The purpose of this research is to examine configurations of proactive personality and ICT-enabled technostress creators as drivers of job crafting for Gen Z, Gen Y, and Gen X+ workers. Adhering to configurational theorizing, the study was conducted using fuzzy set qualitative comparative analysis (fsQCA). Survey responses collected from 335 full-time workers revealed that the presence of a proactive personality was a necessary condition for job crafting to occur within the context of ICT demands for these generations. Four configurations for Gen Z, five configurations for Gen Y, and four configurations for Gen X+ workers revealed sufficient conditions for job crafting. The present research contemporizes Job Demands-Resources (JD-R) theory by incorporating ICT as a modern-day job demand. In using fsQCA as a novel qualitative methodological tool, this research offers new meaning to the prior regression-based findings regarding proactive personality trait's relationship with job crafting.