Preserving forest legacy was an important objective throughout Romanian history and so is today. Artificial forest regeneration (including both reforestation and afforestation) was widely used to ensure the forest continuity, following forest harvesting, or to create new forests on non-forest lands. As Romania has undergone various political changes that affected the socio-economic environment, these changes also left significant marks on forest cover dynamics. In this paper, we chronologically present the historical initiatives to preserve and increase forest cover in Romania, the current practices, available funding and future perspectives on artificial forest regeneration. Increasing forest cover from the current level of 27% to, and beyond European average of 33% seems an ambitious target for Romania. However, that may be achievable if the sources of funding for afforestation would diversify and increase, the available funds would be more effectively accessed, national forestry regulations would be less bureaucratic and the guidelines on artificial forest regeneration would be up to date and less restrictive. The whole framework of forestation should be revised to comply with recent social, economic and environmental realities, and modern criteria and indicators for sustainable forest management should be explicitly included. The new goals should also be tailored to the changes regarding the property type, climate related trends and new requirements of the forest certification systems.