This book constitutes the proceedings of the 16th International Workshop on Knowledge Management and Acquisition for Intelligent Systems, PKAW 2019, held in Cuvu, Fiji, in August 2019. The 9 full papers and 7 short papers included in this volume were carefully reviewed and selected from 38 initial submissions. The papers cover advanced research work that contributes to the technical and theoretical aspects in the fields of intelligent systems/agents, natural language processing, and applications of machine learning techniques including Deep Learning to real world problems.