In this chapter we propose a departure from classical notion of information systems. We propose to bring in the background of agent’s interaction with physical reality in arriving at a specific information system. The proposals for generalizing the notion of information systems are made from two aspects. In the first aspect, we talk about incorporating relational structures over the value sets from where objects assumes values with respect to a set of attributes. In the second aspect, we introduce interaction with physical reality within the formal definition of information systems, and call them as interactive information systems.