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Preface Four workshops, two tutorials and two industry-track workshops were held on Monday, June 11th and Tuesday, June 12th in conjunction with 14th International Conference on Intelligent Tutoring Systems (ITS 2018) in Montreal, Canada. The general goal of the workshops was to offer participants an opportunity to engage in professional exchange in an interactive and interpersonal setting. These workshops brought together groups of researchers from around the world who have shared interests. They provided a good, extended opportunity for researchers to get to know each other in a relaxed atmosphere and stimulate the development of ideas and interests, sometimes leading to collaboration, grants and publications. We are pleased to present the proceedings of the following four workshops: • C&C@ITS2018: International Workshop on Context and Culture in Intelligent Tutoring Systems • Learning analytics workshop: Building bridges between the Education and the Computing communities • Exploring Opportunities for Caring Assessments • Optimizing Human Learning: Workshop eliciting Adaptive Sequences for Learning All the workshops were peer-reviewed. We hope the ideas presented in the proceedings provide the springboard for additional research and collaboration. Amruth Kumar and Nathalie Guin, Workshop and Tutorial Chairs