Local barbershops, often racialized safe spaces, have long been used as sites of health interventions targeting Black American men. Here, we present findings from a barbershop intervention held in the Southeast where Black men were (1) approached using recruitment strategies informed by a community advisory board, (2) screened for type 2 diabetes, and interviewed to understand their levels of medical trust, motivation for testing in the barbershop, as well as the utility of barbershops in health promotion programming. The community advisory board consisted of five Black men from the city understudy. The intervention sample included 27 participants: 20 males and 7 females. Several men insisted on testing after their female spouses and two local women approached testers and were not denied access to screening. Themes that emerged for medical trust ranged from yes to no. Themes that emerged for motivation to screen included to know status (codes: for self, for loved ones), financial motivation (codes: free testing, incentives), risk (codes: family, race specific), referral (codes: other community member, barbershop), and convenience. Themes that emerged for the utility of barbershops in health interventions included access to people, trustworthy setting, location, and yes, they are useful with no explanation. Results show that barbershop interventions make a dynamic way to engage community members who otherwise may not trust medicine as a social structure. Results also show that future scholars and interventionists should consider gender dynamics, social class, and engaging community members as best practices in engaging Black men.