The country of Georgia has an ancient culture with a deep agricultural history. In recent years, small to medium-sized agricultural producers have struggled to grow while the country's policy agenda has turned towards economic modernization. Incentives for foreign investment in the service sector and urban development left a void of policy support for the agricultural industry that has consequently created significant regional imbalances as well as domestic hurdles for producers. In this study, 342 Georgian smallholder farmers were surveyed, 22 participants in focus groups were interviewed and 2 experts were consulted on the findings of the challenges associated with the upscale of small-to-medium-sized farms. The results of the surveys and focus groups show that the key challenges for upscaling small-to-medium-sized farms are (a) policy regulation related to the imported agricultural goods, and challenges with safety regulation for agricultural input products, these policies are essential for the protection of domestic agricultural producers, (b) disconnection between policymakers and farmers (c) lack of vocational education opportunities for farmers to improve their agribusiness and (d) shortage of qualified professionals in agricultural fields to support farmers through private consulting organizations as well as agricultural extension. These findings suggest that there is a significant need for effective policymaking in the country's agricultural sector and a vital need for investment in educational opportunities. In the paper, we discuss all identified challenges and potential solutions in detail.