We assess the potential of digital technologies in supporting business activity in underserved regions by investigating the responses of small entrepreneurs in those regions to variations in the mode of provision of digital business training programs. Specifically, we analyze and compare how learning and practice adoption are affected by three distinct provision modes of the same program content: a static training module without any sort of interaction; an interactive training module that involves engaging with automated chatbots; and an interactive module that combines interactions with automated chatbots and human agents. To empirically gauge the effectiveness of each mode of provision, our study encompasses data from a four-arm randomized controlled trial involving 461 small entrepreneurs from Brazilian underserved regions, who participated in a real-world training program on financial literacy during July 2022. We fail to detect a significant effect of the online training, either on its own or complemented by human or chat-based support. In fact, we observe a negative effect of the training on participants’ learning of financial practices when interactions occurred exclusively with the chatbot. Our extension analyses indicate that these negative effects depend on participants’ level of digital literacy, which affects their ability to engage effectively with the online application. Furthermore, the treatment involving human support is also subject to the level of engagement of the entrepreneurs and yielded negative effects on sales among less attentive participants. Overall, our study questions the effectiveness of digital technologies in supporting business activity in underserved regions. We propose that, even though these tools may potentially increase access for entrepreneurs in such areas, there are significant constraints and vulnerabilities that undermine their ability to fully harness the benefits of such initiatives. Hence, in such contexts, the use of digital technologies should be approached with caution.