Achievements may not unlock until closing game or returning to main menu. "Know your stuff" may take a couple tries or only work in certain menu (don't remember which).
Losing on easy is not hard once you know how to win. To lose, don't land on extra turns, leave pieces open to capture, and block your own pieces. Winning on easy may be the fastest way to finish a game, unless you play online with a partner and one intentionally loses, but the game is pretty random and you can be forced into making a move.