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Why is self-hosting still this painful in 2026?

I tried to set up a clean self-hosted stack this weekend. It was a nightmare. Why is this still so painful in 2026?

4/19/2026 Elian Van Cutsem

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Why is self-hosting still this painful in 2026?

This weekend, I tried to set up a clean self-hosted stack.

Nothing crazy. Just a couple of services I wanted to run locally.

What I expected:

  • spin up a few containers
  • connect them
  • done

What actually happened:

  • Docker configs everywhere
  • random ports colliding
  • containers breaking for no reason

At some point I just stopped and thought:

why is this still so painful?

We have amazing tools.

We have Docker. We have open source everything.

And yet, setting up a simple stack still feels like:

  • reading docs for hours
  • debugging weird issues
  • copy-pasting configs you barely understand

It doesn’t feel like building.

It feels like maintenance.

And I think that’s the real problem.

Not the tools themselves.

But how fragmented everything is.

Every tool:

  • different setup
  • different conventions
  • different expectations

So nothing really fits together.


I don’t have a solution (yet).

But I’m starting to explore one.

More on that soon.

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