I've found compactation kills the whole thing. Important debug steps completely missing and the AI loops back round thinking it's found a solution when we've already done that step.
For me, Claude was like that until about 2m ago. Now it rarely gets dumb after compaction like it did before.
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I find it useful to make Claude track the debugging session with a markdown file. It’s like a persistent memory for a long session over many context windows.
Or make a subagent do the debugging and let the main agent orchestrate it over many subagent sessions.