This paper looks at the complex impact of urban migration on smallholder agriculture in Ilima, Kenya. Specifically, it examines topics around food security, soil erosion, the use of remittances, agroecological practices, and the values that underpin these. Ilima, a small, rural village in Makueni County, Kenya that is experiencing large amounts of urban migration was used as a case study. A total of 33 households were interviewed, 29 in Ilima and four in urban centers. It was found that many residents, including youth, want to invest in agriculture in Ilima, but multiple barriers exist, causing migration and the land to become fragmented and degraded. The main barrier was found to be small land size. Remittances showed a positive association with food security, but the pathways remain unclear.