This book constitutes the thoroughly refereed post-conference proceedings of the JSAI-isAI 2016 Workshops, LENLS 13, HAT-MASH, AI-Biz, JURISIN and SKL, held in Kanagawa, Japan, in November 1016. The 22 regular papers presented in this volume were carefully reviewed and selected from 64 submissions. LENLS 13 was the 13th event in the series, and it focused on the formal and theoretical aspects of natural language. LENLS (Logic and Engineering of Natural Language Semantics) is an annual international workshop recognized internationally in the formal syntax-semantics-pragmatics community. It has been bringing together fordiscussion and interdisciplinary communication researchers working on formal theories of natural language syntax, semantics and pragmatics, (formal) philosophy, artificial intelligence and computational linguistics. HAT-MASH 2016 (Healthy Aging Tech mashup service, data and people) was the second international workshop bridges healthy aging and elderly caretechnology, information technology and service engineering. The main objective of this workshop was to provide a forum to discuss important research questions and practical challenges in healthy aging and elderly care support to promote transdisciplinary approaches. AI-Biz 2016 (Artificial Intelligence of and for Business) was the first workshop held to foster the concepts and techniques of Business Intelligence (BI) in Artificial Intelligence. BI should include such cutting-edge techniques as data science, agent-based modelling, complex adaptive systems, and IoT. The main purpose of this workshop is to provide a forum to discuss important research questions and practical challenges in Business Intelligence, Business Informatics, Data Analysis and Agent-based Modelling to exchange latest results, to join efforts in solving the common challenges. JURISIN 2016 was the tenth international workshop on Juris-informatics. Juris-informatics is a new research area which studies legal issues from the perspective of informatics. The purpose of this workshop was to discuss both the fundamental and practical issues among people from the various backgrounds such as law, social science, information and intelligent technology, logic and philosophy, including the conventional AI and law area. SKL 2016 (The Third International Workshop on Skill Science) was aimed to internationalize the research on skill sciences through organizing the meeting. Human skills involve well-attuned perception and fine motor control, often accompanied by thoughtful planning. The involvement of body, environment, and tools mediating them makes the study of skills unique among researches of human intelligence.