Purpose: This paper aims to describe the levels and type of contingency faced by school principals in Chile and the way certain aspects of the Chilean school system result in a greater or lesser presence of these contingencies. Design/methodology/approach: The results reported here are based on the application of a structured questionnaire to 381 elementary school principals in Chile. A “Leadership Contingency Index” was created to analyze the extent and characteristics of this phenomenon, which was complemented with a multiple regression analysis to observe the variables that influence the levels of contingency. Findings: This study has shown that the main contingencies faced by school leaders in Chile revolve around the relationship between actors: assist families, relationship with and among students and resolution of school staff problems. Also shows that the level of contingency faced by principals is strongly conditioned by the socio-educational context of the school and is not related to the individual characteristics of the leaders. This level of contingencies is significantly higher in the public system, although the most recurrent contingencies are the same in each type of school administration (public, private subsidized and privately funded schools). Originality/value: This paper addresses an important but relatively unexplored dimension in specialized research on leadership: variable contingencies under which the leadership role is performed daily, including significant gaps between schools. Understanding and analyzing school leadership from the perspective of the complexity of tasks currently faced by principals, many of them highly unpredictable, ensures a realistic view of the possibilities and limitations of leadership in action and, consequently, provides better tools to strengthen the school leadership role and its contribution to improving student learning.