Rapidly evolving needs of shippers, rising competition, advancement in digital technologies and a quest to increase cost and operational efficiencies are all driving the digital transformation of maritime logistics. However, in contrast to other industries such as media, telecom, banking, retail and even other traffic modes, the often family-controlled and network-centric liner shipping industry has historically been conservative in adopting innovations; hence, it is still far behind in embracing digitalization. Based on semi-structured interviews with senior executives of liner shipping companies, this study explores the current digital maturity levels, the opportunities provided by digitalization and the underlying challenges that hinder its implementation in the liner shipping segment within the larger maritime logistics industry and identifies the essential leading strategies of digitalization in this segment. The digital maturity categories applied to liner shipping provide an opportunity for practitioners in this industry to evaluate their business functions’ digital maturity levels. Furthermore, based on interview data, digital transformation for the maritime logistics industry is defined, as well as 9 major barriers and 19 different pathways to digital transformation are identified. Understanding the key challenges and success factors in the industry is a key to approaching digitalization problems and developing a healthy digital transformation process. © 2022 The Authors