<p>This study investigates how entrepreneurial passion, career adaptability, and environmental support influence entrepreneurial success in Tunisia's post-revolutionary transitional economy, with attention to gender and regional variations. Using a quantitative survey of 387 Tunisian entrepreneurs and PLS-SEM analysis, all three factors significantly predicted entrepreneurial success, collectively explaining 52.3% of the variance. Entrepreneurial passion (<i>β</i> = 0.328) emerged as the strongest predictor, followed by career adaptability (<i>β</i> = 0.297) and environmental support (<i>β</i> = 0.284). Gender moderation revealed that environmental support has a stronger effect on female entrepreneurs (<i>β</i> = 0.341) than males (<i>β</i> = 0.252), while regional analysis showed that entrepreneurial passion is more critical in resource-constrained areas and environmental support matters more in developed regions. The findings suggest that entrepreneurship support programs should be gender-sensitive and regionally tailored, with career adaptability training integrated into entrepreneurship education. This study contributes novel insights into entrepreneurial success factors in North African transitional economies and advances contextual entrepreneurship theory through the identification of gender and regional moderation effects.</p>