A system is built to serve a common purpose of an organization or a network; it usually consists of a set of operations, interfaces for inputs and outputs, and a group of users with direct or indirect interactions. Systems exist in nature as well as in virtually any conceivable area of human society (Dori, 2003). We are surrounded by systems which undergo changes over time and experience some sort of evolutionary pressure. In order to formulate a system with its specifications, a complete set of updated requirements is established before delving further into the development process. Here the presumption is that, based on the specified requirements, the system would adequately serve the underlying community within its predefined life cycle. However, like any other objects or materials, the system will gradually become outdated over an extended period of time (unless any newly emerged requirements are addressed); this is due to the changes in its surrounding environment, which includes end users, groups of people involved through meetings or other common interests, their mutual interactions with other systems or exchange of information through social networks, related auxiliary or dependent systems and its type of services to the community. In the end, the system will lose its value over a period of time and it is a common fact, but unavoidable scenario, unless explicit measures are taken for re-configuring the system with new specifications. In other words, the current expiring features need to be replaced with newly emerged requirements so that it can maintain its efficacy and remain competitive in the market. Traditional systems do not have such capabilities to address emerging requirements. These systems either need to be thoroughly re-engineered, or simply replaced with a new system. Both of these options are very expensive in all aspects. With the help of a “Wrapper system,” if a system can identify these upcoming requirements and able to direct necessary changes into the system itself by dynamically adjusting its specifications, then it will be in a good standing to extend its life cycle, and maintain a higher level of user satisfaction through its dynamic configurations. A wrapper system is a real-time system itself; it is a carefully formulated meta-structure to address dynamic configurability. In this setup, the target system can be termed an “Evolvable system” which, via its adaptability, gradually makes a valuable return of investment over an extended software lifetime.