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

utcc.utoronto.ca

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

#281
post #197

Earlier quoted context omitted.

> Sending your mail yourself is the real hard part No, having quality spam and fraud filtering, and quality security, that you host yourself, is by far the much harder problem. I would argue that outsourcing your email to Proton or Tutanota is not running your own "artisanal" email server. By the way, even with those email providers, I still have terrible spam and fraud emails getting through filters that I never wou…

Well, on the flip side unless you constantly check your spam folder (which pretty much completely defeats the purpose of a spam filter) you most definitely have lost important mails thanks to gmail. I just don't see what people see in gmail part from the google brand - which surely isn't a good thing anymore.

I'm not here to be a Google apologist, but in the 10 or more years that I've used gmail, I don't think I've ever had an important email go to spam.

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

#282
post #122

I would really say that "running your own email" is a set of things that can be done independently: - Getting your own domain and using a provider such as fastmail or proton is a first step that gives you lots of security fom arbitrary. Because you own the doorstep, you can change provider without having to inform all your contacts of the move. You're also more secure from unilateral moves from your provider. -Hostin…

I think #1 is a super solid idea. I'd love to go beyond that— I'm familiar with the tech and love the satisfaction of a more DIY approach— but other end users preclude my doing so.

The author mentions quality in big email service but only passingly mentions what that encompasses. Smooth, responsive, well-worn, ceaselessly preened, and smoothed-over end-user UIs are important. Unfortunately, the open-source alternatives are comparatively rough.

(As a long-time developer and more recent designer, I write a lot of open-source code myself. I understand that these are complex and tedious problems to solve. However, without frank critique, "Open-Source Alternatives" will always be "Alternatives.")

Every interface I saw needed fundamental design work. My recent research showed 2+ decade old interface layouts w/new features just bolted on, visually complex toolbars, menus, and lists, little editing for views and controls, and comparatively unattractive designs(, which even if it doesn't matter to you, that doesn't invalidate its importance to others.) Even this crowd— people accustomed to configuring complex applications— lament the clunky interfaces.

To me, most open-source interfaces are like eating on a diet. Your sense of accomplishment offsets the discomfort... at least for a while. End-users, however, don't have or need, that holistic view of the service. To them, the interface IS the service. DIY/tech accomplishments are abstract and indirect factors, at most. For most, it's like eating on-diet, but someone else loses weight. Attractive alternatives make that unsustainable.

So the real hard part isn't technical— it's assembling an email stack where users don't feel deprived for having chosen it.

The solution is more collaboration between design and development expertise within the FOSS. If you have a position of authority in any FOSS projects, I implore you to be open-minded when presented with interface design ideas.

Happy to talk about productive ways to engage with designers and design feedback.

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

#283

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

Yup, between the message trace and just reading the headers I have not been wanting for visibility... and as the Exchange Online admin I've found that 99% of deliverability issues end up resting with the outside party failing to read their own infra's NDRs anyways.

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

#284

Earlier quoted context omitted.

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?

For Canadians, .ca seems a generally well behaved and managed TLD under community control.

EDIT: .ca is not particularly tech community related, but that doesn’t matter to me.

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

#285
post #242

Earlier quoted context omitted.

According to AWS, most mail servers will not even count statistics for low-volume senders. If that is true, then it won't matter whether your personal email server has been up for 20 years or 1 year, it won't have any reputation.

This matches my exprience. I switched recently after 10+ years, and was cautious that this might be a problem but it hasn't been at all. I think it has more to do with the choice of ISP.

I think they meant servers with no reputation are punished. Other comments said so at least.

What ISP should someone choose?

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

#286

Isn’t the fear getting your domain blacklisted? You’d never know unless somebody contacted you through alternate means to ask about lack of response.

It's obvious when your domain (well, the IP really) is blacklisted. You either get a nasty error from the mail system saying it didn't go through or that the server was unreachable or what have you. You're always going to get some notice that it failed. In that case I contact the recipient a different way and say, "hey, you're mail server is broken, can you please fix it?" Usually this means them contacting their mail provider and asking why they are blocking mail from someone they need to communicate with. If it's someone like Google, they'll realize they can't actually get any support and think twice about using Google for mail.

A lot of people will say, "no they'll blame you for it not going through", but that's rare. Most people will be receptive to your insistence that you're trying to send them mail but their provider is in the wrong.

Now, if you mean blacklisting in the sense that the server has shadowbanned you and is sending back "221 OK", then, again, you have an affirmative defense: "hey, you're mail server said it accepted the mail, can you please check with your provider on what they did with it?"

In either case, this is actually not a good thing for the recipient's mail provider especially if they pay for that provider. "Why did you accept the email from the sender but not put it in my mailbox? Who else have you done that for? Why am I using you as my mail provider again?"

I have a circle of influence... about 100 people. All 100 of those people would switch mail providers if I asked them to. And I think a lot of people have a circle of influence around this size as well. So there actually is an amount of control over these bigger mail providers. They will be receptive to "I just told your customer to switch because you won't let me email them" especially if it's widespread. In exchange for that "power", I make sure my mail server is as clean as possible and quickly respond to any notices sent to my abuse@ address.

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

#287

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,…

> Things that have happened in the last 20 years include SPF, DKIM, DMARC

Right, of course. The protocols are more complex. (Add TLS, MTA-STS...) But whereas 20 years ago you _had_ to start from scratch and understand the whole stack, today that's just not necessary. There are numerous projects that make running a mail server readily possible without knowing e.g. the sendmail configuration macro language. And there are many many more good resources to learn it all if you want to know than there were 20 years ago. It is both a more complex technology and also undeniably easier for people to actually do it.

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

#288
post #130

Earlier quoted context omitted.

There’s a midpoint at #1.5 where you control the domain and rely on an external host, but also have a continuous archive of your historical mails on your own server. Otherwise with a standard IMAP setup, if your provider locks you out, you’re limited to only the most recent N messages on connected devices.

Buy a domain for $20, get a GSuite account with it for $6 a month or similar, then archive all your mail via Outlook or your desktop email app of choice. You also get a lot of other tools and storage space for very low cost which I find useful. It's still using Google but it allows plenty of control and management, and I can take my domain anywhere with minimal stress. It's a decent compromise.

Just make sure that you use a different domain registrar than Google Domains, and make sure your admin email address is not gmail. Because if Google bans your account, you will be totally screwed.

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

#289

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.

My mail server running on DigitalOcean has been relatively trouble free over the last 9 years. It runs docker-mailserver and is used by me and a dozen employees of my various small businesses. It requires some effort to maintain and understand, and I’ve had a few deliverability issues over the years but they are generally with niche providers. I’ve never had trouble sending mail to the big providers. Every time I rea…

I think DO is really good about policing their IP space. When I signed up for the Microsoft JMRP [0], DO was already a contact of record for the IP I was using. I just appended myself to the list to get any abuse reports as well.

>Every time I read comments about the impracticality of self-hosted email, I scratch my head. Maybe I’ve just been lucky.

I feel the same. I've had one or two hiccups but smooth sailing for the most part. I'm also happy to provide receipts that show how the recipient's mail server is responding when I send the emails. It's a powerful tool to say, "your mail provider is misbehaving, look!" They will wonder how many people tried to send them email that didn't get to them.

[0]: https://postmaster.live.com/snds/JMRP.aspx

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

#290
As far as spam filters go, too many good emails end up in spam folder nowadays. It has become a common place - "check you spam folder". I find it's easier to have a few manual filters and just delete all the remaining spam manually as it arrives, because the alternative is to check two folders every time - Inbox and Spam folder, with all the spam still there of course.
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