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Running your own email is increasingly an artisanal choice, not a practical one

utcc.utoronto.ca

251–260 of 519 posts

Re: Running your own email is increasingly an artisanal choice, not a practical one

#251
post #20

> … general security will not be as good as they have. > Entirely "on premise" email is now an inferior thing for almost everyone. I disagree on this one. Placing your email with a big player means that by definition, they have access to your mailbox (with sensitive stuff hopefully encrypted). To allow that you have to trust the big player and the countries where they reside. They can drop you any time for political…

Most people have no idea that email is not secure.

Re: Running your own email is increasingly an artisanal choice, not a practical one

#252
The comments all seem to be from people who think making an artisanal choice is a bad thing. There should be more art, experimentation, and expression in computing. If we've outgrown running our own mail servers as a practical choice, because there are now more good options, and we can enjoy running a mail server as a more humanly choice, that's a good thing.

Not much has actually changed about the complexity of running a mail server in the last 20 years --- if anything it's gotten easier. What's changed is there are other, polished, turn-key options now. Great. (Those options tend to have spam policies that aren't friendly to the independent servers, but that's life.)

Choose to be artisanal.

(I'm the primary maintainer of https://mailinabox.email/.)

Re: Running your own email is increasingly an artisanal choice, not a practical one

#253
It's amazing how quickly people with strong feelings about email come out when any mention of self hosting is made.

They can't prove a negative, but they valiantly try, often using the very points that are excellent reasons to self-host as reasons we should all just give up.

"It doesn't work for me, so it won't work for you" is rather weak when the reasons aren't articulated, when generalizations are made without detail, when hardly any attempt at all was made to find the root of the problem. Your failure is not the same as my quarter century of success.

They also tries to make everything all or nothing, which plainly lacks any imagination. I wouldn't want an admin on my staff who tries something, then gives up at the littlest of hurdles.

There are plenty of issues, but there are also plenty of solutions. You're having issues sending because your netblock sucks and you don't have money for something better? Pay a few dollars to smarthost, for instance.

With Google and Outlook, you get no determinism, no accessible logging, no clear view about their filtering rules, no assurance that your outgoing email won't get blocked, anyway, because of the tremendous amounts of spam these monopolies allow...

We should encourage MORE people to self-host email, not less. We should never just assume the monopolies are the best we can do.

Re: Running your own email is increasingly an artisanal choice, not a practical one

#254

Earlier quoted context omitted.

But what if... the TLD owner decides to 10x the domain price?

As someone who de-googled about 5 years ago by buying a nice three letter .io address this hits right in the feels. I could go through the process again (not fun) with some ridiculously long .com/.net or other OG tld which are probably somewhat more resistant to rent seeking practices like this or I just suck it up and hope it remains pricey but not egregious.

Are there any truly "community-owned" TLDs for the tech community? Would such a thing be possible and/or useful?

Re: Running your own email is increasingly an artisanal choice, not a practical one

#255
post #41

I do away with the middle ground. I rent email services from businesses that specialize in email hosting and I own domain name. No way I will have my email serviced by Google / MS / Apple and the likes.

Who do you use? After seeing all the horror stories posted on HN, I have been worried about getting banned from $MegaCorp randomly and would like to minimize the blast radius if that were to happen.

I'm using mailbox.org (1€/month) for my domain and I have nothing but praise so far.

Re: Running your own email is increasingly an artisanal choice, not a practical one

#256

Earlier quoted context omitted.

> If you put some decent effort [...] it works Well, I put in more than some decent effort, and I didn't get it "to work". I detailed my efforts here: https://www.attejuvonen.fi/dont-send-email-from-your-own-ser... Please stop spreading falsehoods. If you were able to somehow get your own email server to deliver email to Gmail and Outlook, great, good for you - but stop pretending that anybody can do it.

Lots of sister comments here saying that they've been running a mail server for X amount of years, where X is a rather large number. That will obviously come with some reputation for your mail server, reducing the curve of being classified as down. I would be interested in hearing from someone who tried to setup a new mail server in the last 1-2 years who was able to run it without a hitch.

In my case x>10y for a personal server, but that reputation got ruined when some test email account I had created with a weak password and forgotten, got breached and some spammers started sending spam. My mail server (smartermail) notified me within an hour of the abnormal number of emails and I disabled the account immediately. But that was it for the reputation of that IP. Fortunately I could switch to a spare, clean IP.

That being said, now I monitor and auto-ban failed authentication attempts to smtp/imap (among others) and running the service is fairly low maintenance.

But the morale of the story is that you are only one weak password from one of your users away from your mail server getting blacklisted as a spam server. So while I think it is fairly easy to run a personal server, running one for a small organisation is another matter.

Re: Running your own email is increasingly an artisanal choice, not a practical one

#257

It's amazing how quickly people with strong feelings about email come out when any mention of self hosting is made. They can't prove a negative, but they valiantly try, often using the very points that are excellent reasons to self-host as reasons we should all just give up. "It doesn't work for me, so it won't work for you" is rather weak when the reasons aren't articulated, when generalizations are made without det…

You get access to logging etc. with an outlook business account

Re: Running your own email is increasingly an artisanal choice, not a practical one

#258
post #37

Earlier quoted context omitted.

> " simply awful. No IMAP or POP " Microsoft seem to disagree with you there: https://support.microsoft.com/en-us/office/pop-imap-and-smtp...

As I mention in my post, this is the setting our admins chose so I do not blame MS for this (they support both, I know). Another setting they chose is to delete emails over six months of age and there is nothing I can do about it either. The search and the interface are entirely the fault of MS as are the lack of more subtle features such as mass emails (which I have to use often while teaching online).

I read as "(No IMAP or POP) and (No forwarding which is University policy)".

Mass emails via distribution lists are a thing - https://www.wisestamp.com/blog/managing-distribution-lists-i...

As is sharing links to OneDrive content with a password on it: https://support.microsoft.com/en-us/office/share-onedrive-fi... ("Set password: lets you set a password to access the file. When a user clicks the link, they will be prompted to enter a password before they can access the file. You'll need to provide this password separately to anyone you want to share the file with.")

(Poor quality sluggish Outlook client, dropping important emails into Spam, not being as configurable as a custom mailserver, hit-or-miss search results, those are all things I can agree with, I'm not just defending it).

Re: Running your own email is increasingly an artisanal choice, not a practical one

#259
post #230

Earlier quoted context omitted.

Internet was meant to be decentralized. Lets leave it this way. I am running my server for 15 years and couldn't be more happy with "artisan" infrastructure. I don't want or use webmail (sluggish), I don't want others fingerpoking my emails, I don't want various compulsory registration systems (like requiring my phone number out of """security""" reasons like google), giving others the ability to kill my account and…

Honest and non-rhetorical question here: Have any of your customers had an e-mail they've tried to send not arrive because the recipient's system was using a black-hole list that, for some erroneous reason, had you blocked? If so, were you able to successfully communicate with and/or reasonably work through whatever issue got you black-holed? I haven't administered e-mail servers for 20 years, but back when I did, th…

(Running a email system for a few thousand users)

> If so, were you able to successfully communicate with and/or reasonably work through whatever issue got you black-holed?

Yes. Practically all black-lists have a de-list form that one can use, and most seem to auto-delist fairly fast as soon they don't get any more reports from honey-trap and other sources.

We do have a few custom written ways to detect hacked accounts, and we don't allow users to set their own passwords. We also tend to discourage/deny users who do newsletters and other "higher risk" form of email. All emails sent by websites is sent through different servers, which also mean that a hacked website does not impact the reputation of the email servers.

Events with black lists maybe occur once a year and as I mentioned above, fixed fairly fast. One good tip is to keep an automated eye on the mail queue and react quickly when things start to look wrong.

Re: Running your own email is increasingly an artisanal choice, not a practical one

#260

The comments all seem to be from people who think making an artisanal choice is a bad thing. There should be more art, experimentation, and expression in computing. If we've outgrown running our own mail servers as a practical choice, because there are now more good options, and we can enjoy running a mail server as a more humanly choice, that's a good thing. Not much has actually changed about the complexity of runn…

I don't think artisanal is necessarily "bad", but we should all acknowledge that it will be more work for a result that's maybe better but probably worse for most people.

I ran my own mail server for 20+ years, finally giving up a couple years ago. I strongly disagree that it has gotten easier. As the article makes clear, it's a much more complicated world. Things that have happened in the last 20 years include SPF, DKIM, DMARC, and the rise of providers like GMail. And if you really care about owning your bits, in some ways colocating hardware has gotten harder now that VMs are hugely dominant.

The new requirements to be a good mail server are significant work to understand and implement. The feedback loops are also poor: it's hard to know whether you really have them right.

But the real killer for me was opaque major providers like Google. Occasionally, they decided they didn't like my little mail server. I and a number of other sysadmins couldn't find anything wrong with my setup. But mail wouldn't arrive. I even had SRE friends inside Google and they couldn't find out anything; apparently the GMail folks are very secretive.

There are only so many missed business opportunities and disrupted personal relationships I was willing to put up with for my personal taste for running my own servers. Eventually I hit that limit and switched everything over to Fastmail. For me personally, it was a great decision. It's cheaper and more reliable, and never again will I have to get up in the middle of the night to go to a colo. In contrast to my spending a few hours here and there, they have a whole full-time staff sweating deliverability. It's great!

If people think running a mail server is fun, I say go for it. But even there I'd strongly urge them to consider whether "this looks fun" is the right spirit to bring to anything important to their lives, and whether it will stay fun when it breaks at the least convenient time. So maybe keep it fun by using it only for things that don't really matter to you.

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