Although connecting youth with disabilities with early work experiences has emerged as a recommended practice in transition education, little is known about the extent to which the summer months might offer a meaningful context for providing such experiences. To understand the perspectives of special educators regarding promoting summer employment and other community activities for youth with disabilities, the authors interviewed 14 teachers from 10 high schools. Although teachers identified the summer months as a promising avenue for engaging youth in career development experiences, they articulated several school-, family-, and employer-related barriers that may hinder youth from accessing these experiences. This article discusses recommendations for engaging youth more meaningfully during the summer months and offers direction for future research.