Background: The cost of diabetes medications and supplies is rising, resulting in access challenges. This study assessed the prevalence of and factors predicting underground exchange activities—donating, trading, borrowing, and purchasing diabetes medications and supplies. Research Design and Methods: A convenience sample of people affected by diabetes was recruited online to complete a survey. Mixed method analysis was undertaken, including logistic regression to examine the relationship between self-reported difficulty purchasing diabetes medications and supplies and engagement in underground exchange activity. Thematic qualitative analysis was used to examine open-text responses. Results: Participants ( N = 159) self-reported engagement in underground exchange activities, including donating (56.6%), donation receiving (34.6%), trading (23.9%), purchasing (15.1%), and borrowing (22%). Such activity took place among a variety of individuals, including friends, family, coworkers, online acquaintances and strangers. Diabetes-specific financial stress predicted engagement in trading diabetes mediations or supplies (OR 6.3, 95% CI 2.2-18.5) and receiving donated medications or supplies (OR 2.8, 95% CI 1.1-7.2). One overarching theme, unmet needs, and three subthemes emerged: (1) factors influencing underground exchange activity, (2) perceived benefits of underground exchange activity, and (3) perceived consequences of underground exchange activity. Conclusion: Over half of the participants in this study engaged in underground exchange activities out of necessity. Providers must be aware about this underground exchange and inquire about safety and possible alternative resources. There is an urgent need to improve access to medications that are essential for life. Our study points to a failure in the US healthcare system since such underground exchanges may not be necessary if medications and supplies were accessible.