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Innovation competitions and programs (ICPs) are acknowledged in existing literature as effective mechanisms for fostering innovation and entrepreneurship within universities, corporations, and beyond. These ICPs (including hackathons, design challenges, pitch competitions, and others) allow student participants to expand on the knowledge gained in their classes, grow their creativity, build an innovative mindset, learn from trial and error, and improve their collaborative skills in team settings. However, with these programs also come various obstacles that have the potential to negatively impact the overall student experience. These challenges can relate to funding, organization, team dynamics, outreach, accommodation, and more, impacting how these students perceive the impacts or benefits of ICPs. This paper considers the challenges and negative experiences students have faced while participating in ICPs based on past experiences collected from student interviews. Analyzing both reported challenges and negative experiences of students provides a guide to address concerns when developing future ICPs. Understanding the type of obstacles students face in these events may be the first step in making the necessary interventions for further improving the experiences of future participants and ensuring that ICPs add value to students across majors.