Because digital media simultaneously afford users the ability to support their individual autonomy in ways that benefit them and, for some, erode their control and negatively impact their lives, a growing number of people now seek to disconnect or abstain from using various digital technologies. This study investigates a particular paradox of disconnection that manifests in the discussions of an online community of disconnection — r/NoSurf. Drawing on a mixed-methods analysis of the public discussion records of over 26,000 people who actively contributed to the online community of disconnection, this study highlights peoples’ complex and ambivalent relationships with digital media and the multidimensional and paradoxical ways in which (dis)connection can support digital well-being. The study provides insights into the nature of the discourse within this community, advancing our understanding of what digital well-being is and the ways that people conceive of, and negotiate, various disconnection practices to support their digital well-being.