Workplace digitalization created a sea change in work practices and it altered the situation of older workers. Digitalization entails the increased use of digital technologies, such as computers and online services. Older workers often possess limited digital skills, which may put their labor market participation at risk. Previous studies began exploring how older workers fare when their workplaces are digitalizing. However, the research field is still emerging and remains fragmented. This article comprises a systematic literature review that takes inventory of what we currently know about older workers in digitalizing workplaces. It demonstrates that older workers experience the digitalization of their workplaces in various areas, reaching from health monitoring to work arrangements. Interestingly, challenges and opportunities emerge in each area affected. This Janus-faced situation underlines the complexity of consequences, and it raises questions about social inequalities in these consequences. The work environment plays a crucial role in shaping how older workers experience workplace digitalization. It shapes which options for adaptation they have, and to which degree they can act on these options. This circumstance makes workplaces an excellent starting point for interventions. Country-characteristics likewise exert an influence. While characteristics such as retirement regulations are purposefully modified for intervention, other characteristics, such as culture, are not. This circumstance limits governmental options for shaping the situation of older workers in digitalizing workplaces. Future research should further explore the situation of older workers in digitalizing workplaces, paying special attention to the theoretical framework and to developments in the wake of the COVID-19 pandemic.