Quite a few have, the issue is that every Jira instance is a fractal shit snowflake of custom properties several layers deep through old failed migrations to new organization strategies.

And many times the API can do stuff that the UI doesn't allow, and everyone's relying on the UI to drive things, so you end up in weirdly broken corners because you didn't notice that you need custom_field_5537 to be paired with custom_field_442 or it doesn't appear on anyone else's dashboard. Also it claims custom_field_10995 is an integer type field, and returns as integers in the XML, but there's a pile of undocumented magic constant strings that you have to use instead when creating (but not updating!) a task or you get useless error messages. The web UI doesn't do this though (it's just integers in html and the request), and only 80% of the strings match the display text in the dropdown.

Automating Jira is the absolute worst programming experience I've ever had. I can completely believe that simpler setups exist and they're probably quite easy, but omfg.

Sadly it's still completely worth the effort. Highly recommended.

A dysfunctional organization will project its failures to everything it touches. I personally have not seen such mess, likely because working in regulated industries means there‘s usually some SOP or work instruction that is regularly updated, so the setup is driven by the compliance process. Nowadays, I opt in for Atlassian because it works fine out of the box, I avoid heavy customization (which would mean tool lock-in), and Claude can move the tickets itself anyway - no scripting required.

A colleague of mine said it even better, its like an old blanket filled with patches, small fixes and workarounds, so much that no one even remembers to how the patching was done ages ago!

Simpler setup is perhaps - have a the pm-informed list of req of what your teams' needs and habits, and implement from scratch. Perhaps would take less than customizing JIRA. With history and all.

Yeah I had the exact same experience. What values does `custom_field_836` need when creating an issue? It seems to be required in the API but not in the UI, and feeding a value returned from an existing issue doesn't work!

It's the API equivalent of formatting a document in MS Word.

I just had a thought: is there some API so obscenely baroque and painful to use that even AIs would flatly refuse to work with them?

It would be an interesting exercise to keep feeding a coding agent ever crazier interface designs until it cracks.

“The base64 of the rot13 encrypted EBCDIC string has to be included in a JSON in the XML SOAP request, but both the JSON and XML escaping is manual and incorrect...”

"...but first split the string into chunks no bigger than 64 bytes and spread the request amongst HTTP headers instead of the POST body. Reassemble by trying every possible ordering until one passes the decoding steps."

> Quite a few have, the issue is that every Jira instance is a fractal shit snowflake of custom properties several layers deep through old failed migrations to new organization strategies.

This is key, Jira is fantastic so long as you have an angry commissar enforcing discipline, otherwise its a total free for all wasteland.

I am not using JIRA anymore but I guess in 2026 you could write AI wrapper around clicking on UI elements?