As the need for qualified medical and allied health professions has grown, so too have the natural feeder undergraduate programs of kinesiology across the country. With an impending “enrollment cliff,” it is necessary to assess the needs of our students and be proactive in addressing curricular issues, initiatives, internship opportunities, and academic advising support. The purpose of this article is to highlight formal and informal data collection strategies and suggest solutions to undergraduate issues that pertain to retention and success. Data from current students and alumni shed light on issues that plague kinesiology programs and present unique challenges to students as they attempt to pursue careers in the medical and allied health fields. Two R1 kinesiology programs identified similarly themed issues using informal and formal data collection approaches. Those themes were undergraduate major identification, career options, curricular issues, financial concern, and emotional fortitude. Suggested solutions and current best practices are provided to address the common themes that hold our undergraduates back from achieving their career goals.