Woody encroachment (WE) and agricultural expansion are widespread in tropical savannas, where they threaten biodiversity and ecosystem function. In Africa's largest savanna, the miombo woodlands, cropland expansion is expected to cause extensive habitat loss over the next 30 years. Meanwhile, widespread WE is altering the remaining untransformed vegetation. Quantifying the extent of both processes in the Angolan miombo woodlands (~570,000 km2) has been challenging due to limited infrastructure, a history of conflict, and widespread landmines. Here, we analyze spectral satellite imagery to investigate the extent of WE and cropland expansion in the Angolan miombo woodlands since 1990. We asses WE using two complementary metrics: multi-decade canopy greenness trends and conversion from grassland to woodland. We also examine whether WE trends are driven by landscape fragmentation and decreasing fire frequency. We found that from 1990 to 2020, 34.1% of the Angolan miombo woodlands experienced significant WE or was converted to cropland, while open grassy vegetation declined by 62%. WE advanced rapidly even in areas experiencing extraordinarily high burn frequencies and was not adequately explained by changing temperature or precipitation. WE was concentrated far from the agricultural frontier, in remote areas with low population densities. These results challenge the hypothesis that human-altered fire regimes are the primary driver of WE in mesic savannas. The results will help decision-makers conserve the miombo woodlands' biodiversity and ecosystem services, by highlighting that strategies to slow habitat loss must address WE and cropland expansion together