As distance programs grow and online learning flourishes, a variety of learners are attracted to the prospect of this educational approach. Emerging issues for institutions include the ability to support and work within a diverse and multigenerational group of learners in the classroom. Familiarity with the pertinent issues and challenges of adult and multi-generational learners is approached in the context of understanding differences in values, outlook, and expectations. Further inquiries into the support systems institutions need to address are explored in addition to the legal and ethical implications to programs. Finally, further suggestions for curriculum development that taps into promoting learners while avoiding conflicts is shared for instructors of online learning to readily implement into their pedagogical methodology.