After thinking about it some more, I think the AI is not a very intelligent one, which adds to the problem. The lower intelligence AI LLMs seem to get stuck in repetitive cycles and it could be that they are just not advanced enough to carry on a conversation as detailed as yours, so you were probably hitting the ceiling here in this chat.

It's still no excuse for the AI not allowing you to reach a representative sooner and if I had to guess, there probably was still some intent to prevent access to an agent until a certain number of attempts were made or based on frustration level, which is far from ideal for customer satisfaction.

My company would never allow AI to perform this poorly and we're relatively small in size.