The paper introduces an Internet of Tings (IoT) Robot simulator. The aim of this simulator is to discuss issues for Context-Oriented Programming. The context-sensitive and live- adaptive are important features for next-generation systems such as IoT and Industrial 4.0. Context-Oriented Programming (COP) Languages give us adequate modularity to implement those features. However, even if we construct a program on COP, we cannot predict enough for its behavior. We consider a thinking way of Operating Systems (OS) would be helpful to overcome this problem. In OS, researchers have proposed communication algorithms based on some common problems, such as the five philosophers’ problem. Towards finding typical problems of COP such as the five philosophers’ problem, we propose a simple cooperative robot system simulator. The novel mechanism of this system is that the one and same COP program drive a cooperative robot on both a virtual map and real worlds. We expect the mechanism contributes to imagine realistic issues of context- oriented software for constructing next generation robots. The paper presents a mechanism for this simulator system and shows the simulator finds some issues of context-oriented software.