Purpose: Diabetes is reaching epidemic proportions in the United States and African Americans are at greater risk than most. Disparities in the incidence of diabetes place African American women at a much higher risk than their white counterparts. As such, the purpose of this study was to evaluate a community-based educational intervention program aimed at changing diabetes attitudes, knowledge, and screening behaviors of African American women via cosmetologists trained as community health educators. Methods: Twenty African American cosmetologists joined the Black Cosmetologist Promoting Health Program. Their salons were randomized to disseminate diabetes or breast cancer information and given educational materials to display in their salons and give to their clients. Their clients (n = 984 women) consented to help evaluate the program, completing a baseline and 6-month follow-up survey regarding their knowledge, attitudes, and behaviors related to diabetes and breast cancer. Results: At the 6-month follow-up, self-reported knowledge about diabetes increased across both groups. However, despite similar programmatic structure offered to the two groups, there were no significant differences in diabetes knowledge, attitudes, and screening at follow-up. Conclusion: This non-significant outcome contrasted with the positive outcomes achieved by the parallel breast cancer program. Gladwell’s Tipping Point theory could explain the different outcomes. The programs differed in message content, messaging tone, and the environment in which the messages were delivered. The diabetes program lacked a clear, memorable, and upbeat call-to-action and an environment that socially and financially supported the uptake of the recommended actions.