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Contingent workers like freelancers, temp agency workers, contractors, on-demand gig economy workers, and domestic workers now comprise over fifteen percent of the US workforce. Part of the growing chasm between ‘good’ jobs and ‘bad’ jobs, this kind of work is not only unstable, but it also leaves workers without the benefit structure that a company typically provides. One proposed solution to this is ‘portable benefits’ – i.e. those that are tied to the worker instead of the company, thereby allowing a benefit structure to follow workers wherever their work brings them. A nascent policy movement is coalescing around the idea, with proposals to fund experiments in portable benefits structures and studies commissioned to explore them. Yet, despite the heterogeneity of contingent work, it seems that one type of worker – those whose work is arranged through an online app – has heretofore dominated the policy conversation. Through a textual analysis of policy documents, including committee hearing recordings, council meeting notes, text of the proposed bills, and administrative rules, I examine the ways in which policy has to account for technology when it comes to portable benefits, and, conversely, how it is technology that is in many ways driving the need for policy. I then take up the empirical case of one such portable benefit experiment: Alia, the National Domestic Worker Alliance’s new app designed to furnish portable benefits for housecleaners. With ethnographic fieldwork during their year of launch, I document and analyze both the technological and political implications of their design.