This book explores the intersection of tutoring and intelligent tutoring systems. The process of tutoring has a long history within learning settings, and this effective method has led to attempts to automate the process via intelligent tutoring system research areas. Intelligent Tutoring Systems (ITS) are increasingly being used in a wide range of educational settings to enhance student learning. They are also used frequently as platforms for research on educational psychology and artificial intelligence. ITS can assess a wide variety of learner characteristics and adapt instruction according to principles of learning. Their effectiveness allegedly derives from their ability to provide detailed guidance to learners and to adapt promptly to individual learner’s needs that are tracked at a fine grained level. Examples of such tutoring technologies include writing environments for guided inquiry learning, environments for collaborative problem solving or discussion, natural language processing and dialogue in tutoring systems, modeling and shaping affective states, interactive simulations of complex systems, ill-defined domains, and adaptive educational games. At their core, these systems rely on our basic knowledge of effective human tutoring. This book starts with a presentation of learning frameworks related to tutoring and ITS. This is followed by examples of best practices of tutoring and learning strategies by implementing within specific ITS. Finally, it presents examples for evaluating the effectiveness of tutoring systems.