While shipping large and heavy cargo like jack-up rigs or semi-submersibles, the Motion Monitoring and Captain Decision Support system is a valuable tool to ensure a safe and economical voyage. Using the dynamic characteristics of the vessel, in combination with 5-day weather forecasts and design limits like maximum accelerations at the cargo location, roll motion and/or leg bending moments, more and better information is available to the Master to choose safe route, heading and speed. This way the best knowledge of what to expect is contributing to the safety of cargo, vessel and crew. The Octopus onboard system gathers a large amount of information about ship position, speed, heading, nowcast weather data and corresponding ship motion data. Reference is made to the paper of Peters [2] for background information of the Octopus Motion Monitoring and Decision Support system and an overview of methods used by the motion measurement system. In May 2008 the first Dockwise vessel started to gather weather and ship motion data. It is estimated that each vessel gathers around 50.000 nautical miles of data in a year, which is all collected in a database. The paper presents how this information is used for general research to environmental data, ship motion data and comparison to design values. Scatter diagrams from nowcast weather data can be produced. After collecting a certain amount of measurements, so called Dockwise scatter diagrams could be used as input for future voyage calculations. With this engineering approach Masters decisions for weather routing and bad weather avoidance is taken into account. This could lead for example to reduced design wave for a passage around the Cape of Good Hope. Now casted weather data and ship motions data is compared to design values from the cargo securing manual. Statistics like maximum difference, average difference give extensive data and insight in the operational margin of Dockwise transports. The calculation of the operational margin is independent of the standard safety margin valid for each transport. The conclusion is that the recorded nowcast significant wave height for the analyzed voyages never exceeded 5.0 [m]. With larger design wave heights the minimum operational margin increases to more than 40%, while the lowest operational margin occurs at design wave heights around 4.5 [m]. The database built by gathering all relevant information from the system and from crew observations, increases insight in the operational margins, which contributes to increased knowledge and safety.