Collaboration is essential in the ongoing project of honing the craft of teaching. The absence of consistent interaction with colleagues and opportunities to learn together, and from one another, reduces teaching to an individual task, carried out in isolation. As technological innovation complicates pedagogical knowledge, educators must rely on one another to advance their practice. Yet, teacher certification exams continue to emphasize finite knowledge of individuals through high-stakes tests that purport to measure teacher quality, an attribute that is, according to David Berliner (2005), nearly impossible to assess. Drawing on the work of our participatory action research group, the New York edTPA Alternative Scoring Consortium, this chapter problematizes the tension between collaboration and isolation in preparing for, and submitting portfolio documents for edTPA. By extension, this analysis illuminates how isolation and collaboration reflect the work of teaching in these digital times.