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I know the reason, I just took the opportunity of answering to a claude dev to point out why it's no panacea and how this requires consistent context management.

Real semi-productive workflow is really a "write plans in markdowns -> new chat -> implement few things -> update plans -> new chat, etc".

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That explains why it happens, but doesn't really help with the problem. The expectation I have as a pretty naive user, is that what is in the .md file should be permanently in the context. It's good to understand why this is not the case, but it's unintuitive and can lead to frustration. It's bad UX, if you ask me.

I'm sure there are workarounds such as resetting the context, but the point is that god UX would mean such tricks are not needed.

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Yeah the current best approach to aggressively compact and recreate context by starting fresh. It’s awkward and I wish I didn’t have to.
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I'm surprised this hasn't been been automated yet but I'm pretty naive to the space - the problem of "when?"/"how often?" seems like a fun one to chew on
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I think Gemini 3 pro (high) in Antigravity does something like that because I can keep asking for different changes in the same chat without needing to create a new session.
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It’s not that it’s not in the context, it’s that it was injected so far back that it is deemed not so important when determining the next token.
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