Any policy should be centered on advancing the cause of well-being, with the ultimate goal being the creation of a just, sustainable, and caring society in which people can prosper and have happy, meaningful lives. The widespread adoption of digital technology has had a profound impact on various aspects of human life, extending beyond its economic implications and influencing people’s wellbeing. The effects of digitalization on wellbeing have sparked a vigorous scholarly debate, yielding divergent findings. In Egypt, promoting digital transformation and enhancing citizens’ wellbeing rank among the government’s highest priorities, evident in its policies and initiatives. Despite significant advancements in Egypt’s information and communication technology (ICT) infrastructure, access, and usage over the past decade, objective and subjective wellbeing in the country have consistently declined. Consequently, this chapter undertakes a critical evaluation of how digitalization affects Egyptians’ subjective and objective wellbeing. Drawing upon a comprehensive examination of Egypt’s ICT industry’s history and evolution alongside wellbeing indicators, this chapter investigates the short- and long-term dynamics between digital transformation and wellbeing. Two separate models are constructed using the autoregressive distributed lag (ARDL) specification. The first model, based on data from 1990 to 2021, reveals a negative short-term relationship between digitalization and objective wellbeing but a positive long-term relationship. Conversely, the second model shows a negative relationship between subjective wellbeing and digitalization from 2005 to 2021 in the long run, and no relationship in the short run. The chapter recommends addressing digital illiteracy and digital divide, and exclusion to bridge the digital usage and coverage gaps, mitigating the potential negative impact of digitalization on Egyptians’ wellbeing. Proposed measures include expanding broadband networks, enhancing digital governance, upskilling and reskilling the workforce, ensuring sound regulation of the IT sector, and building sufficient capacity to transition to advanced mobile broadband generations. By implementing these strategies, Egypt can foster a more inclusive digital landscape that promotes citizens’ overall wellbeing and mitigates the adverse effects of digitalization.