The aim of the present paper is to discuss the problems with attempts to increase forest area in Poland (with a focusing on afforestation in the last 30 years), to analyse the discrepancy between the afforested area and the recorded increase in forest area, and to identify solutions that could enable Poland to achieve the policy goal of 33% forest cover by 2050. The study is based on available official documents, statistical data, and the existing literature. It presents the results of a postal survey of key institutional actors involved in afforestation in Poland on the factors hindering the implementation of afforestation on private land. The study shows that the main factors influencing the collapse of afforestation are long-term, and it is unlikely that this trend will be reversed in the coming years. However, it appears possible to take steps to convert forested agricultural lands that meet national criteria for recognition as forest to forest. The urgent need to protect biodiversity and improve environmental quality in the face of climate change makes it necessary to develop and implement a new program to increase forest area and to provide coherent tools to support the conversion of forested agricultural land to forest.