We present CADament, a gamified multiplayer tutorial system for learning AutoCAD. Compared with existing gamified software tutorial systems, CADament generates engaging learning experience through competitions. We investigated two variations of our game, where over-the-shoulder learning was simulated by providing viewports into other player’s screens. We propose a novel lab study methodology where participants compete with one another, and we study learning transfer effects by tracking the migration of strategies between players during the study session. .Our study shows that CADament has an advantage over pre-authored tutorials for improving learners’ performance, increasing motivation, and stimulating knowledge transfer.