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This qualitative study seeks to understand how nine first-year urban mentors conceptualize mentoring across the school year, and their professional needs and challenges. The data indicate that with the transition from experienced urban teacher to novice mentor comes a range of challenges. Mentors must learn to navigate multiple new and complex relationships with administrators, teachers, students, and other mentors while simultaneously attempting to establish credibility and skill in enacting mentoring practices. Mentors valued initial and ongoing professional development, though they struggled with the application of tools in situ and with individualizing the mentoring process to meet each new teacher’s diverse needs. Recommendations include providing sanctioned time to collaborate with and shadow experienced mentors, and scaffolded practice with tools and processes.