Advanced automation has been highlighted as contributory to several accidents involving modern bridge support systems and automation aiding maritime pilots for maneuvering and navigation. This paper argues for reskilling for automation collaboration, that operators need training that provides an understanding of what data the automation uses and how, and to transfer this skill to their working environment and be able to make full use of the automation even under influence of inaccurate data. As a case, this paper explores the predictor automation, which is an advanced navigation aid that visualizes an estimation of the ships future trajectory on an electronic chart display. Field studies and a literature review of maritime accidents were carried out to determine difficulties maritime pilots have with understanding the predictor. This research provides valuable guidance for how automation transparency can be an important part of reskilling and how to achieve it. Copyright (C) 2019. The Authors. Published by Elsevier Ltd. All rights reserved.