This book constitutes the thoroughly refereed post-conference proceedings of the 5th IFIP WG 13.6 Working Conference on Human Work Interaction Design, HWID 2018, held in Espoo, Finland, in August 2018. The 19 revised and extended full papers presented were carefully selected for inclusion in this volume. The papers deal with the analysis and interaction design of a variety of complex work and life contexts found in different business and application domains. They focus on interaction design for work engagement taking usability of interactive systems to the next level by providing employees pleasurable and meaningful experiences via the tools used at work. The papers are organized in two sections: the first section presents cases of HWID in practice, while the second one focuses on methodological discussion.