This article presents the results from an empirical qualitative study of the challenges faced by teacher leaders in their attempts to work directly with their colleagues to change instructional strategies and improve student success. Additionally, it offers a challenge to the utility of a naïvely espoused theory of distributed leadership, which becomes the theory in use, to improve leadership capacity with the goal of improving classroom instruction and student success. Six teacher leaders at an urban elementary school were studied for 1 year. The challenges faced by the teacher leaders were categorized under three themes: dealing with conflict, negotiating competing agendas/responsibilities and balancing microdiversions, and frustration with lack of influence and impact. It was concluded that the challenges experienced by teacher leaders, those whom leadership is distributed among, are problematic and underestimated. Moreover, we assert that distributed leadership as a theory in use falls short when the espoused theory is naïvely conceived. We do, however, offer recommendations for overcoming the challenges experienced by these teacher leaders, which we hope might help reconcile the disconnect between a naïvely espoused theory of distributed leadership and the resultant theory in use.