This paper reports on a co-speculative interview study with charitable donors to explore the future of programmable, conditional and data-driven donations. Responding to the rapid emergence of blockchain-based and AI-supported financial technologies, we specifically examine the potential of automated, third-party 'escrows', where donations are held before they are released or returned based on specified rules and conditions. To explore this we conducted pilot workshops with 9 participants and an interview study in which 14 further participants were asked about their experiences of donating money, and invited to co-speculate on a service for programmable giving. The study elicited how data-driven conditionality and automation could be leveraged to create novel donor experiences, however also illustrated the inherent tensions and challenges involved in giving programmatically. Reflecting on these findings, our paper contributes implications both for the design of programmable aid platforms, and the design of escrow-based financial services in general. CCS CONCEPTS • Human-centered computing → User studies.