Mobile money, also known as branchless banking, leverages ubiquitous cellular networks to bring much-needed financial services to the unbanked in the developing world. These services are often deployed as smartphone apps, and although marketed as secure, these applications are often not regulated as strictly as traditional banks, leaving doubt about the truth of such claims. In this article, we evaluate these claims and perform the first in-depth measurement analysis of branchless banking applications. We first perform an automated analysis of all 46 known Android mobile money apps across the 246 known mobile money providers from 2015. We then perform a comprehensive manual teardown of the registration, login, and transaction procedures of a diverse 15% of these apps. We uncover pervasive vulnerabilities spanning botched certification validation, do-it-yourself cryptography, and other forms of information leakage that allow an attacker to impersonate legitimate users, modify transactions, and steal financial records. These findings show that the majority of these apps fail to provide the protections needed by financial services. In an expanded re-evaluation one year later, we find that these systems have only marginally improved their security. Additionally, we document our experiences working in this sector for future researchers and provide recommendations to improve the security of this critical ecosystem. Finally, through inspection of providers’ terms of service, we also discover that liability for these problems unfairly rests on the shoulders of the customer, threatening to erode trust in branchless banking and hinder efforts for global financial inclusion.