This chapter explores how research and practice that draws on spatial and transdisciplinary methods and approaches can be enhanced or hampered by social learning. To this end, I first provide a working definition of social learning; the distinction between multi-, inter- and transdisciplinarity; and the take on spatial and transdisciplinary research and practice. Afterwards, studies on social learning relative to planning, transdisciplinary research, transdisciplinary co-production and action-oriented knowledge are reviewed. Since these studies urge for sustainability to be understood and pursued anew, both potentialities and challenges to render novel attempts at sustainability transformative are underscored. Finally, I retrospectively deconstruct my practical experience in the production of local master plans in Costa Rica, my homeland, in view of the foregoing sections. In doing so, transdisciplinarity and spatial methods are taken to be characterised and deployed according to varied—and even disparate—logics within research and practice. All in all, I conclude that more pragmatic ways to further urban sustainability need not only champion social learning but also, besides transformative, practical-normative implementations, should be iterative, incremental and aimed at systemic change.