The engineering community has long recognized the need for adequate maintenance of drainage structures. However, despite several regional and national studies that highlight the damaging effects of poor maintenance, few agencies have improved their inspection and maintenance schedules. Although inadequate funding is the most plausible reason for this scenario, the lack of formal procedures to survey drainage assets, determine their conditions vis-à-vis their functional objectives, and objectively quantify their condition also adds to the problem. Described is a practical prototype maintenance quality assurance (QA) procedure for evaluating the adequacy of drainage asset maintenance in a consistent manner. Key components of the QA procedure are discussed in detail. A software program developed to implement the various components of the QA procedure is described. The program is a simple tool with which to check the condition and functionality of drainage assets at any time. Designed to handle both surface and subsurface drainage assets, the program can be implemented at any level of maintenance jurisdiction. A complete description of the program’s functionality, from the selection of inspection units to the generation of maintenance quality ratings, is provided. Implementing the presented concepts could result in a substantial economic benefit for the implementing agency.