The moment I almost cancelled my Max subscription

I've been using Claude intensively for knowledge work for months. Project setup, context blocks, structured prompts -  I put real effort into making it work well.

And mostly it does. But there's a pattern I kept hitting that nearly broke me.

When a session gets long and you're approaching the token limit, the quality degrades noticeably. Responses get shorter, less precise, sometimes contradictory to things established earlier. That part I understood.

What frustrated me more was that Claude would never say: "we're close to the limit, let's pause and carry what matters into a new session." It would just continue. Confidently. Producing worse and worse output while I kept going, not realising the session had quietly stopped working.

I had a task fail three days in a row. Each time, a fresh "yes I'll handle this" from Claude.ai and then the same drift. The context was there. The credits were there. Something else was missing.

I'm still here on Max. I figured out workarounds. But I think the more interesting question is why it took me so long to realise the session was the problem, not the prompt.

Anyone else hit this? How do you know when to stop and restart?