This paper reflects on media tactics and engagement in amateur media practices from a longue durée perspective. More specifically, it addresses the question how discourses on and from users of different amateur and home movie technologies – from film via home video to digital media – reflect various forms of engagement, adaptation and resistance in amateur user practices. In the history of amateur filmmaking, a wide variety of users can be identified – from family filmmakers to cine-club hobbyists or even avant-garde artists. Differentiating not only between user types, but also between user generations, this paper argues, is helpful for understanding the user dynamics involved in so-called periods of transition, when the introduction of a new media technology brings about an (re)positioning of users vis-à-vis the new media technology’s affordances and constraints within its different contexts of use. Based on a historical discourse analysis of a wide variety of amateur photography, film and video magazines published between 1895 and 2005, the paper aims to provide both a conceptual and long-term historical reflection on this user dynamics involved in transitions of amateur media technologies and user practices. In total four periods of transition will be compared: the introduction of (1) small-gauge technologies in the 1920s and 1930s, (2) Super 8 film technologies in the 1960s, (3) home video technologies in the late 1970s and 1980s, and (4) digital media technologies in the 1990s and 2000s. Distinguishing between so-called ‘first-time users’, ‘adoptive users’ and ‘resistant users’ as together constituting a user generation in these four periods of transition, shows that while tactics and engagement involved in amateur media practices may take different forms throughout time, dependent on user types and contexts of use, actually various continuities (e.g. democratization discourses) and “historical hybridities” can be found in and between user generations of twentieth-century amateur media technologies.