[Bug] Claude repeatedly guesses instead of using lookup tools despite explicit instructions and prior context

Resolved 💬 3 comments Opened Apr 17, 2026 by drewdraft Closed Apr 20, 2026

Bug Description
no matter how many times i tell claude to not guess and look up answers before trying to navigate me around applications i don' tknow it always resorts to guessing. every single time. it has it in memory already. and eveyrtime i tell it that it failed it adds it to memory again. which i then have to tell it that it already did that so i then has to clean up it's memory. so it's wasting so many tokens!

Environment Info

  • Platform: darwin
  • Terminal: Apple_Terminal
  • Version: 2.1.107
  • Feedback ID: e9a928e9-2534-4183-9eb2-27e103423996

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