is now too common to be interesting and complaining about it does not make it stop, it just derails comment sections. The reptitive complaints are getting as annoying as the LLM-written content!

genxy•13 minutes ago
Why do you give up so easily? Human culture and the already low quality bar of writing should be allowed to fall even further because you are annoyed by those that want to protect it?

Why should your opinion be worth more than those who would like to retain a semblance of meaning in what we use to convey ideas? LLM writing is sheer trash. It comes off like a coke-addled car salesman who is making a pitch to VCs about his latest scientific discovery that will 200x their investment.

Poorly written LLM content is NOT a tangential annoyance. If this is too much, maybe you should simulate HN using

Generative Agents: Interactive Simulacra of Human Behavior https://arxiv.org/abs/2304.03442

ViktorRay•about 1 hour ago
Wait isn’t there actually the opposite HN guideline? In that LLM generated content is not allowed here?
zenoprax•43 minutes ago
Comments are for humans but I don't think there is any reason for HN to police the submissions as a policy. If any article lacks credibility or merit to the extent that one can't even finish reading it then just ignore it and move on. Vote for something else. If "LLM aversion" is your rationale, so be it.

Personally, I usually check the comments before deciding to read something so I appreciate that others have saved me the trouble of reading this article in particular. If the author doesn't care enough to use human time to write it then I am not going to use human time to read it.

frereubu•23 minutes ago
LLM-generated content is not allowed in HN comments, but it doesn't mention submitting links to LLM-generated content. This is the only mention in the guidelines: "Don't post generated text or AI-edited text. HN is for conversation between humans."
nik282000•about 1 hour ago
If the "author" didn't feel like taking the time to write the text why should I take the time to read it? LLMs are great for summarizing, if you are going to slop 100% of a document make it a summary and save us all the time.
frereubu•37 minutes ago
Fine, don't read it, but also don't comment about not having read it!
greekrich92•44 minutes ago
This is a breathtakingly dumb idea
frereubu•36 minutes ago
Thanks for the constructive feedback.
cryo32•about 1 hour ago
I have people writing emails to me with an LLM now. We've gone from meetings where "this could have been an email" to emails where "this could have been a few carefully chosen words, not a rambling diatribe which would test the most hardcore Tolstoy fan".

Kill me. With a spoon. Slowly.

mherdelight•about 2 hours ago
Are we even sure the actual stuff in the article is real? What if it's just the usual LLM hallucinations
jstummbillig•about 2 hours ago
> Is everyone really this lazy now?

Everyone should aim to be this lazy. Everyone is trying to maximize their time. This is what software has always done. It helps people be lazy in some respect, and then, so far, we have always found new stuff to do with the time we freed up.

LLMs got decent at writing, and before long they will be better at write-ups than the average human writer and we won't look back.

Of course, this is contingent on your current goal: If you want to get better at writing, you should do the writing, just like you want to do the math, if you want to learn multiplication. Writing is fine as a tool just to get information across. It needn't be more than that for everyone.

conception•about 1 hour ago
The problem is LLM output’s value is intrinsically zero because there is no scarcity to it. I too can just prompt “What’s the rate of self hosted email?”. If an article is signaling that its value is zero, then everyone should just move on as it’s not providing anything to anyone. Effort is the economies main signal of value, good boots that last cost more in the classic example. The only time it’s not zero is when there’s a shared understanding between those consuming the output - a company wanting your llm code, friends making funny images for an inside joke to share, etc. And some people grouped may be specifically interested in AI output - people sharing music on Suno. But in my experience no one cares about your AI generated song, image, article, app if it appears to just be my own prompt away from me having it too. Give a significant other an AI image printed out for an anniversary gift - see how excited they are about it. Versus getting an artist or photographer to do the same. As Claude might say, it’s not laziness, it’s effort.
jstummbillig•about 1 hour ago
> The problem is LLM output’s value is intrinsically zero because there is no scarcity to it.

I think if this post had not gone the AI-generated-text-route, some people here would easily have considered it interesting for its content, even if it was entirely AI generated.

bastawhiz•about 2 hours ago
And soon, I'll be lazy and use an LLM to do the reading for me. Eventually the LLMs will train on the state of the world and decide to be lazy also, and the "writer's" LLM prompt will just be shared with the "reader": nobody actually needed all those words anyway! Maybe someday we'll get rid of the links on HN and we can just share and consume headlines.
RobotToaster•about 2 hours ago
>LLMs got decent at writing,

Judging by people's response, that doesn't seem to be the case.

> and before long they will be better at write-ups than the average human writer and we won't look back.

I'll read articles written by them if and when that happens, but not before.

bluGill•6 minutes ago
What does "decent at writing mean"?

When you start digging in you realize that (like most things) there are multiple different definitions. LLMs are very good at putting together a lot of words that are spell correctly with grammatically correct sentences (better than me - though I'm particularly bad at this). However people often want to add other things like "correct" (the facts are right...), or some notion of not using too many words. LLMs tend to not be as good at those.

Arnt•19 minutes ago
Friends of mine say that internal reports from their workplaces are often worse.
bilekas•about 2 hours ago
Efficiency and lazyness are two very distinct things. As is quality and quantity.
Yizahi•about 1 hour ago
Isn't that a variant of utilitarianism basically? The only things worth doing are the ones which allows us to do less.
mc32•about 2 hours ago
The ability for people to communicate is paramount. Without the ability to communicate there is no progress. We might as well be deaf, dumb and perhaps blind.

Delegating this task to automation serves to undermine all the masters and indeed strengthen the servants.

Short term this offload is good for people; long term it’ll lead to mental rot where people are hard pressed to put their ideas forward and give up in exasperation when they don’t have the assistance of their servants. Their ability to even make the proper requests to the servants may deteriorate enough that their existence may come to rely on the benevolence of their servants.

ferngodfather•about 2 hours ago
> The domains didn't disappear; they moved.

I stopped reading at this point. I cannot emphasize how much I HATE this AI writing style.

cube00•29 minutes ago
> Dictionary-based classification has a ceiling, and I want to be honest about where it is.

I stopped here, anytime an author (or likely AI) feels the need to tell me they're being honest or "genuine" I don't need to read any further.

I'll assume honesty but the minute you explicitly tell me, you've probably got an angle that I'm too dumb to see, but I'm not dumb enough to keep reading.

gr•39 minutes ago
Wait, what makes it AI and hateful, the `;` there?!

Is this in the same vein as using — em dashes?

Are people with minimal regard to typography and style doomed to lower their standards because the masses can't even?

xtracto•33 minutes ago
To me, what makes it hateful is that it is EVERYWHERE. Reddit is full of it, LinkedIn is full of it, the web is full of it. Shit, even Facebook has it now.

It's kind of sad. I compare it to when Memes started becoming popular as communication tools on the internet (mid 2000s from what i recall): Instead of writing text to convey the idea they wanted, people just pasted a meme (my face when ... whatever).

Now with AI, everyone write everything in the same way.

ferngodfather•16 minutes ago
It's the semicolon and the phrasing together. I can't explain but after you use AI a little you just notice the way it 'writes'.
stavros•about 2 hours ago
The need is that writing is expensive. An LLM is around a hundred times cheaper than a human, so this kind of article that doesn't provide tons of value just makes sense to write with an LLM.

I hate LLM writing, but the economics checks out.

mrweasel•about 2 hours ago
> The need is that writing is expensive.

That's the thing, good writing is expensive, massively so, much more than people think.

Letting the machine do the writing however shows us that many people have no idea why writing is expensive, nor do they respect that perhaps it needs to be expensive. Communication is incredibly hard, very few master it. I'd even go so far as to say that clear, precise and readable communication is so hard that we do not have sufficient training data to build an LLM that can do it.

Letting a person write article, like this one, doesn't necessarily improve the quality, but it does show us that some thought and effort have at least been put into it. There was a cost and you deemed that cost worth it for conveying your message. Without the cost there's nothing stopping you from wasting peoples time.

throwaway67743•about 2 hours ago
That might apply to some things, but there is little to no value in this article, so the economics are the same as the spam - cheap to spew garbage while providing no value and wasting the readers time. It's not something that should be encouraged. RIPE should know better.
iLoveOncall•about 2 hours ago
How about not writing the article at all then?
stavros•about 2 hours ago
Because people will read it if you write it, hence us being here.
A_D_E_P_T•about 2 hours ago
I wish there were a way to self-host without my emails constantly getting stuck in other people's spam folders. And it made me really paranoid about email, too -- like I'd send emails, and I'd never know if the other end received them or not, unless they replied. Without a reply, I would always wonder whether the message got a look, or disappeared without a trace.

The only way around this seems to be hosting with Google, Microsoft, or maybe Proton. Any other ideas?

PaulRobinson•36 minutes ago
It feels like the only way to stop this happening reliably, is to get as many people as possible off Google and Microsoft.

I'd argue that self-hosting is the first step. The second step is helping everyone you know get their own domain and host their email for them. If they don't trust you to not read their email on your server, point them to somebody else who offers mail hosting.

The more people we can convince the internet is something anyone can help build outside of the silos, the more likely it is to survive.

groomlake•about 1 hour ago
I ended up switching to Fastmail a few years ago, but before that I was relaying outgoing email through Amazon SES. It fixed all my deliverability problems. Before that, when sending from my own server, emails might just not show up. Not in recipient's spam folder, not rejected by their server. Accepted and then dropped mysteriously.

If I ever go back to self-hosting email, I would do the same except I would maintain a whitelist of friendly mail servers to which I would send directly. Or maybe just relay emails to Google/Microsoft via SES and send the rest directly.

iamnothere•37 minutes ago
Use DKIM on a long lived domain, and check that your sending IP is stable and comes from a block with good reputation. This has always worked for me.
layer8•25 minutes ago
I haven’t had this issue. It might be due to the long-standing reputation of my email domain(s) or of the mail server’s IP address, I don’t know. But I know other self-hosters who don’t have that issue either.
cjs_ac•about 2 hours ago
I started self-hosting my email last year, but I use MailPace (other email sending services are available) to avoid being memory-holed.
frizlab•about 2 hours ago
I use fastmail which is very good. Like “oh this is how it should feel!” good.
MikeNotThePope•about 1 hour ago
I only have one minor complaint about Fastmail after 5 years. I can’t do a full-page screenshot of a long email on my iPhone.
hdgvhicv•about 2 hours ago
I don’t self host, I pay zoho to do it. Over never had any suspicion my emails haven’t been received.
jml78•about 2 hours ago
It happens on zoho. I ran my business email on zoho. Multiple instances where people on Gmail had my messages go to spam. I have the same issue with proton mail.
the_real_cher•about 2 hours ago
I think that is the Crux of the issue.

Email spam has made self hosting untenable.

sharperguy•about 3 hours ago
If someone can solve the spam problem in email without just manually whitelisting specific providers that heavily monitor their users, then they can completely reverse the direction of this problem. Unfortunately it doesn't seem likely someone could do that.
abirch•about 2 hours ago
It's not in the current providers' interest to help people avoid the current providers' advertisement or avoid paying the providers to host the customers' email.
andrewchambers•about 2 hours ago
Seems like AI is in a pretty good position to do that tbh.
avian•about 2 hours ago
> DMARC: adopted everywhere, enforced nowhere in particular

Unfortunately this only talks about what DMARC policies are published by domains. I was hoping they will go into some analysis of how many mailboxes actually hard-enforce DMARC rules on ingress (as in, respect the DMARC policy as published by the sender's domain, p=reject or whatever else it might be)

I have been hesitant to enforce DMARC rules on my server. Partly because maintaining it was a pain (see opendmarc - maybe better with rspamd now), but also because on my test runs I saw plenty of legitimate incoming mail that simply would get rejected if I were to enforce DMARC on ingress.

I suspect big players like gmail have some kind of soft enforcement/reputation/machine learning approach to DMARC, but this is way too much work for a small time admin like me.

skeledrew•about 1 hour ago
I've been using GMail roughly since it existed I think, and have thought on and off over the years about self-hosting. The notion scares me every time because with it comes thoughts of what would happen if I were to lose the domain name or server, or even if there was an outage at the "wrong time". And then there's also the idea of updating the 1 million+1 services, etc that I used it to sign up for. As much as I'm not a fan of a decent amount of what they've been doing, they're however a stable entity which offers a very reliable service for essentially free. Very likely that many others also think along those lines.

The only thing I think can compete with that is some kind of decentralized solution, also something I've thought about a bit. Like a Keyoxide-based[0] - or similar - setup that makes it virtually impossible for one to lose their online identity (since lost keys can be rotated out once one has - access to - enough proofs), and then that identity can be used - without fear - to route associated data, etc. Of course adoption of what could become an adjacent or new standard would be the next hurdle to overcome...

[0] https://keyoxide.org/

IsTom•about 1 hour ago
> what would happen if I were to lose the domain name or server

On the other side of the coin, what would happen if google bans you? That's certainly not unheard of.

skeledrew•about 1 hour ago
True, something else I've considered. But the reported incidents are few and far between, and the stories always have some trigger. I have been taking small steps to move away, though it's yet another service where "stuff" could happen: since DuckDuckGo introduced their proxy email service I got one and have been using it for my more recent sign-ups. So if something does happen to the GMail or I hit some switch-over threshold, I can point it elsewhere, though everything before would be lost.
defaultcompany•about 1 hour ago
If Google bans you they at least will not hand out your email address to someone else. If your domain expires and someone else registers it that’s essentially what’s going to happen.
gommm•about 2 hours ago
I've been running my own email server with exim and dovecot for 20ish years, I like the freedom it gives me but I have to say it's a significant investment. Not so much keeping things up to date but instead making sure that my emails are actually delivered. I've eventually switched to using fastmail just for sending emails and even with that, I don't get perfect delivery.
mrighele•about 2 hours ago
Last year I started self hosting my email. I found that once you setup the “usual suspects” (DMARC, DKIM, SPF…) outgoing mail works without issues. In fact it works now better than the (small) provider I was using before.

And setting them up properly is not even that difficult nowadays

groomlake•about 1 hour ago
Whenever HN discusses self-hosting email, half the people with self-hosting experience say they never had any issues and the other half says they had so many issues they had to give it up.

I self-hosted for years and I did all the standard things you're supposed to do, but I had tremendous problems with Gmail and Outlook. Other providers usually went through without issue.

mrighele•11 minutes ago
I guess there is a certain amount of luck in this, probably related to the provider, or the range that your IP reside into. (I guess google and microsoft keep their own blacklists, regardless of what public blacklists say). I wonder if the best course of action in that case is to just spin up a new server on a different provider and try again.

FWIW, in my case, I am running the server on Hetzner, even though is supposed to have a bad reputation, but I have been using its IP for more than 10 years for other things (web server, personal services etc) so I guess that helps

weavie•about 1 hour ago
How much of this is just down to your mail server being randomly assigned an IP address with dubious history or not?
smalltorch•24 minutes ago
On the other hand, I'm working on a prototype to completely throw away conventional email. Creating a system where you can simply spin your own physical mail box and node, and reach others at their unique address.

https://gitlab.com/here_forawhile/tmail

lazyweb•about 1 hour ago
Hosting a personal, low volume mail server works as well as ever. If you know what you're doing.

I've written about it five years ago, still applies: https://schumacher.sh/2021/05/10/running-a-private-mail-serv...

VladVladikoff•about 2 hours ago
20 years of running the classic postfix + dovecot stack for about 10 business domains. I’ve recently been testing out stalwart, with just one company domain, which is nice but seems quite fragile, 4 times now it’s killed itself doing some self updates. If it wasn’t for Claude assistance I probably would have given up on it by now. It is quite feature rich though, but its spam detection is not great, too much ham flagged as spam, not enough spam flagged as spam. 2FA is a nice bonus but for some unknown reason it breaks itself every few weeks and I gotta turn it back off again. If I could get stalwart stable I would migrate all my domains to it.
raddan•about 2 hours ago
Why switch then? Need more excitement in your life?

I have been running Postfix for 22 years, from a big corporate installation to my own on a Raspberry Pi Zero. It just does its job.

VladVladikoff•about 1 hour ago
2FA is a big one. We need it to please the insurance companies.
bilekas•about 2 hours ago
Mail self hosting is not an easy process to maintain.. If you do manage to get whitelisted you need to ensure you're on top of maintaining it, let alone some larger provider like Google just deciding they don't like you. I do empathise with wanting to self host, I just always found the cost of effort to do so really didn't offer enough benefits versus a good provider like proton for example. It sucks but maybe a fight that's too far gone to win.
agentultra•about 2 hours ago
It’s not that bad, but it does require some effort. I self-host. I spend far more time using and enjoying email than I do maintaining the infrastructure.

However you do have to live with the occasional blacklist when you host on a VPS like I do. Some idiot in your IP range may get blacklisted for spam and then you get caught in it. It’s generally temporary.

And there are some corporate policies that will flat out reject emails from you which is fun.

I’ve probably spent less than 10 hours over the last 5 or 6 years on maintenance.

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IFC_LLC•about 2 hours ago
The hardest thing in setting up your emails server is to keep your messages out of spam folders. Even if you are completely legit company that sends out ONLY human-written personal emails, you will get tagged as spam first.

I've self-hosted for about 2 months, and promptly switched to iCloud. Just because I've been spending too much time calling people and telling them to check their spam folders.

Recently our business moved to another domain. We had a guy who has spent over a month "warming up" traffic, so our new domain won't be tagged as spam by default.

FriedrichN•about 2 hours ago
Self hosting is not that hard actually.

The problem lies with the big e-mail providers marking your e-mail as spam, even if you have everything configured right (MX, SPF, DKIM, DMARC, etc.) and you're not on any blacklists. They use their mysterious opaque algo to determine that your e-mail is spam and you have no idea what you could do to not get in peoples junk boxes.

sshine•about 2 hours ago
> They use their mysterious opaque algo to determine that your e-mail is spam and you have no idea what you could do to not get in peoples junk boxes.

And that’s not hard?

Running a modern mail server, a spam filter, a self-hosted webmail, and learning just enough about DNS and networking to get mail through: this is what’s not that hard.

Figuring out how to stay whitelisted, or accept ending up in people’s filters, asking them to whitelist you while your public IP gradually gains trust, is a job.

FriedrichN•about 2 hours ago
That's pretty much what I mean. Implementing the authenticity measures is very easy, making sure the e-mails get delivered to peoples inboxes without getting marked as spam is hard.

I just wish these big parties would give you a more formal way to make clear you're not a spammer.

liotier•about 2 hours ago
At this point, self-hosting email is as much a practical convenience as it is a political statement. Or maybe I'm just stubborn.
DogRunner•about 2 hours ago
And on the other side, projects like stalwart email ( http://stalw.art/ ) and mox ( http://xmox.nl/ ) makes it so much easier to build an e-mailsystem on your server.
Scarjit•about 2 hours ago
I have deployed stalwart as my replacement for mailu and iv never had such an easy time setting up mail, i love it.
63•about 1 hour ago
Like many others, I gave up on self hosting email when I realized Gmail and Outlook would always mark me as spam, if I even got delivered. DMARC and DKIM did nothing, I think the datacenter IP was just blacklisted. Ostensibly there are ways to get it unblacklisted but man what a pain the ass for the whole process.
petcat•about 2 hours ago
Spam ruined email. It's really as simple as that.
gglitch•about 2 hours ago
Nothing will ever ruin email. A private email server, or a federation of mutually-whitelisting ones, is the ultimate social media, and not at all a bad personal information management system too.

Edit: typo

_joel•about 2 hours ago
I hardly ever see any spam nowadays, happy fastmail user.
redeeman•about 2 hours ago
spam filters are effective at dealing with that
nh2•about 2 hours ago
Not in my experience.

My self-hosted email filters too little spam, while GMail etc filter too much (e.g. important company correspondence leading to orders almost being lost because they landed in our GMail spam).

nik282000•39 minutes ago
Does GMail silently filter spam now? I get maybe 5 new messages in my spam folder per month for the past couple of years and I'm not sure if Google is just dropping the most blatant spam or if my primary address is somehow not on any lists.
brikym•about 2 hours ago
It works both ways right? If you self-host you are seen as the spam.
rdwrrr•about 1 hour ago
To be fair, hosting your own email server is just a pain in the ass.
elendilm•30 minutes ago
No
sandebert•about 2 hours ago
Interesting topic. I wonder if the AI was given notes to base the article on, or if it was given the data and also made the full analysis itself.
dbingham•about 1 hour ago
This is the counter example to "protocols and interop solve enshittification". No, they don't. Email is the model protocol: perfectly interoperable, perfectly decentralizable. And yet it is centralizing in the hands of a few organizations who then wield enough market power to bend everyone else to their will. It's still enshittifying. If email hasn't resisted enshittification, then interoperable protocols are not the solution for it. And yet, pretty much all of the pro-social, anti-enshittification effort in tech is being directed into protocols and interop.
elendilm•39 minutes ago
Recently went self hosted. Not going back ever again.

Also had a couple of ui pages on our app to have full email functionality.

This also means custom integration into our existing ecosystem.

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glum64•about 2 hours ago
Stopped reading at "The MX record says where the mailbox lives."
kypro•about 2 hours ago
I switched to M365 as my provider a few years back as my emails kept being flagged as spam.

I've done it for decades, but I don't know much beyond the basics of email hosting tbh, however my understanding is that these days email coming from self-hosted servers carries a much higher spam/junk risk and so often automatically marked as spam.

Maybe there are ways to avoid this happening, but when a few clients all reported that they were not receiving my emails I didn't have much of a choice but to switch.

rantingdemon•about 2 hours ago
I would also be interested in self-hosting but have limited understanding of what would be required to ensure my email does not get flagged as spam.
ubermonkey•about 1 hour ago
I self-hosted for a while in the early 2000s. It was a hassle. My box got hacked -- I'm sure I missed a security update or something -- and while I didn't lose any data because of my obsessive backup paranoia, it was enough of a Thing that I just punted.

I used Gmail for Domains for a hot minute, but never really liked it very much. Soon I found Fastmail, and I've been using them ever since (so about 13 years now).

gostsamo•about 2 hours ago
Hosting my own server with mailinabox. low traffic, but keeping their random subscriptions, newsletters and occasional single purpose address. Haven't had any issues so far.
logicallee•about 2 hours ago
I run my own mail server, and I am very concerned about its reputation and deliverability. I've run my own Linux server full time since at least 2017, obviously well before LLM's, but only recently put up a mail server. I don't usually run any agents on the server, such as Claude Code, ChatGPT Codex, or Grok Build, all of which I have subscriptions for but don't run on this server. Instead, I manually administer the server using ssh, while getting interactive help from ChatGPT in a chat window.

It was complicated to get security, DNSSEC, DKIM, DMARC right this way. I did it just under a year ago, around September 15, 2025.

I tried to follow and understand what I was doing, and keep good records on it. It was a complicated process, but everything was up and working at the end and I received email my server sent me. It felt good to be able use this simple script to send myself email:

     #!/usr/bin/env python3

     import smtplib
     from email.message import EmailMessage
     
     msg = EmailMessage()
     msg["From"] = "(user's from address)"
     msg["To"] = "(my gmail address)"
     msg["Subject"] = "(a test subject)"
     msg.set_content("(a test body)")

     with smtplib.SMTP("127.0.0.1", 25, timeout=30) as smtp:
         smtp.send_message(msg)
     
     print("Message submitted successfully to local Postfix.")

and have it show up instantly in my gmail within seconds. This is powerful. (I've removed the details from this comment.)

I understand that as my server's reputation grows, it becomes very powerful to be able to email anyone without any intermediary except potential spam filters. I am very careful about what I put on my server.

Nevertheless, I had a recent experience that was a little sad for me. I wanted to forward some mail to my gmail address automatically, and used ChatGPT Sol 5.6 on medium thinking time to help me with the administration to do this. (I find extra high and pro thinking times are excessively long.)

I was very disappointed with the results, which included a very badly written regex for authentication. I'll write up my experience in an experience report. It was a big disappointment for me.

The burden on administrating one's own email is already very large, and it is disappointing that we can't really rely on frontier models to help with it.

bell-cot•about 3 hours ago
I see no upsides to a Google/Microsoft duopoly in email. Except for those already-far-too-powerful corporations.
thelastgallon•about 2 hours ago
We have to figure out a way to get out of FB social, iOS/Android phone, Google/Microsoft email, AWS/GOOG/MSFT cloud oligopolies. There is no competition and there will be massive rentier capitalism extraction from all these players for the rest of civilization.