Supported by an updated understanding of Online Learning Environments (OLEs) and intelligent Learning Management Systems (iLMSs), the present book aims to explore an innovative landscape, underlining the thinking and the behavior of the LMS users of a public Higher Education Institution (HEI), within the blended-learning context. From a systemic approach, which intelligently combines micro, meso and macro levels of knowledge, the FuzzyQoI model, essentially based on the fundamentals of fuzzy logic and quality of interaction (QoI) of the LMS users, is used as the main methodological option of the present book, revealing a clear opportunity to be used with any LMS Moodle. Moreover, affective-, collaborative- and hybrid-learning are discussed and proposed as future extensions in the field of OLEs. The expectation of this book is to serve as a valuable support for effectively approaching OLEs issues, integrating data analysis and modelling techniques with the identification of users’ profiles, trends and QoI in the field of online education. This array of educational developments could be used as a scaffold, revealing real learner’s educational needs and effective teaching processes.