A common practice among endurance athletes is to purposefully train in hot environments during a “heat stress camp.” However, combined exercise-heat stress poses threats to athlete well-being, and therefore, heat stress training has the potential to induce maladaptation. This case study describes the monitoring strategies used in a successful 3-week heat stress camp undertaken by 2 elite Ironman triathletes, namely resting heart rate variability, self-report well-being, and careful prescription of training based on previously collected physiological data. Despite the added heat stress, training volume very likely increased in both athletes, and training load very likely increased in one of the athletes, while resting heart rate variability and self-report well-being were maintained. There was also some evidence of favorable metabolic changes during routine laboratory testing following the camp. The authors therefore recommend that practitioners working with endurance athletes embarking on a heat stress training camp consider using the simple strategies employed in the present case study to reduce the risk of maladaptation and nonfunctional overreaching.