This thesis explores the effect of technological innovation on the construction of the cinematic essay, with a particular emphasis on the ways in which digital tools have shaped the form in the early twenty-first century. I first argue that the cinematic essay has been associated with technological evolution throughout its history, and then discuss recent examples of the form which utilize aesthetic strategies, editing techniques, and modes of spectatorial address that are rooted in the capabilities of digital technologies. Drawing on theories of the essay as a literary mode by Michel De Montaigne, Theodor Adorno and György Lukács, and connecting them to a range of theoretical work on intellectual montage and reflexivity in cinema, I outline an understanding of the cinematic essay as an innovative, self-reflexive form of filmmaking which foregrounds the act of its own making. My aim is to highlight that essay filmmakers have consistently implemented new filmmaking technologies into their craft to explore their potential for opening new opportunities for essayistic expression, while simultaneously reflecting on the ways in which the development and proliferation of these new technologies have transformed the wider landscape of cinema. I take as my primary case studies three essay filmmakers who have embraced technological innovation throughout their careers, and produced a variety of work using film, video and digital: Harun Farocki, Chris Marker and Jean-Luc Godard. Focusing on their late works, I illustrate how each filmmaker’s interaction with digital technology influenced their approach to crafting essayistic discourse and how their experimentation with digital image-making tools critically tackles wider intellectual concerns related to the digitisation of visual culture in the early 21st century. Subjects dealt with throughout this thesis include interactivity, simulated imagery, the democratisation of filmmaking resources, dialogical exchange, intertextuality, and digital archiving methods.