The Prisoner/Recap/E09 Checkmate

Quoting Wikipedia:

Number Six is persuaded to participate, as the white queen's pawn, in an oversized game of chess using people as pieces. A rebellious rook (Number Fifty-eight) is taken to the hospital for "evaluation". After the game is completed, Number Six talks with the Chess Master (Number Fourteen), who comments that one can tell who is a prisoner and who a guardian "[B]y their disposition. By the moves they make."

Number Six is later invited to visit the hospital to observe the fate of Number Fifty-eight (the rook), and sees him subjected to Pavlovian mind control treatment. The woman playing the queen (Number Eight), who had fraternised with Number Six during the game, is subjected to hypnosis to make her fall in love with him and report his whereabouts should he attempt to escape again. Number Six shuns her, but seeks an alliance with Number Fifty-eight and other villagers that he now believes he can identify as prisoners, not guardians.

They attempt an escape by making a two-way radio out of various pilfered electronic parts and then hailing a passing ship with a Mayday distress call, pretending to be a crashing airliner. Number Six discovers, however, that again he has been a pawn – Number Fifty-eight had mistaken the strong-minded Number Six for a guardian. Believing that the escape attempt was a test of his loyalty, he reported it all to Number Two.