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The principal supervisor role has been redesigned in many large urban districts, but we know little about how principal supervisors in mid-size districts contribute to principals’ instructional leadership growth. This qualitative case study addresses this gap by examining how district shepherds (aka principal supervisors) enact their roles and by exploring the key work tasks in which they engage with principals at underperforming schools in 5 mid-sized districts enrolled in one university partnership program. We found that district shepherds who provided support to principals, and did not supervise, mostly engaged in talk moves and classroom observations with principals. District shepherds who also served as the principals’ supervisors (i.e. evaluators) engaged in joint work tasks related to principals’ roles as instructional leaders.