Why do financial intermediaries persist, despite the promises of disintermediation that accompanied the diffusion of digital technologies?Through a comparative qualitative study of financial intermediation in rural markets in Shan State, Myanmar, and Kerala, India, we map out and make visible official and unofficial roles played by different types of brokers (traders, hundi, transport companies, etc.), and different financial  tools (cash, gold, land, banks, etc.), and look at how information and communication technologies  (ICTs) fit in the interactions between the two. ICTs and human brokers perform functions that are sometimes  complementary, sometimes in conflict, and sometimes simply different from each other. In examining the range of roles that (human and non-human) actors and material practices that are involved in  conducting financial transactions have, we show the central role that historical legacies and politics play in explaining why both cash and financial intermediaries persist in the digital age. Focusing on the different values that human and non-human intermediaries bring to financial encounters helps explain what characteristics make each resilient or replaceable in a time of change, and furthers understanding of which of the many functions embodied by humans can be replaced or supported by digital technologies, and which ones are likely to remain the domain of humans. We conclude that the “expertise” inscribed into technological artifacts such as mobile phones tends to be fixed, whereas human expertise can be more flexible and quicker to react to changing political or economic situations.