Monitoring the height of secondary forest regrowth is essential for assessing ecosystem recovery, but current methods rely on field surveys, airborne or UAV LiDAR, and 3D reconstruction from high-resolution UAV imagery, which are often costly or limited by logistical constraints. Here, we address the challenge of scaling up canopy height monitoring by evaluating a recent deep learning model, trained on data from the Amazon and Atlantic Forests, developed to extract canopy height from RGB-NIR Planet NICFI imagery. The research questions are as follows: (i) How are canopy height estimates from the model affected by slope and orientation in natural forests, based on a large and well-balanced experimental design? (ii) How effectively does the model capture the growth trajectories of Pinus and Eucalyptus plantations over an eight-year period following planting? We find that the model closely tracks Pinus growth at the parcel scale, with predictions generally within one standard deviation of UAV-derived heights. For Eucalyptus, while growth is detected, the model consistently underestimates height, by more than 10 m in some cases, until late in the cycle when the canopy becomes less dense. In stable natural forests, the model reveals seasonal artifacts driven by topographic variables (slope × aspect × day of year), for which we propose strategies to reduce their influence. These results highlight the model’s potential as a cost-effective and scalable alternative to field-based and LiDAR methods, enabling broad-scale monitoring of forest regrowth and contributing to innovation in remote sensing for forest dynamics assessment.