Former coalmining communities are often portrayed as regressive and/or resistant to change due to deep dependence on carbon-intensive systems. Emerging research highlights the (latent) potential of post-coal affordances as endogenous social or material features that can create new political possibilities for such communities. However, affordances do not always translate into action, and post-coal transitions within and across Europe exhibit mixed experiences. Therefore, we examine how communities negotiate and navigate new possibilities through processes of wayfinding, spanning institutional, cultural, and everyday practices. We comparatively examine the towns of Loos-en-Gohelle (France) and Whitehaven (England), which, despite their shared coalmining pasts, are evolving in very different directions. Based on 49 semi-structured interviews and detailed field observations, we find that these practices refract within complex and fractious political settings, where industrial capture, governmental neglect, and persistent socio-economic inequalities can confine possibilities for action. We thereby demonstrate that the capacity for change is a product of ongoing political work both within and outside these communities. This enriches existing work on post-coal affordances by drawing attention to the social and political dynamics involved in their mobilization, thereby highlighting their contingency.