Purpose: Concepts of values-based leadership posit that school principals' professional practice must be informed by values to ensure coherently purposeful activities. Contingency models stress the contextual dependency of professional practice and the need to match activities to local opportunities and constraints. The purpose of this paper is to reconcile both positions from an integrative perspective and to illustrate examples of "values-based contingency leadership" (Day et al., 2001). Design/methodology/approach: Analyses draw on survey data from 56 German schools in order to relate professional values stated by the principals as well as organizational features of their schools to teacher ratings on leadership behaviour (n = 910). Instead of scrutinizing singular variables in isolation, a typological approach serves to identify value profiles as well as organizational configurations. Analyses of variance are applied to examine the combined effects of both factors on leadership behaviour. Findings: Interactional effects in the sample indicate that contextual influences are not homogenous across differing value profiles of principals who operate under equal conditions. Descriptive patterns of leadership behaviour within each organizational configuration reveal how principals accentuate leadership activities according to their value profile. Research limitations/implications: Due to the low statistical power of the small sample, findings are clearly exploratory in nature. However, replication and extension studies seem fruitful, as effect sizes of value-context interactions are consistent with theoretical assumptions and not artificially inflated by common-source variance. Originality/value: This paper elaborates and exemplifies the moderating role of values in contextual influences on leadership behaviour. It also provides deeper insights into the content and structure of professional values advocated by school principals.