This chapter examines ‘health’ fitness and lifestyle management in relation to neoliberal moral self-disciplinary discourses, which position the human being and body as a subject to be worked upon. This neoliberal ideology stemmed from a distancing from state interventions, through the promotion of the idea that individuals have a responsibility towards wider institutional, systemic and capitalist systems of control, which situate the ‘indebted man’ as the subjective figure of contemporary capitalism (Lazzarato, 2006). The ‘indebted’ population, therefore, is a paradoxical structure of neoliberal societies, whereby debt must be fulfilled in order to be ‘free’. As Rose (2007: 90) asserts: ‘subjects obliged to be free were required to conduct themselves responsibly to account for their own lives.’ The moral dimensions within dominant ‘health’ discourses have become inherent within current self-surveillance practices (as discussed in Chapter 3) and the regulatory design of self-tracking apps, devices and the sharing of related content on social media. Within discourses of self-tracking and ‘bad’ health, self-worth can become tied to data (Carmichael, 2010). This chapter critiques these discourses, to examine the problematic and moral issues that arise from adhering to such regulatory practices. This book draws upon the definition of moralisation as proposed by Paul Rozin (2011: 380), as ‘the acquisition of moral qualities by objects and activities that were previously morally neutral’. These ‘health’ surveillance and tracking practices intrinsically assign an individual moral obligation to preserve one's own health as public duty, free from state or institutional support (Knowles, 1997: 64). This discourse of ‘shame’ and guilt was identifiable throughout this research project's empirical data, embodied in relation to ‘bad’ and ‘unhealthy’ decisions. This chapter examines the (perceived) lack of self-discipline, health anxieties that legitimate inactivity, self-surveillance and the moralism of body image and, lastly, the burden of self-surveillance and self-tracking as some of the key moralising and regulatory practices of the digital health self today.