High-impact tutoring has emerged as a primary school district investment for addressing learning loss that occurred during the COVID-19 pandemic. While existing research shows that high-impact tutoring is effective for accelerating student learning, this study examined the school-level facilitators and barriers to scaling high-impact tutoring. Situated in an urban traditional school district and an urban charter management organization, we collected survey and interview data from teachers and administrators to identify scaling challenges. Major barriers to scaling included time and space constraints, tutor supply and quality, updated data systems, and school level costs, while a key facilitator was teacher buy-in. We end the paper with recommendations for how districts can strategically grow their high-impact tutoring efforts.