The purpose of this research is to identify and categorize challenges inherent in digital work initiatives, with a particular focus on robotic process automation (RPA). The study began with the development of a conceptual framework to emphasize significant themes and propositions concerning RPA implementation, based on a review of existing literature. The proposed framework underwent a rigorous validation process using qualitative data gathered through an in-depth case study analysis. Data collection methods included interviews with IT experts in RPA solutions, which provided insights into the challenges they encountered. The analysis identified five distinct themes: organizational, technological, human, process, and data. Notably, the framework differed from the feedback of one interviewee, who proposed a new theme focused on data challenges, including low availability of digital data, low data quality, and unstructured data formats. The study identified eighteen challenges categorized under the aforementioned themes, making it highly relevant to RPA theory and practice.