Autonomous, unmanned ships is on the research agenda in many countries. In 2018 the International Maritime Organization (IMO) added Maritime Autonomous Surface Ships (MASS) to its agenda and started a scoping exercise to find out how the MASS concept would fit into prevailing regulations and conventions. One of the most important international conventions is the rules of the road, the Regulations for Preventing Collisions at Sea, COLREGS for short. These rules are expressed in qualitative terms. The question is whether automatic collision avoidance algorithms will be able to safely interpret words like “early” and “substantial”, or if COLREGS needs to be amended with quantitative specifications? This paper discusses interaction between automatic ships and traditional manned ships in the light of prevailing regulations and new e-Navigation solutions suggested. The paper concludes first, that ship traffic management concepts like “route exchange” and transmission of “intended routes” can be used to coordinate traffic and avoid ships entering into close quarters situations where COLREGS apply. Finally, the concept of “automation transparency” is discussed and a number of concrete examples are suggested.