In ST:TNG 2:21 "Peak Performance," Data declares himself unfit for duty after losing a game of Strategema. He tells Dr. Pulaski regarding his loss:
This has indicated that I am--damaged, in some fashion. I must find the malfunction.
Eventually, Picard comes in and tells Data that not only is every decision not perfect, but:
It is possible to commit no mistakes and still lose. That is not weakness. That is life.
But Data is a Starfleet officer. He graduated Starfleet Academy. He encountered the Kobayashi Maru no-win scenario. He's familiar with the idea of making all the correct decisions and still losing--that's a fundamental principle that is taught to all cadets in the Academy. How did Data draw the conclusion that he is damaged, rather than the game being a no-win scenario, and why did Picard need to teach Data a lesson that he should have learned in the Academy?