AbstractA museum's digital archive system gathers information about cultural heritage and makes it accessible to the public. In this study we clarify the extent to which search behaviors reflect task outcome and foster users’ knowledge of painting and calligraphy. Ten users participated who are special interest museum visitors. They joined in this evaluation of the Digital Archives of Chinese Painting and Calligraphy Search System (DA‐PCSS) of the National Palace Museum in Taiwan. Participants’ search activities and interactions with the DA‐PCSS were recorded in two simulated tasks. The results show that the high‐performance (HP) group who received high scores for their essays on the tasks formulated precise and relevant queries. Furthermore, the HP group were able to find information needed inside or outside the system to explore and synthesize the information, which was clearly reflected in their search move patterns, during the search process. Our results suggest that the criteria for learning at various stages of search suggested by Vakkari (2016) seem to validly reflect the quality of the search outcomes. In all, the results elucidate how the evaluated system supports users as they search for target items, as well as how learning occurs during the search process and in turn influences task outcomes.