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