Cashews are grown by over 3 million smallholders in more than 40 countries worldwide as a principal source of income. As the third largest cashew producer in Africa, Benin has nearly 200,000 smallholder cashew growers contributing 15% of the country's national export earnings. However, a lack of information on where and how cashew trees grow across the country hinders decision-making that could support increased cashew production and poverty alleviation. By leveraging 2.4-m Planet Basemaps and 0.5-m aerial imagery, newly developed deep learning algorithms, and large-scale ground truth datasets, we successfully produced the first national map of cashew in Benin and characterized the expansion of cashew plantations between 2015 and 2021. In particular, we developed a SpatioTemporal Classification with Attention (STCA) model to map the distribution of cashew plantations, which can fully capture texture information from discriminative time steps during a growing season. We further developed a Clustering Augmented Self-supervised Temporal Classification (CASTC) model to distinguish high-density versus low-density cashew plantations by automatic feature extraction and optimized clustering. Results show that the STCA model has an overall accuracy of 80% and the CASTC model achieved an overall accuracy of 77.9%. We found that the cashew area in Benin has doubled from 2015 to 2021 with 60% of new plantation development coming from cropland or fallow land, while encroachment of cashew plantations into protected areas has increased by 70%. Only half of cashew plantations were high-density in 2021, suggesting high potential for intensification. Our study illustrates the power of combining high-resolution remote sensing imagery and state-of-the-art deep learning algorithms to better understand tree crops in the heterogeneous smallholder landscape.