In the rapidly evolving world of software development, maintaining user satisfaction and adapting to changing needs is critical to the success of software products. This tutorial paper focuses on a data-driven approach to user review and contextual analysis as a means to monitor software maintenance and evolution and ultimately improve user satisfaction. To leverage user feedback to support software evolution, we organize the tutorial in three parts: 1) evaluating collective user expectations and perceived quality; 2) monitoring user satisfaction across software updates; and 3) incorporating user profiles and situational contexts into the analysis. This tutorial aims to provide researchers, IT professionals, and developers with the approaches necessary for adaptive and responsive software evolution.