Digital stress is believed to play a role in the association between social media use and psychosocial outcomes. However, the literature is limited by a lack of measures that conform to published theoretical models of the construct. The present investigation details the development of a new multidimensional measure of digital stress. Based on an earlier conceptualization of Digital Stress (Steele et al., 2020), Study 1 identified items from extant measures of digital stress, conducted a qualitative review of the literature to compose new items, and conducted focus groups with young adults and adolescents (N = 23) to improve item wording and interpretation. Study 2 conducted an exploratory factor analysis (EFA) of items with a young adult sample (N = 247) collected online, yielding support for four hypothesized factors (i.e., availability stress, approval anxiety, fear of missing out [FoMO], and connection overload) plus one unanticipated factor (i.e., online vigilance). In Study 3, college students (N = 174) completed paper-and-pencil surveys, and EFA results showed a similar structure as detected in Study 2. In Study 4, confirmatory factor analysis examining the five-factor model was conducted on data from adolescents (N = 163) and college students (N = 152). These procedures yielded 24 items measuring 5 components of digital stress: availability stress, approval anxiety, FoMO, connection overload, and online vigilance. Associations between digital stress and psychosocial distress and functioning are reported to demonstrate convergent and divergent validity. (PsycInfo Database Record (c) 2021 APA, all rights reserved).