There is widespread concern that species will fail to track climate change if habitat is too scarce or insufficiently connected. Targeted restoration has been advocated to help species adapt, and a “conductance” metric has been proposed, based on simulation studies, to predict effective habitat configurations. However, until now there is very little empirical evidence on how the configuration of habitat is affecting expansion at species' cool range margins. We analysed the colonisation events that have occurred in continuously monitored trap locations for 54 species of southerly distributed moths in Britain between 1985 and 2011. We tested whether the time until colonisation was affected by attributes of each species, and of intervening landcover and climate between the trap and the baseline distribution (1965–1985). For woodland species, the time until colonisation of new locations was predicted by the “conductance” of woodland habitat, and this relationship was general, regardless of species' exact dispersal distances and habitat needs. This shows that contemporary range shifts are being influenced by habitat configuration as well as simple habitat extent. For species associated with farmland or suburban habitats, colonisation was significantly slower through landscapes with a high variance in elevation and/or temperature. Therefore, it is not safe to assume that such relatively tolerant species face no geographical barriers to range expansion. We thus elucidate how species' attributes interact with landscape characteristics to create highly heterogeneous patterns of shifting at cool range margins. Conductance, and other predictors of range shifts, can provide a foundation for developing coherent conservation strategies to manage range shifts for entire communities.