A modern ship bridge is becoming increasingly digitalized, featuring multiple screen-based control systems and advanced automation. As with other industries that have gone through the transformation from analogue to digital control, computerization tend to improve overall safety but at the same time introduce new challenges. One such challenge is related to human-machine teamwork. In the maritime area the quality of this teamwork relies among other things on operators being able to make sense of the information that is being presented to them about the status and behaviour of the vessel, its control systems, as well as the potential threats to its capability. Dynamic Positioning (DP) is an example of a highly automated system where a number of unwanted situations has occurred, and where weaknesses in this teamwork has been identified as a major contributing factor. In this paper we explore Human Machine Interface (HMI) and training measures for improving the safety of such operations by strengthening the operators' ability to recognise and handle unexpected events.