The article reports an empirical research study documenting how an integrated playwriting program within an urban, low-socioeconomic status middle school with a majority Latino/a population facilitates increased students' confidence regarding writing in addition to helping students learn transferable writing skills as measured by a districtwide writing sample. Students in the playwriting program with variable levels of writing skills are quantitatively compared with similar students in traditional language arts classrooms of the same urban school. In addition, qualitative methods are used to explore quantitative findings. To delve into possible reasons for these findings that are based on quantitative and qualitative research methods, the discussion of the results is informed by sociocultural learning theory with an emphasis on communities of practice and the motivational theory of self-determination.