The generation of reliable and up-to-date national land cover information is essential for environmental management, climate action, and territorial planning. In Colombia, the CORINE Land Cover Colombia (CLCC) framework has been the official reference for land cover monitoring since 2000, traditionally updated through expert-based Computer-Assisted PhotoInterpretation (CAPI) at a 1:100,000 scale. However, increasing demands for higher spatial resolution and more frequent temporal updates have made process optimization necessary, driving the incorporation of cloud-based processing and artificial intelligence (AI), including machine learning and deep learning algorithms. This study presents a semi-automated methodology for generating a new generation of harmonized CLCC-compatible raster land cover maps at a 1:50,000 scale—offering four times greater spatial detail than the official vector product—with the capacity for semi-automated annual updates. The approach combines legend harmonization from 55 to 23 classes, historical CORINE Land Cover (CLC) polygon-guided sample generation, spectral stability analysis, and regionalized classification across 190 homogeneous subregions, supported by a reproducible cloud-based architecture. National land cover maps were produced for 2020, 2022, and 2024 with thematic accuracies above 80% and Kappa coefficients up to 0.87, alongside change maps for the 2022–2024 period capturing key dynamics in agricultural frontier expansion, wetland variability, and urban expansion. The resulting products also provide structured inputs for expert-based CAPI workflows, supporting the continuous updating of the official 1:100,000 CLCC map. The results demonstrate the operational capacity of integrating AI, cloud computing, and expert knowledge to strengthen Colombia’s national land cover monitoring system.