In the new course of study starting next year, programming education starts in all elementary schools in Japan. However, the definition of programming education is not so clear, and an independent compulsory subject for programming education is not available, yet. Almost all of the teachers are not good at programming; they do not have enough ideas on how to teach “programming” in ordinary required subjects. It is expected, however, that this new engagement on programming education at elementary school will promote the development of new ways of teaching programming education in junior and senior high schools. The authors developed a new client-server web system that can help teachers teach Python programming and also help gifted and talented students learn by themselves. In this chapter, the authors detail such a client-server Web system and the activities performed at a juku (private tutoring) school.