School leadership research shows that effective practice depends on context. Yet two questions remain open in faith-based schools: how principals vary their leadership across the institutional conditions of schools within a single religious organization, and how far the organization’s values shape that variation. This study addresses both through an interpretive multiple-case study of five Muhammadiyah upper-secondary schools in Karanganyar Regency, Central Java, selected for maximum variation across three institutional conditions: Pioneering, Expansion, and Institutionalization of Excellence. Data came from interviews with principals, vice-principals, and administrative staff, as well as from school documents, and were analyzed through reflexive thematic analysis. A sixth school, first classified as Pioneering, proved to be an established institution and was analyzed as a contrasting case. Principals did not lead through a fixed style. They read each school’s condition and moved among service-oriented, developmental, strategic, and directive modes, and a directive or transactional mode appeared in every condition, not only in struggling schools. The balance tracked institutional condition, from service toward staff with directive control of pupils under scarcity, to a relational base paired with a transactional apparatus during expansion, to service and strategic direction in established schools. Across all conditions, adaptation stopped at limits set by Al-Islam and Kemuhammadiyahan values. The study proposes the Value-Bounded Situational Leadership model, which extends situational leadership from follower readiness to institutional condition and from value-neutral to value-bounded fit