What is going on with Claude? Am I doing it wrong?

I’ve been using Claude since about March for a few non work related purposes, two medical chats are the longest ones, particularly one about my dogs health. The rest is completely casual and basic, not for therapy or general discussion, just usefulness or intellectual curiosity. I’ve always just started chats within whatever version it defaults to without changing anything. I started on the free version then upgraded to Pro when the medical chats got a bit more in depth and memory, detail and context became