Forest industry plays a critical role for many remote rural regions in Nordic countries. Despite the increasing number of various digital transformation initiatives, many forestry organizations still use very traditional non-digitalized work practices in harvesting, logging, and support operations. Unfortunately, digital transformation is often performed as an ad hoc activity without a holistic approach to ensure ICT quality control. In this paper, we aim to answer the research problem of how digital transformation affects the quality of a forest machine operator’s operational processes and service systems. A case study research method with a single case structure was used in this study. The main contribution of the paper is to show that digital transformation shall benefit not only the forest machine operator organization but also their surrounding ecosystem by increasing transparency of operations, reducing travel costs, increasing productivity, and creating a more proactive operating model. Both sociological and technical aspects of digital transformation are discussed in the context of forest service management. Additionally, we show that in order to succeed in digital transformation, forestry organizations must pay attention to various quality aspects holistically: hardware quality, software quality, service quality, data quality, and process/project quality.