The present study examines from the contingency opportunities perspective the influence of contextual factors on principals' learning-centered leadership using HLM. Participants were 18,641 school principals from 73 jurisdictions who participated in the Programme for International Student Assessment (PISA) 2009. Results showed that principals were able to differentiate strategic (academic focus) from operational (involvement) leadership. The second finding pertained to principals shifting their leadership priorities when confronted with student academic failure and when leading larger schools. The third finding was the increase in both aspects of principals' leadership in the face of parental academic pressure. The fourth finding was the negative impact of shortage of information technology resources on involvement. The last finding was that the Organisation for Economic Co-operation and Development (OECD) variable moderated the influence of parental academic pressure on academic focus, and that principals in OECD jurisdictions reported more involvement than those in non-OECD jurisdictions. The present study affirms principals' behaviors as agentic responses to environmental contingencies.