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Research exploring the intensification of school principals’ work on their well-being has largely been conducted in developed countries. Given the geopolitical influence of North American education system on the Caribbean and Jamaican contexts, the researcher used a qualitative study to explore the well-being issues secondary school principals deal with in Jamaica. Twelve principals working in schools supporting rural, urban, and inner-city communities in Jamaica were interviewed using conversational semi-structured interviews. Results indicate that principals experience work-related stress and overwhelmingness, anxiety, fatigue and low energy, and exhaustion and frustration when carrying out their leadership and management work-related duties. This paper, therefore, aims to highlight how different well-being issues influence Jamaican secondary school principals paid and unpaid work-related duties.