An important step to achieve greater financial inclusion is to increase the acceptance and usage of digital payments. Although consumer adoption of digital payments has improved dramatically globally, the acceptance and usage of digital payments for micro, small, and medium retailers (MSMRs) remain challenging. Using random forest estimation, we identify 14 key predictors out of 190 variables with the largest predictive power for MSMR adoption and usage of digital payments. Using conditional inference trees, we study the importance of sequencing and interactions of various factors such as public sector initiatives, technological advancements, and private sector incentives. We find that in countries with low POS terminal adoption, killer applications such as mobile phone payment apps increase the likelihood of P2B digital transactions. We also find the likelihood of digital P2B payments at MSMRs increases when MSMRs pay their employees and suppliers digitally. The level of ownership of basic financial accounts by consumers and the size of the shadow economy are also important predictors of greater adoption and usage of digital payments. Using causal forest estimation, we find a positive and economically significant marginal effect for merchant and consumer fiscal incentives on POS terminal adoption on average. When countries implement financial inclusion initiatives, POS terminal adoption increases significantly and MSMRs’ share of P2B digital payments also increases. Merchant and consumer fiscal incentives also increase MSMRs’ share of P2B electronic payments.