Although the Qatari government has invested significantly in education over the past two decades, little research has comprehensively assessed factors associated with high school adjustment and academic success in the country. The present study addressed this gap with a sample of 576 students attending high school in Qatar (M age = 16.32, SD = 1.09; 63.7% male). Students self-reported their school adjustment and perceived academic performance as well as positive and negative indicators of health, including well-being and emotional and behavioral problems. Path models revealed that both well-being and problems contributed to school adjustment. Well-being and problems also contributed to academic performance, but these paths differed for males and females. For females, but not males, well-being was directly related to better performance; for males, but not females, problems contributed directly to worse performance and also operated through school adjustment to affect performance. Implications for promoting optimal school adjustment are discussed.