I can't remember exactly which company it was, but most start-ups that have an "open core" model but also provide hosting have terrible, terrible set up guides (willfully in most cases).

Thankfully with the move to Docker, this is becoming less relevant if you are simply an end user, not a contributor.

By far the worst I ever experienced was ten years ago, in the final versions of Chrome that supported Java Applets, they had a massive list of ridiculous security and signing requirements to get a Java applet working for users. Took me weeks to get everything right from buying expensive certs from GoDaddy to writing the manifests and signing the .jars.

Me personally: I recently had a lot of issues trying to setup MemGPT. A lot of the commands have implicit assumptions about the kinds of setup / configuration already in place, and without such configurations, they fail in non-obvious ways. Even trying their Docker wasn't always successful. I eventually figured it out, but wasted hours I'd rather have back.

In the web and PHP world, the Drupal 7 to 8+ upgrade process. It's really more of a completely rewrite with close to zero code reuse, but the guides didn't make that very clear and the technical docs were just as bad. For such a big project, it was the worst documentation I've ever seen. I got a few weeks in before realizing, man, it's probably a good time to jump ship from Drupal altogether (we moved to Next.js instead) -- best technical decision I ever made as a dev. Not only was the migration much easier, the end result was much cleaner, and the hosting much cheaper, and the devs much easier to hire for.

And that was like half a decade ago, and the migration process has stayed so bad for so long for so many companies that the Drupal org kept delaying the v7 end of life. It was originally supposed to have died in 2021, then they pushed it back a year, then another year, and now it's been pushed back to 2025, but in the meantime third parties have made compatibility shims to run Drupal 7 on top of / within newer versions or something like that. I don't think it's ever going away at this point. There's an entire cottage industry, with their own conferences, around supporting old Drupals. The chaos of Drupal makes the Javascript ecosystem seem simple in comparison, and makes Wordpress look like the epitome of a well-managed project.

It was my first (and last) time working with Drupal. It's the only software I've ever used that I flat-out hated, and swore to never touch ever again. If someone offered me a million dollars a year to maintain a Drupal install, I'd instead pay them to never talk to me again. That migration scarred me for life.

nvidia drivers + cuda + tensorrt + deepstream + PyTorch = Madness

some setups that have given me pain (though some at age 16 so can't validate now):

- hot-reloading on xcode+swift / ios app dev in vscode

- dwm-style window management on macos that just works

- setting up arch linux (back in the day)

- de-bloating ubuntu (gnome2 ui mainly) without breaking it (back in the day)

- raspberry pi os used to hate all my usb sticks regardless of size or make

Prior to WSL and .net core.

Anything c#, .net, Microsoft.

So many GUI tools to accomplish what shouldve been a one line cli command.

Anything Microsoft related, Windows Server included.

Anything involving Oracle.