Job demands overburden school administrators' personal and professional capacity and affect their performance and well-being. However, studies on principals and vice-principals' work intensification fail to highlight how their work demands and challenges are manifested, and how work demands contribute to the changing nature of their work. This qualitative study explores in what ways job demands are manifested in school administers' intensified work conditions and how their perceptions of job demands help them create a sense of control. The study utilizes the job demands model as a framework to help closely examine two types of job demands: job challenges; and job hindrances though principals' accounts. The results show that job challenges tend to be transitory and are more likely to be overcome; job hindrances however tend to be more institutional and less temporary and harder to overcome. Attempting to deal with job challenges the same as dealing with job hindrances may become challenging itself and build up rather than alleviate work-related stress among school principals.