Historical biological interactions among peripheral landmasses on the periphery of the Indian Ocean Basin (IOB) are generally poorly understood. While interactions based on early Gondwanan vicariance have been used to explain present day lineage distributions, several recent studies have instead inferred dispersal across the IOB. This inference is often advanced because lineages under study have species inhabiting IOB islands. Here we examine the roles of continental vicariance vs. trans-IOB dispersal in the distribution of an avian genus found around the perimeter of the IOB. A molecular phylogeny does reveal evidence of a relationship that would require the inference of trans-IOB dispersal between eastern Africa and Sri Lanka. However, molecular clock data, ancestral area analyses and paleoclimatic reconstructions suggest that vicariance related to tropical forest expansion and retraction is more likely to have facilitated African–Asian interchange, with an initial colonization of Africa from Asia quickly followed by a recolonization of Asia. Subsequent dispersal from Asia to Sri Lanka and islands east of the Sunda Shelf are inferred; these latter islands were colonized in a stepping-stone fashion that culminated in colonization of the Sunda Shelf, and a recolonization of mainland Asia. We propose that circum-IOB distributions, which post-date early Gondwanan breakup, are most likely the result of continent-based vicariant events, particularly those events related to large-scale habitat alterations, and not trans-IOB dispersals.