Digital media technologies play a fundamental role in Kuwait’s plan to transition away from its dependence on hydrocarbon exports and toward a knowledge-based economy. The nation has already made significant progress in the realm of digital connectivity, ranking among the world’s most connected countries on several important measures; the advantages of which were demonstrated by the important role of Information and Communication Technologies (ICT) in sustaining social, economic, and educational activities during the COVID-19 pandemic. However, less is known about the human elements of digital transformation in the country and the degree to which systematic “offline” disparities among local and expatriate residents continue to perpetuate socio-digital inequalities “online.” Using the Corresponding Fields Model as the starting point from which to theorize the domain-specific links between social and digital inequalities that can amplify or counter historical inequalities, this paper presents key findings from a national survey of 746 residents conducted between October 2020 and January 2021 across four domains of ICT usage (economic, cultural, social, and personal). Although access to the internet through digital media technologies is nearly universal, stark variations in how people go online exist according to age, gender, and nationality, with for example, smartphones serving as the only internet-accessible device for approximately one-third of Asian expatriates. Unlike many countries in the Middle East and North Africa, women in Kuwait do not demonstrate a significant gender gap in the areas of ICT access, uses, or outcomes, showing higher levels of personal internet use, owning more devices, and producing better work-related results with ICTs than men. Nevertheless, women do frequently score lower than men in the domain of skills, where age is also a highly significant factor. Educational differences also relate directly to the persistence of a digital divide within Kuwait, where less than 25% of residents are educated beyond the high school level. The least educated own the fewest number of devices, possess lower skills across every area, engage in the least amount of ICT usage for most personal and economic activities, and derive the least satisfaction from most outcomes pertaining that ICT use. Interventions to address digital inequalities are suggested, as efforts to ensure more equitable access, skills development, and the achievement of tangible outcomes that benefit diverse communities in Kuwait can further bolster the positive dividends of society’s digital transformation as a whole.