Vice-principals' (VPs) work is intensifying in its complexity and volume but the changing nature of their work is not thoroughly documented. This article focuses on the often-overlooked VP's role and records the factors that evidence the intensifying work conditions for VPs. The data for this article come from a large-scale online survey that has been distributed among the VP members of the Ontario Principals' Council (OPC). The research findings comprehensively document the increasingly complex and multifaceted nature of VPs' work and highlight the specific challenges facing VPs, particularly in the areas of motivation and expectation gap, duties and responsibilities, policy influence, challenges and possibilities, emotional well-being and coping, and mentoring. This study provides evidence of the need to reexamine the role of VPs and an urgency to provide targeted training, mentorship and professional development to VPs so that they can flourish in their roles.