This chapter introduces the idea of user-generated dialogueUDialogue technologycontent and describes our experimental exploration aimed at clarifying the mechanism and conditions that makes it workable in practice. One of the attractive points of a speech interface is to provide a vivid sense of interactivity that cannot be achieved with a text interface alone. This study proposes a framework that spoken dialogue systems are separated into content that can be produced and modified by users, and the systems that drive the content, and seek to clarify (1) the requirements of systems that enable the creation of attractive spoken dialogue, and (2) the conditions for the active generation of attractive dialogue content by users, while attempting to establish a method for realizing them. Experiments for validating user dialogue content generation were performed by installing interactive digital signage with a speech interface in public spaces as a dialogue device, and implementing a content generation environment for users via the Internet. The proposed framework is expected to lead to a breakthrough in the spread of using speech technology.