Program evaluation often suffers due to time constraints, imperfect instruments, incomplete data, and the need to report standardized metrics. This article about the evaluation process for the Wi$eUp financial education program showcases the difficulties inherent in evaluation and suggests best practices for assessing program effectiveness. We analyzed the stated behaviors of 125 Wi$eUp survey respondents, finding that debt education produced a greater change in behavior than savings education did but that survey questions related to savings did not reflect the material in the associated module, potentially lowering scores. Longer evaluation periods and better matching of evaluation questions to the content delivered may improve the evaluation process.