The university instructor experience around leading a course learning experience that includes multigenerational students with different levels of subject matter knowledge and understanding, as well as different levels of life experience, is the focus of this qualitative multiple case study. In addition to the university instructor participants, a student participant was also engaged in the study. The relational, international differences, similarities, conflicts, and strengths, as reflected through the participant interview reflections, resulted in discussions focused upon the primary themes of course design, course engagement, instructor collaboration, instructor community in-course efforts, assessment considerations, instructor-sustained emotional engagement or support, the journey through differentiated instructional efforts that may be impacted by generations intermixing within the course learning environment, as well as the potential generational differences and similarities between the university instructor and the course learners.