One of my most vivid memories of a poor experience with an LLM was trying to get the web version of GPT 5.3 or 5.2 to help me figure out why I was unable to register for a tournament on start.gg
After trying several things it became apparent that the behavior could only be explained as the result of a bug with the start.gg site, chatgpt refused to consider that it could be anything other than user error on my part, despite the failure I was seeing making no logical sense.
Eventually I opened the firefox dev tools and noticed that the post request parameters to complete the registration were being incorrectly filled out and realized it was because of the metadata in the url that came from clicking the complete registration link I was emailed. Removing the url paramater added by the email link fixed the issue.
There was roughly a 0% chance that the LLM was going to trust me enough to consider it was a real bug.