In this chapter, we discuss challenges in applications of communication robots. A communication robot is a robot that communicates with people in the way people normally do with each other. To date, there is no actual deployment of communication robots, hence researchers have been actively conducting demonstrative field trials to seek a potential role of such robots, and investigate people’s acceptance of them. As an example, we introduce one of our own field trials, which was conducted in a shopping mall where a robot provides route and shop information while attempting to build rapport with repeated visitors. Building on this example, we further discuss the future challenges of the application of human-robot interaction.