Digital-era newsworkers in the United States have steadily joined trade unions since 2015. This article examines all 22 collective bargaining agreements (CBAs) of one such union, the Writers Guild of America, East (WGAE), which were ratified between April 2015 and June 2022, with an eye toward better understanding employee digital job and life satisfaction. Bringing together critical political economy of media, industrial relations, and labor research, the article argues that the collective bargaining agreement is a communicative means through which digital newsworker unions express employee resistance to particular labor issues. It is also a legal mechanism articulating solutions to these issues that could provide the basis for employee life satisfaction. Grounded in a content analysis, this article finds that the WGAE CBAs incorporate language on workplace rights, newsworkers’ benefits, and limits on management rights, revealing the relative weight of different union solutions to newsworkers’ digital-era grievances. The CBAs also communicatively constitute the conditions for digital newsworkers’ happiness and subjective well-being. By proposing a relational model of digital newsworkers’ CBAs, researchers and practitioners could better understand the language that is needed to communicatively constitute and facilitate happiness in newsrooms, supporting digital job and life satisfaction among newsworkers.