Novice teachers do not have sufficient opportunities to troubleshoot real-world teaching situations before having their classrooms. Antiquated professional development (PD) models lack the collaboration element that provides authentic application of concepts. This qualitative case study was conducted to fill a gap in research on novice teachers’ voluntary participation in an online community of practice. The study explored how the situated learning in this virtual community addressed the cognitive and social needs of early career teachers as they made the theory to practice connections. The community of practice framework and the social learning theories supported socialization as essential in early career teachers’ growth. Research questions in the study examined five teachers’ beliefs about collaboration in promoting community engagement, the influence of voluntary participation on the quality of teacher engagement, and teachers’ perceptions of the use of Web 2.0 technology to build community. A priori codes were created using the theoretical frame and research questions to guide the analysis of audio, transcriptions, observations, and other coded artifacts to find themes and patterns promoting internal validity. Findings revealed teachers’ belief in collaboration impacted their level of engagement virtually. While voluntary participation motivates teacher participation, it does not guarantee high-quality engagement without accountability. Since attrition is a continual threat to the teaching workforce, study results validate recommending the use of virtual resources to facilitate CoPs to remedy the mentoring and coaching void for early career teachers. Also, innovative use of Web 2.0 tools should be used to expose new teachers to diverse experiences that bridge theory to practice gaps and encourage teacher leadership, which promotes retention.