Mailinabox's use of such an old OS is the exact reason I skipped it and went for Mailcow instead. It also placed very strange limitations on the stuff you could do with the system once it was set up and running according to the documentation, presumably to make sure the project maintainers had only a few types of configurations to support.

I have nothing against the concept of Mailinabox but when you create a "hands-off" project like that, your project should also include stable major version upgrades to LTS versions. From what I can tell, MIAB switched from 14.04 directly to 18.04 (skipping 16.04). Their goals and ideas are noble, but I don't think the project is very reliable if they skip major OS releases just like that (and are very late to the party when it comes to support for newer versions, releasing a version compatible with 18.04 only months before 14.04 support was dropped entirely).

I appreciate the enormous amount of work it takes to achieve something like this, but marketing your product as something "you don’t need to be a technology expert to set up" brings with it certain expectations (or even, responsibilities). Your issue with an outdated LE client should have never happened if the project had achieved its goals, for example.

A modern setup with MIAB based on Ubuntu 18.04 will have OS support until 2028, so the situation has improved; Ubuntu has switched to 10 years of support instead of 5.

> Essentially you are arguing that something like Mailinabox can not or should not exist because it falls somewhere between 'managed hosting' and something that can be set up for a few years in order to serve a purpose.

The problem is that software doesn't work like that, unfortunately. Bugs and security issues are found and need to be patched. Volunteers don't want to fix five years of releases of their software and for companies it doesn't make financial sense to do such work for free. A Windows server box with regular reboots for security updates will work fine for a bunch of years, but that guarantee is hard to make when your software runs on volunteers and occasional corporate sponsors.

> That's not a very encouraging future, maintaining basic internet infra such as mail, web and DNS servers should not be so hard that you can only do it if you want to pay third parties big bucks to do so.

There's a reason companies have been providing paid services for this since the dawn of the web. Hosting software on the internet isn't maintenance free and it never was. If you desire a setup that keeps working with minimum maintenance without the risks that come with volunteer work, you'll have to pick a stable OS (like Ubuntu or its competitors) and software stack from the LTS repositories and configure it. You can apt-upgrade anything from the official Debian repositories without reconfiguring anything. You can upgrade and It Just Works as long as you stick to the packages provided by the people maintaining your OS. This works until your OS reaches end-of-life, which is the next time you should do intensive system admin effort. Luckily, this is announced long beforehand, so you can plan accordingly.

This still means you'll run into trouble when (free) external parties decide to drop your OS because of the growing amount of software stacks and configurations they have to support over the years. However, if you practice running external stuff in a contained environment (with tools like Docker) you'll get to keep the best of both worlds for as long as possible. Alternatively, you can use setups that don't hide behind magical one-command-fixes-all setups, like manually entering certificates instead of relying on Some Cloud System to do it for you.

If all that is too much for you, which I can completely understand, then maybe running your own servers might not be for you. The premise of bringing self-hosted, federated services to the every-day consumer is nice, but I'm afraid it'll always be little more than a dream. The modern web is either part of the Cloud (TM) or a bunch of projects glued together by random chance and best effort; running your own stuff unfortunately requires either money to be paid or effort to be made.