Introduction: Goodwill is slippery, and many interdisciplinary approaches require coordination. While it still represents a problem for accountants, its economic valuation is often flawed by inconsistent appraisal of its expected value. This valuation is even more important when evaluating digital goodwill. Justification: This research is justified by the growing importance of digitalization, which concerns not only digitally native firms but also evolving “brick-and-mortar” companies. Objectives: This study aims to provide an analogic application of traditional goodwill valuation patterns to digitized businesses. Methodology: The research methods consider a comparative analysis with traditional valuation approaches, then extend to digital applications. Results: Empirical analysis using “with-or-without” differential approaches shows the incremental value of digital solutions and their impact on goodwill. Limitations of the study: This preliminary study does not consider artificial intelligence or machine learning applications where digitized ecosystems evolve following self-learning patterns. Networked ecosystems ignited by scalable digitalization are also not considered, albeit deserving further investigation.