The mutualistic breeding system involving fig trees (Moraceae, Ficus) and fig wasps (Hymenoptera, Chalcidoidea, Agaoninae) would appear so specialized that one may wonder at the evolutionary processes that could be responsible for the existence of about 750 species-specific associations. In this paper we present data concerning two cases of species specificity breakdown between African fig trees and fig wasps. We then analyse the possible evolutionary scenarios which could be responsible, as well as the possible evolutionary outcomes of the observed situations. Our analyses range in scale from continental to habitats, and fig crops to individual figs (syconia). Habitat shifts and ecological barriers seem to be the more likely explanations for the evolution of novel fig tree-fig wasp associations, but sympatric and parapatric scenarios cannot be ruled out.