Many port-cities around the world have presented ambitious port expansion plans to bridge the infrastructure gap as a way to gear up their economies. At the same time, many ports are troubled by heavy congestion, labour disputes, scarcity of land, negative public opinion, environmental degradation and a fight for talent. Existing models of problem solving and solution design start from a bargaining position, which usually ends up in a trade-off. The value of paradox thinking lies in the acknowledgement that problems are surrounded with ambiguity. Such a mind-set can trigger creativity, out-of-the box thinking, organisational learning and co-operation which can resolve complicated issues. What paradoxes are we facing in the port landscape and how can this creative tension trigger renewal and innovation?