This work addresses the challenges associated with cashless transactions and Mobile Financial Services (MFS) in the Global South. In our 19-months long interview study in Dhaka, Bangladesh, we engaged with 38 participants, including everyday users, bank employees, and policymakers, and investigated their experiences and perspectives associated with financial services. Our findings reveal a wide range of factors, naming intermediaries, terrorist assemblage, and re-skilling the existing employees that impede the mass adoption of cashless transaction services in Bangladesh. The findings from this study contribute to the ongoing discourse on the challenges and opportunities offered by the digitization of financial systems in Bangladesh. Our recommendations aim to improve the integration of the cashless systems within the societal context of Bangladesh and, more broadly, the Global South.