This chapter sets out a foundation for the management of software maintenance. The foundation highlights a fundamental for managing software maintenance effectively—recognition of the connection between managing change in organizations and the organizations’ health and fitness. The changes arising as a consequence of software maintenance nearly always impair or improve that health and fitness. The basis for that impact lies in how business rules contribute to the performance of systems, and in how systems contribute to the performance of organizations. An understanding and application of how changes from software maintenance on business rules and systems affect the performance of organizations provides a basis for management action. With that added confidence, managers can reduce impairing their organizations’ health and fitness and can increase positive action to improve their organizations’ health and fitness via software maintenance.