The study is aimed at understanding why some IT employees in India cope better with Work-From-Home (WFH) arrangements by examining how job-related factors and personal characteristics combinedly predict employee well-being. Using primary data purposefully collected from 391 IT professionals engaged in remote or hybrid work in India. The study uses hierarchical multiple regression to assess the gradual contribution of demographic, job-related and personal factors to well-being. It is observed that demographic and home-context variables explain 22.6% of the variance in well-being, with marital status, family size, dependent care responsibilities, workspace availability and reliable internet are observed to have a significant influence. The inclusion of job-related factors increases explained variance to 53.8%, demonstrating that work system design is significantly predicting well-being. Workload escalation exhibits a strongest negative impact, followed by boundary permeability, digital monitoring intensity, role ambiguity, meeting load and career insecurity, all exerting statistically significant adverse effects. The final model explains 64.7% of the variance after adding personal variables. Coping style emerges as the strongest positive predictor of well-being, indicating that adaptive stress management substantially improves outcomes, whereas workaholism independently and significantly reduces well-being. The persistence of strong job-related effects even after accounting for personal and demographic factors suggests that individual resilience cannot compensate for structurally poor remote-work atmosphere.