<p>Good luck Debate Mom! It took months to be sure that boarding school had been a good choice for my daughter, though the time course of her discontent was more like Tapper’s, and therefore easier for me as a parent than what you describe. I know a student who was perhaps more like your son: desperately homesick initially, requiring intervention from the counseling office, much attention from prefects and advisors. He ended up being the most happy, enthusiastic and successful student you could imagine (though the adjustment wasn’t instantaneous). You and the school are doing all the right things, so hang in there! Hopefully things will improve soon.</p>