Digitalization has an impact on all domains of maritime transport and logistics. Ports’ ability to act as a part of digital networks and information chains is vital for its competitiveness. This requires means and prerequisites to integrate with contemporary technology platforms and system architectures. Such readiness should exist in different parallel processes taking place in organizations of port communities. Successful digitalization requires focused technology management ensuring system and data transfer interoperability. The paper addresses problems, obstacles, and hindrances that ports are currently facing in their digitalization efforts. Interoperability and stakeholder interaction is significant, particularly between the port management, municipal ownership, and business operators and vendors. In the contemporary port development, environmental regulations have an effect on the level and effectiveness of digitalization. The future development of port digitalization will be dependent on the port capabilities to adopt and implement reliable and adoptable technologies with clear vision of the future.