One of the biggest unaddressed challenges for the digital economy is what to do when electronic transactions go wrong. Consumers are frustrated by interminable phone menus, and long delays to problem resolution. Businesses are frustrated by the high cost of providing quality customer service. We believe that many simple problems, such as mistyped numbers or lost orders, could be easily diagnosed if users were supplied with end-user debugging tools, analogous to tools for software debugging. These tools can show the history of actions and data, and provide assistance for keeping track of and testing hypotheses. These tools would benefit not only users, but businesses as well by decreasing the need for customer service. Categories and Subject Descriptors H.5.4 [Information Interfaces and Presentation]: Hypertext/Hypermedia – user issues General Terms: Human Factors