The coexistence of natural and planted forests is a significant feature in the Mediterranean and other regions of the world. Understanding this dynamic is crucial for assessing forest management. The purpose of this research is to provide a long-term scientific assessment of forest cover dynamics in the Maâmora forest (1989–2022), with the aim of generating new insights into the drivers of cork oak (natural forest) decline and the expansion of plantation forests (Eucalyptus, Pine, Acacia) and bare land. Five Landsat images (1989, 1999, 2009, 2019, 2022) were classified using the Maximum Likelihood Classification (MLC) algorithm, and land cover changes were quantified. Statistical analyzes were conducted using Generalized Linear Mixed Models (GLMs). Over the past three decades, natural forest cover declined by -8.15% per decade, while plantation forests and bare land increased by 4.50% and 312.5% per decade, respectively. This research highlights the conversion of Maâmora's natural forest into plantation forest and bare land, driven by a blend of natural and human-induced factors. Our findings provide valuable insights for guiding rehabilitation efforts and support sustainable forest management. Furthermore, it is essential to adopt specific strategies, including cork oak restoration, assisted natural regeneration, and improved monitoring of forest resources. Future research should explore the effectiveness of these approaches across different ecological and socio-economic contexts to refine forest policy.