Global businesses are transforming towards capturing more value from services, a business model transition called servitization. Digital servitization can help create and maintain a competitive advantage, as well as offering opportunities to tackle major challenges related to environmental pressures and rapidly changing market conditions. This study aims to bridge the gap between the theory of digital servitization and its implementation in the maritime shipping sector. This paper presents a multi-case study that explores the status, perceived challenges, and enablers for the adoption of digital servitization. Empirical data were collected from interviews with 13 companies and analyzed using the PESTEL and DPSIR frameworks. The results are presented across three categories based on the PESTEL framework: organizational context, global priorities, and sustainability. This study contributes to theory by providing empirical insights from the status of digital servitization in the maritime shipping industry. Also, it identifies challenges and needs that can support the transition towards digital servitization and the development of more sustainable solutions. Future research avenues are suggested to advance digital servitization in other industrial sectors.