Student demand for online learning is at an all-time high, making the identification of practical strategies for supporting student success in online learning more vital than ever. Positive emotion has been shown to promote self-regulated learning (SRL) and engagement, both evidenced predictors of student success. However, little is known about designing online learning environments to elicit positive emotion in students. The purpose of this study was to assess the influence of play-infused learning design on SRL and engagement in an online, higher education classroom. This study is based on the premise that play is a positive affect emotional system that stimulates approach behaviors for the purpose of broadening an individual's thought-action repertoire, thereby preparing them to build intellectual and social resources that contribute to their ability to survive future challenges. The study used a mixed-methods approach to add to the current understanding of the ability of play, when it is designed into the higher education learning environment, to influence student engagement and SRL. In addition to three student surveys, data generated during normal course activities, primarily in the form of recorded student reflections, were analyzed using the systematic text condensation method. The thematic analysis provides insight into how play in the online environment resulted in student perceptions of enjoyment, fun, happiness, lowered stress levels, and social connection. These elements are discussed in relation to enhanced student engagement and SRL. The results of the study provide initial evidence that it is both possible and desirable to leverage the power of play in the design of higher education online learning environments to support student success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]