The worksite food environment, including vending options, has been explored as an important contributor to dietary decisions made every day. The current study describes the vending environment, and efforts to change it, in four Iowa worksites using a series of case studies. Data were gathered by local coordinators as part of the Iowa Community Transformation Grant project. Data were collected from three sources. First, the Nutrition Environment Measures Survey-Vending was used to assess healthy vending options in worksite machines before and after the intervention. Second, employee vending behavior was evaluated with a pre-, post-intervention survey. Items assessed attitudes and behaviors regarding vending, plus awareness and reaction to intervention activities. Third, program coordinators documented vending machine intervention strategies used, such as social marketing materials and product labels. The Nutrition Environment Measures Survey-Vending documented that the majority of vending options did not meet criteria for healthfulness. The vending survey found that employees were generally satisfied with the healthier items offered. Some differences were noted over time at the four worksites related to employee behavior and attitudes concerning healthy options. There were also differences in intervention implementation and the extent of changes made by vending companies. Overall, findings demonstrate that a large percentage of employees are constrained in their ability to access healthy foods due to limited worksite vending options. There also remain challenges to making changes in this environment. Findings have implications for public health practitioners to consider when designing healthy vending interventions in worksites.