This study reviews generational differences in adopting Human Resource (HR) self-service portals (SSPs) within the Nepalese banking organizations. It integrates Generational Cohort Theory with technology acceptance models to analyze adoption drivers, barriers, and organizational support needs. It has three key findings: Generation X prioritizes pragmatic usefulness, Millennials emphasize ease of use and social influence, and Generation Z demands seamless, mobile-first, and consumer-grade experiences. The study shows that barriers are multidirectional, with older cohorts struggling with unfamiliarity and younger cohorts expressing dissatisfaction when systems fail to meet elevated expectations, a phenomenon called “reverse anxiety.” ‘Organizational support’ as a critical moderator, requiring differentiated approaches such as structured training for Gen X and flexible, self-directed resources for younger cohorts in the application of SSPs in organizations has been identified. The study shows that Nepalese banks need to design multi-generational digital HR strategies balancing inclusivity, usability, and efficiency.