Two experiments demonstrate how individual differences in working memory (WM) impact the strategies used to solve complex math problems and how consequential testing situations alter strategy use. In Experiment 1, individuals performed multistep math problems under low- or high-pressure conditions and reported their problem-solving strategies. Under low-pressure conditions, the higher individuals' WM, the more likely they were to use computationally demanding algorithms (vs. simpler shortcuts) to solve the problems, and the more accurate their math performance. Under high-pressure conditions, higher WM individuals used simpler (and less efficacious) problem-solving strategies, and their performance accuracy suffered. Experiment 2 turned the tables by using a math task for which a simpler strategy was optimal (produced accurate performance in few problem steps). Now, under low-pressure conditions, the lower individuals' WM, the better their performance (the more likely they relied on a simple, but accurate, problem strategy). And, under pressure, higher WM individuals performed optimally by using the simpler strategies lower WM individuals employed. WM availability influences how individuals approach math problems, with the nature of the task performed and the performance environment dictating skill success or failure.