Your human context also needs compacting at some point. After hours of working with an LLM, your prompts tend to become less detailed, you tend to trust the LLM more, and it's easier to go down a solution that is not necessarily the best one. It becomes more of a brute forcing LLM assisted "solve this issue flow". What's funny is that it sometimes feels that the LLM itself is exhausted as well as the human and then the context compacting makes it even worse.
It's like with regular non-llm assisted coding. Sometimes you gotta sleep on it and make a new /plan with a fresh direction.