Not necessarily. A 500 response means internal server error and could be anything. Returning a 500 doesn't indicate any protections just that there was a server error. I guess that it returned anything would mean the server is still running but it takes time to delete everything
/./ would apply to the current directory, and /../ would move into the parent directory. I imagine the idea is to start in a deeply nested directory, /home/user/Documents/old and begin either maintaining the directory (in a sense doing something like '–0' or reverting to a more basal directory (alla '–1'). The branch moving into ~/Music/badSongs is probably a way of trying to disguise the intent of parsing /.././.././.././.. to root and then /* to glob all root directories.
I imagine if for some reason ChatGPT was running Zsh or something that supports that kind of augmented Bash syntax it would work, but realistically it likely would fail.
I think someone might have better luck by attempting to rm - rf --no-preserve-root with a series of random, less-necessary files and throw a /* in the mix. Or attack another important directory that might get overlooked like /proc/*
I'm sure you could make it more general by traversing through /usr/libs and back but I don't know the most common denominator for all Linux distributions and am too lazy to check.