Pathways to Success in the Kittery School District addressed the social and emotional needs of military-connected students and engaged both students and parents in college and career readiness activities. Key program strategies included peer support programs, professional development for school staff, parent engagement programs, college visits, and a grant project coordinator who served as a community engagement specialist. The intent of the Pathway to Success initiative was to mitigate the transitional challenges for military dependent students in Kittery Public Schools, and build the school system’s awareness of the unique needs of military dependent students to better prepare them with the skills needed to develop and achieve their postsecondary goals. SEG tracked the project's fidelity of implementation; SEG also provided process and summative evaluation reports annually and provided the school district with semester status reports. Data collection methods included an annual district climate survey, annual site visits, and teacher surveys. The project was supported by the Department of Defense Education Activity (DoDEA).