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Principals’ work requires a high level of cognitive attention and capacities to effectively exercise judgements, make decisions, solve problems, and learn and process new information in their daily operations of schools. This state of cognitive ability is essential for principals to maintain work productivity and effectiveness. Work intensification in recent years have complicated principals’ work and made it cognitively demanding, leading to cognitive overload and fatigue, and significantly impacting their cognitive wellbeing (CWB). This exploratory study utilizes structural equation modeling to examine principals’ CWB, its manifestation and identifies professional, organizational, and structural factors that are impacting principals’ CWB.