Actor network theory (ANT) is used to explore how work-learning is enacted in informal online communities and illustrates how researchers might use sociomaterial approaches to uncover complexities, uncertainties, and specificities of work-learning practices. Participants in this study were self-employed workers. The relational and material aspects of work-learning, along with notions of the workspace of the self-employed as hybrid, distributed, and shifting, are considered. This study then examines the work that web-technologies, such as postings, do as they are entangled in an array of networks. Far from being singular objects unified in function, form, or effect, the posting provides multiple entry points for exploring online work-learning practices. The informal learning enacted in this study was the effect of multiple networks and attempts to stabilize fluidity. Different associations with knowledge and novel ways of knowing were also enacted, although there are contradictions between Web2.0 rhetoric and the practices of these self-employed workers. Findings suggest that practitioners and researchers should not be too quick to paint work-learning practices in online communities, or even the notion of online community, with a broad brush.