In honor of Jim Greer, we share our recent work--a design and development study of various learning supports embedded within the game "Physics Playground." This 2-dimensional computer game is designed to help students learn Newtonian physics and uses stealth assessment to measure, in real-time, their physics understanding. The game operates according to Newtonian mechanics where students draw simple machines (e.g., ramps, levers, pendulums, and springboards), or adjust sliders to manipulate physics parameters to solve problems. Over the past three years, a team of experts in measurement, assessment, learning sciences, game design, and physics education has iteratively examined how to enhance students' learning during gameplay. We incorporated supports for both physics understanding and game mechanics. Some of our designs showed promise while others did not and were discarded. Through three usability studies and a final learning study, we document the design, development, and testing of the final set of supports that involve modeling (Worked Examples, Physics Videos), modality (Animations, Formulas, Definitions, Hewitt Videos), and advice (Hints). We conclude with a discussion of the impact of incorporating learning supports, students' perceptions of the learning supports, and the lessons learned through our iterative process. Jim shared our passion for supporting student learning and we hope that by sharing our journey we spur others on to continue the work he loved. [This is the online issue of an article published in "International Journal of Artificial Intelligence in Education."]