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Maritime transports play a vital role for several industries in enabling efficient and sustainable transportation of goods. Ports are central hubs in the transport chain since they connect the maritime and land-based transport systems. The central position of ports makes them critical enablers of efficiency through digital connectivity but also implies that they need to consider many types of participating agents with whom they form episodic tight couplings. However, the industry's digitalization level remains relatively low, and we know little of the challenges facing ports in increasing it. Through a case study of digitalization in Swedish small- and medium-sized ports handling different types of cargo and serving different types of transport modes, we identify key objectives and critical challenges underlying digitalization processes in ports.