In this chapter, I analyse how humans navigate recurring processes of digital disconnection and articulation work to manually repair and reconnect with their wearable devices. I ask what these processes tell us about the relations we form and experience as meaningful with our devices. Specifically, interviews and photo diaries on body-technology relations were conducted with couriers doing delivery services on app-based platforms, with employees who have volunteered themselves to have a microchip implanted in their hand, as well as with self-trackers using tracking devices embedded with sensors for various purposes in their private life. The vignettes in the analysis show how participants constantly navigate moments of disconnection and connection with their devices, resulting in them having to fix the breakdowns to stay connected and work on maintaining a meaningful relationship with their personal tracking device. The analysis shows how the characteristics of this work depend on the context of tracking, the material aspects and physical proximities of the relation between body and device, and the generated data.