Nonfunctionality of Chats Due to Excessive Content

I maintain chats by subject and sometimes they get quite long. I have had some data processing errors recently and when I started a new chat, these issues did not happen. It seems that if the length of a chat is too long, this impacts the quality of the data processing. Can anyone confirm this is true and also whether its necessary to establish a new chat with every inquiry? Is there a way to identify when a chat is overloaded? Would be helpful for instance, if the program could report this condition when it is repeatedly unable to resolve obvious errors after feedback is provided.