This research examined factors that influenced teachers’ decisions to participate in professional development activities and, subsequently, to implement ideas gained through their participation. Twenty-four teachers, employed by an urban school district, shared their perceptions regarding the content, context, and process of a district-wide professional development initiative, focused on digital age literacy skills. Results emphasize how factors that are both internal and external to the teacher influence teachers’ decisions to adopt and implement initiative-promoted strategies. Teachers’ perceptions of the sustainability of new classroom practices, gained through the initiative, are also discussed.