It is usually a straightforward tax question: Is an advance of capital to a business debt or equity? But in some cases the question gets harder to answer, mostly because of the tangled multifactor test we use. Long ago, most tax practitioners gave up trying to clean up the process of answering hard debt-equity questions. But recent developments show the Service, practitioners, and courts moving towards a simpler way to decide these cases in the form of a single question: Did the parties to the transaction reasonably expect the funds would be repaid in full? This Article discusses the development of recent debt-equity case law on structured financing arrangements including Pritired, Castle Harbour, Hewlett-Packard, Schering-Plough, PepsiCo, and the Scottish Power cases.