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Very well observed. I found one more thing: they fail to consider what a 3rd person might understand from your conversation, so when you ask it to dump stuff into a Documentation, they keep making references to facts you had previously discussed or to the train of thought, completely irrelevant to bystander.

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100% -- this is the worst. Referencing all sorts of "words with made up contextual/analogous meanings" based on the conversation...outside of the conversation.

Does anyone have a read on if this is primarily a Claude issue, or if all LLMs do this?

I think it's fundamentally and issue with LLMs, for this to not happen they'd have to constantly think "what does other person think right now/what's their state of knowledge" AND also apply that to am additional, third person which would be reading the Docs. They can't even do the first bit well. I think it's a limitation we'll have to live with.

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