Changes in species richness along the ecological succession gradient may be strongly determined by coexisting extinction debts of species from the original habitats and colonization credits of those from the replacing habitats. The magnitude of these processes and their causes remain largely unknown. We explored the extinction debt and colonization credit for grassland and forest specialist plants, respectively, and the local and landscape factors associated to the richness of these species groups in a 50-year process of forest encroachment into semi-natural Mediterranean grasslands. A set of sampling plots of persistent grasslands and forests and their transitional habitat (wooded grasslands) was selected within fixed-area sites distributed across the landscape. Our results confirm the extinction debt and suggest colonization credit (according to observed trends and model predictions) in wooded grasslands when compared to persistent forests, despite wooded grasslands and persistent forests having similar tree cover. Grassland connectivity and solar radiation had opposing effects on the richness of both grassland and forest specialists, and it is possible that the availability of seed sources from old forests may have accelerate the payment of colonization credit in the wooded grasslands. These results suggest that extinction debt and colonization credit have driven species turnover during the 50 years of forest encroachment, but at different rates, and that local and landscape factors have opposing effects on these two phenomena. They also highlight the importance of documenting biodiversity time lags following habitat change when they are still in progress in order to timely and adequately manage habitats of high conservation value such as the grasslands studied here.