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Yeah, I find the back and forth with Claude is often better than trying to front load everything in a massive and detailed prompt.
The counter-intuitive nature of LLMs is so simultaneously interesting and frustrating. Overloading a single prompt definitely can create challenge remarkably similar to human short-term memory and attentional drift.

LLMs gain so much knowledge and capability from absorbing the symbolic relationships embedded in human language but in doing so, inevitably absorb many of the human foibles, sensitivities and weaknesses reflected in our languages.