Shipping, like most industries, is undergoing a digital transformation process which influences existing business models and operational practices, in a multifaceted way. Today, the shipping business context has been changing to incorporate further social demands, environmental, innovation and sustainability priorities, into fundamental shipping strategies, while taking advantage of technological advancements. In the era of Industry 4.0, which constitutes a recent evolution of advanced communications and information technologies and further promotes sustainable, human-centric, and resilient business development strategies, shipping and port entities need to embrace a broader perspective and a deeper understanding of various elemental technologies, namely: Artificial Intelligence, Blockchain, Cloud Computing, Big Data, and Physical Internet, in addition to core maritime logistics matters. This chapter proposes a descriptive framework of shipping digitalization and port automation, while providing a review of related technologies and business approaches, also international initiatives, for automation in global ports. Hence the chapter offers insights for business practitioners to steer through the current challenging global environment, also for policy makers to gain a more informed understanding of maritime logistics developments, towards necessary coordination and oversight mechanisms implementation.