Digital financial services have catalyzed financial inclusion in Africa. Commonly implemented as a mobile wallet service referred to as mobile money (MoMo), the technology provides enormous benefits to its users, some of whom have long been unbanked. While the benefits of mobile money services have largely been documented, the challenges that arise—especially in the interactions between human stakeholders—remain relatively unexplored. In this study, we investigate the practices of mobile money users in their interactions with mobile money agents. We conduct 72 structured interviews in Kenya and Tanzania (n=36 per country). The results show that users and agents design workarounds in response to limitations and challenges that users face within the ecosystem. These include advances or loans from agents, relying on the user-agent relationships in place of legal identification requirements, and altering the intended transaction execution to improve convenience. Overall, the workarounds modify one or more of what we see as the core components of mobile money: the user, the agent, and the transaction itself. The workarounds pose new risks and challenges for users and the overall ecosystem. The results suggest a need for rethinking privacy and security of various components of the ecosystem, as well as policy and regulatory controls to safeguard interactions while ensuring the usability of mobile money.