This chapter explores how media representations shape public and organisational perceptions of older workers’ digital engagement. Often portrayed as digitally resistant or dependent, older workers, defined as individuals aged 55 years and above, are often subjected to ageist assumptions that influence hiring, training, and professional development. Through a literature review, the chapter examines how these portrayals reinforce digital inequality across first-, second-, and third-level digital divides. It specifically considers how media narratives intersect with workplace norms and contribute to broader ageism. The discussion is structured around key themes: dominant portrayals in the media of older workers in the workplace, broader depictions of digital engagement, paradoxes in digital literacy acquisition, and evolving narratives during the COVID-19 pandemic. While some representations challenge stereotypes, many continue to obscure the complexity and diversity of older workers’ digital experiences. The chapter highlights the dual role of media in both perpetuating and potentially transforming perceptions of older workers within an increasingly digitalised society.