What happens when we go online, interact and leave our digital footprints? What is the nature of the online spaces that teachers and their students inhabit and the implications of being in these spaces? In this article we have explored these questions by following the theoretical inspirations by James Paul Gee about affinity spaces and Martin Heidegger’s notions on dwelling. The article interweaves its argument with examples from several research projects to argue that online environments allow for opportunities to play and personalize, to be creative, and that these forms of expressions are an interplay of social and technical elements. While the control within digital spaces is not transparent, we contend that there are opportunities for the user to exert influence on and within digital spaces, and to transform them in varying ways and scope. Sometimes those spaces facilitate autonomy and self-selection, which in turn initiates or confirms transformation. With the growth and increased sophistication of virtual realities and artificial intelligence, we need to understand the nature of the educational engagement within these spaces. We also need to understand this mutually influencial engagement between the user and these digital spaces, and be vigilant as to who might be exerting the most influential control.