Most of the Iberian Peninsula has a Mediterranean climate, which strongly determines the objectives, strategies and techniques of forest restoration. This communication addresses a main forest restoration challenge for Mediterranean-climate woodlands in Spain: the transformation of old monospecific pine plantations to more diverse, resistant and resilient forest systems. I also present how afforestation methods and some ideas on plant quality have evolved in the last 80 years. Productivity of Mediterranean forests is low, which discourages private owners to invest in woodland management. Therefore, woodland management strongly relies on public funds. Large-scale afforestation in the 20th century has created huge areas of monospecific pine plantations, which have been under thinned and are very simple structurally with almost no understory. The stands are very prone to fires, diseases and drought dieback. However, old pine plantations can facilitate the establishment of late successional trees and shrubs when properly thinned. Therefore, pine plantations are an opportunity for restoring several types of oak-dominated forests at a large scale and resources should invested to preserve and gradually transform these plantations into mixed forests. Funds should be invested in thinning progressively rather than to plant new areas. In many plantations close to oak forests remnants, thinning is the only management required. However, many pine plantations are far from seed sources and enrichment plantations together with thinning are needed. Extensive enrichment plantations are expensive. Therefore, an option is to develop a network of small islets strategically placed inside pine plantations and properly managed as seed foci to foster pine plantation colonization. This option is cheaper than conventional extensive low-density enrichment plantations but research is needed to assess its effectiveness for pine plantation transformation.