Initiatives to integrate technology into teaching and learning often lack a long-term follow up to gauge if those same initiatives set the stage for teachers to easily adopt the next stage of learning technologies. Using the ten-year anniversary of the Commonwealth of Pennsylvania's Classroom for the Future grant, where $200 million were allocated for a statewide technology initiative to promote 21st century teaching and learning, this study's aim was to understand what type of barriers in-service teachers perceive regarding the use of social media communication technologies as a legitimate pedagogical tool. Participants were selected using a multi-stage cluster sampling method to ensure rural, town, suburban, and urban teachers were represented. Using the action areas suggested by Ashton et al. (1999) and Bonk et al. (2001), pedagogical, social, managerial, and technical; a typological analysis was done using the responses of 140 Pennsylvania secondary teachers' stated discouragements. During the analysis a fifth typology, internal school systems, emerged from the data. The most prominent categories were technological and managerial followed by social, internal school systems, and pedagogical. Ultimately, teachers feel that social media communication technologies are not viewed as legitimate teaching tools. To help teachers feel social media communication technologies are legitimate teaching tools policymakers and school leaders are encouraged to create an atmosphere that promotes administrative support, schedules that incorporate planning, and funds to provide ongoing training for teachers to stay current with technologies.