Ensuring that software systems evolve in a desired manner has thus far been an elusive goal. In a continuing effort towards this objective, in this paper we propose a new approach that monitors an evolving software system, or its evolution process, against evolutionary policies so that any feedback obtained can be used to improve the system or its process. Two key concepts that make this possible are: (1) a mechanism to detect policy violations and (2) a contextual framework to support activities of evolving a software system beyond the next release. Together, they could provide a wide and deep scope for managing software evolution. The benefit of our approach is that it would help in: sustaining the quality of a software system as it evolves, reducing evolutionary costs, and improving evolutionary processes.