In this article, we will discuss different entanglements of technology and masculinity with a special focus on (automated) vehicles. Starting from a cyborg- epistemology formulated as 'thesis, anti-thesis, synthesis, prosthesis' (Gray 2001: 189), we will, in three sections, entangle and disentangle different discourses and practices around how masculinity has been constructed around intimacy, technology, and cyborgisation. Historically, this points in both destructive directions and emancipatory hopes of transcendence through cyborgisation. Cyborgs are thus political technologies, and we argue that a history of masculinity as well as the future of masculinity, in a western context and beyond, can be understood in relation to cyborgisation and intimacy with technological artefacts. It is argued that cyborgs are possibly the tricksters of the future posthuman masculinity but they are also a tool to understand the 'leitmotif' of male transcendence in the history of masculinity. To illustrate our point, we will use different forms of technologies of movement and other man-machine relations as our "objects-to-think-with", considering gendered power relations and emancipatory potentials (Haraway 2004: 321).