This study examined the differences in relationships among system quality, user satisfaction, and enterprise-wide diffusion in cloud-based digital transformation, according to workplace (headquarters vs. field) and generation (MZ Generation vs. older generation). In this study, a mixed-method research design was adopted, integrating quantitative methods through Partial Least Squares Structural Equation Modeling and qualitative methods through interpretative analysis assisted by generative artificial intelligence techniques. The analysis indicated that, for headquarters employees, the findings were consistent with established theoretical perspectives, demonstrating the sequential relationship of system quality leading to user satisfaction, which in turn facilitated enterprise-wide diffusion. In contrast, for field workers, system quality directly impacted diffusion intentions without the mediating role of user satisfaction. The analysis revealed that system quality significantly influenced user satisfaction among both headquarters employees and MZ generation. However, no notable generational differences emerged regarding the impact of system quality and user satisfaction on enterprise-wide diffusion. These findings suggest that although generational differences are present in the formation of satisfaction, the mechanism linking satisfaction to diffusion intentions functions consistently across generations once satisfaction has been established.