While the growth of financial technologies (FinTech) is making the flow of money faster, easier, and more secure, such technologies are often unable to serve many countries due to the global political environment. Despite its severe impact, this issue has remained understudied in the HCI literature. We address this gap by presenting our findings from a three-month-long ethnography with the Iranian community in Toronto, Canada. We present their struggles in transferring money to and from their home country - a process that entails financial loss, fear, uncertainty, and privacy breaches. We also outline the informal workarounds that allow this community to circumvent these challenges, along with the associated hassles. This paper contributes to broadening the scope of FinTech in the HCI literature by connecting it with the politics surrounding transnational transactions. We discuss the design implications of our findings and their contribution to the broader interests of HCI in mobilities and social justice.