Since the introduction of the American Academy of Pediatrics Back to Sleep Campaign infants have not met the recommendation to “incorporate supervised, awake “prone play” in their infant’s daily routine to support motor development and minimize the risk of plagiocephaly”. Interventions are needed to increase infants’ tolerance for prone position and prone playtime to reduce the risk of plagiocephaly and motor delays. Associative learning is the ability to understand causal relationship between events. Operant conditioning is a form of associative learning that occurs by associating a behavior with positive or negative consequences. Operant conditions has been utilized to encourage behaviors such as kicking, reaching and sucking in infants by associating these behaviors with positive reinforcement. This dissertation is a compilation of three papers that each represent a study used to investigate a potential play based interventions to encourage prone motor skills in infants. The first paper describes a series of experiment used to develop the Prone Play Activity Center (PPAC) and experimental protocols used in the other studies. The purpose of the second study was to determine the feasibility of a clinical trial comparing usual care (low tech) to a high-tech intervention based on the principles of operant conditioning to increase tolerance for prone and improve prone motor skills. Ten infants participated in the study where parents of infants in the high tech intervention group (n=5) used the PPAC for 3 weeks to practice prone play. Findings from this study suggested the proposed intervention is feasible with some modifications for a future large-scale clinical trial. The purpose of the third study evaluated the ability of 3-6 months old infants to demonstrate AL in prone and remember the association learned a day later. Findings from this study suggested that a majority of infants demonstrated AL in prone with poor retention of the association, 24 hours later. Taken together these 3 papers provide preliminary evidence that a clinical trial of an intervention is feasible and that associative learning could be used to reinforce specific prone motor behaviors in the majority of infants.