Given the growing importance of the digital economy, its measurement is essential for evidence-based policymaking, effective decision-making, and monitoring economic transformation. This study aims to identify and analyze the challenges of measuring the digital economy in Iran, with particular attention to local conditions. An exploratory qualitative approach based on thematic analysis was employed. Initially, challenges were identified through a review of the literature, official documents, and reports. Subsequently, the perspectives of experts from academia, industry, the private sector, and governance institutions were collected and analyzed through semi-structured interviews and two expert panels involving a total of 21 participants. The findings indicate that the challenges of measuring the digital economy in Iran can be classified into five interrelated categories: conceptual challenges; data and statistical challenges; methodological and computational challenges; challenges related to indicators and national accounts; and structural challenges of the digital economy. The results further suggest that the manifestation and intensity of these challenges in Iran differ from those reported in many other countries. In addition, the identification of challenges related to selecting an appropriate price basis for estimating the digital economy’s share and the ambiguity arising from the use of Gross National Product instead of Gross Domestic Product emerged as key findings and distinctive contributions of the study.