This article presents the findings of a collaborative autoethnography (CAE) of three teacher educators' work as literacy professional development (PD) leaders in a high-needs, culturally diverse, urban, US school district. The research questions focused on what the facilitators learned about leading literacy PD in a high-needs/high-stakes environment and how the teacher educators changed from navigating the complex contexts of PD work over an 18-month period. Data collection included written accounts of the researchers' experiences, collaborative dialogue and probing discussions, and expanded autoethnographic writings. Methods of CAE analysis were employed, resulting in several thematic assertions that offer intimate insight into the processes of facilitating literacy PD with marginalized populations of students and educators. The findings address the socio-political nature of building relationships in such settings, the challenges of changing a deficit-based discourse, and the tensions that influenced the PD facilitators' actions and learning. Through the self-study methodology of CAE, this work provides teacher leaders and teacher educators with tangible ideas about how to facilitate the vital PD processes of relationship building, collaborating with teachers, navigating multiple roles, designing learning engagements and leadership structures, and supporting resistant and struggling educators.