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In this chapter, we theorize about online freelancers’ approaches to work flexibility. Drawing from an ongoing digital ethnography of US-based online freelancers pursuing work on digital platforms, our data question the common conceptualizations around the flexibility of online freelancing. We posit that the flexibility of where to work, not when to work, is the most important attribute of their work arrangement. Our data show (1) the online freelancers in our study prefer the stability and sustainability of full-time work over freelancing when both are offered as remote options; (2) full-time remote employment increases these workers’ freelancing control / flexibility; (3) these workers keep freelance work options open even as they transition to more permanent full-time work arrangements. We discuss how these findings relate to workplace culture shifts and what this means for contemporary working arrangements. Our insights contribute to the discourses on knowledge-based gig work and for what it means to study individuals online.