This study was designed to determine the effect of contextualized advisement and competition on transfer of mathematics skills in a computer-based simulation game in which participants helped their “aunt and uncle” fix up a house. Contextualized advisement referred to whether the participant had access to video-based advisement delivered by the aunt and uncle about how to solve the problem, and competition referred to whether or not the participant was playing against a computer character. A total of 123 seventh-and eighth-grade students were randomly assigned to one of five conditions formed by crossing the two independent variables and adding a control group. Results indicated an interaction between competition and contextualized advisement. Participants in the noncompetitive condition had higher transfer scores when they had access to contextualized advisement, while participants in the competitive condition had higher transfer scores when they had no access to contextualized advisement.