Asynchronous discussions are typically considered an essential aspect of online case-based learning. While instructors implement discussions to support a variety of instructional purposes during case-based learning (e.g., facilitate students' sense making, prompt the consideration of diverse perspectives, debate complex topics), whether students receive the expected benefits is unclear, and little research has considered how students intentionally participate in discussions to support their learning during case-based learning. At the same time, students' participation in asynchronous online discussions represents a complex endeavor. That is, students must make several decisions regarding how to effectively participate, while simultaneously experiencing several challenges. The purpose of this exploratory multiple-case study was to consider the experiences of six graduate students participating in asynchronous online discussions as a part of a case-based course. By analyzing these experiences, we were able to conceptualize students' navigation of an asynchronous online discussion as a problem-solving process and consider individual problem-solving approaches. Results indicate that students relied primarily on instructors to determine the purpose of their discussion participation, expressed differing levels of value for participating in discussions, adopted a variety of strategies to meet discussion participation goals, and assessed their participation efforts mainly based on guidelines set by the instructor. We offer suggestions for effectively designing and facilitating asynchronous online discussions and discuss areas needing future research.