The income of smallholder coffee farmers can be increased by optimizing the added value of the product through increased entrepreneurial capacity. Coffee farmers need to adopt innovations and new approaches that are more sustainable with organic farming systems. East Java region is the largest coffee producer in Java island, fourth in Indonesia, and has an important contribution in coffee exports which is 24.4% of the national coffee export. The purpose of this study were to identify differences in characteristics, support of government extension services, private extension agents, and environmental support for smallholder coffee farmers and to analyze the effect of characteristics, government extension services, private extension agents, and environmental support on the entrepreneurial capacity of smallholder coffee farmers. This study were carried out at Arabica coffee farms in Bondowoso Regency and Robusta coffee farms in Malang Regency, East Java from August to October 2019. The survey method was used in this research. Data were collected through interviews with questionnaires in a total of 376 smallholder coffee farmers. Data were analyzed using descriptive (SPSS) and inferential statistics (structural equation model/SEM analysis using Smart PLS). The results of research showed that non formal education and roles of private extension agents were found to be low. This low value of non-formal education attended by farmer was affected by the low intensity of training program, field school, and courses for farmers. Moreover, motivation, government extension support, environmental support, and entrepreneurial capacity of smallholder coffee farmers were categorized as moderate. Factors significantly influenced entrepreneurial capacity of coffee farmers included: characteristics of farmers, government extension support, roles of private extension agents, and environmental support. The role of government to strengthen private extension agents was possible through partnership between coffee farmers, government and exporter or private sectors. The motivation in business development, the use of conventional mass media by smallholder coffee farmers and the role of motivators of private extension workers for coffee farmers in Bondowoso regency were higher than in Malang regency.