The ability to handle maritime operations is increasingly dependent on control systems. Such systems play a crucial role in critical situations, by presenting safety-critical information that allows operators to make sense of the situation, i.e. sensemaking. Rules and regulations influence design of the systems and training, both key areas impacting safety. This paper is based on regulations in Norway related to design, operation and training of maritime operations involving dynamic positioning (DP) and navigation systems used on the bridge. We have explored accident reports, observed work, performed literature review and interviewed actors (regulators, designers, seafarers, and certification agencies) to get a sound basis for our suggestions. We find that rules are improving slowly and that there is little focus on Human Factors (HF) design from basic ergonomics through support of cognition. Totality of rules has not been adopted to support sensemaking. Technology driven implementation may not support critical tasks and the users can be subjected to stress, poor sensemaking and conditions leading to accidents. Our suggestion is to support functional regulation, focus on HF from design, use critical "safety-cases" and verify training periodically.