There is a global trend of automation of container terminals. However, there is a lack of literature to guide automation projects for brownfield terminals. Therefore, the experiences and lessons learnt from historical brownfield automation of container terminals are a valuable source of information to guide future projects. This paper describes the brownfield container terminal automation projects carried out in recent years. For each project, the drivers, challenges, benefits, and drawbacks of automation were gathered using a questionnaire directed to operators of brownfield converted container terminals. The characteristics as to the terminal sizes and implemented solutions were gathered via a desk study. It was found that the main drivers for automation are operational cost reductions and higher productivity. However, the desired levels are not always reached and depend on the terminal conditions and the solutions adopted. The continuity of operations was also identified as a major challenge. Terminals have dealt with it either by following a phased, greenfield-like, or big bang approach. Most terminals have opted for semi-automated solutions (automation of yard equipment only); this resulted in fewer labor problems, improved vessel productivity, less required space, and better agility in dealing with disruptions. Most terminals have chosen either automated RMG or the automated version of their manned equipment for yard operations, although exceptions were observed.