In the past two decades, the digitization of humanities resources has rapidly expanded, giving rise to the field of Digital Humanities (DH). This evolution has fostered a growing need for effective interoperability—the ability to access and integrate data across diverse digital collections, tools, and platforms. Despite significant technological advancements and the development of standards aimed at facilitating interoperability, challenges persist. These challenges are not only technical but are also influenced by sociocultural factors, which include organizational and cultural elements. This paper aims to bridge the gap in the literature concerning these sociotechnical factors affecting interoperability within DH projects and collections.This paper presents the analysis of the real‐world experiences of DH researchers attempting to connect material from different sources. Each participant described a specific incident where combining software or content was particularly problematic. This data was analyzed via thematic analysis. The findings reveal a complex landscape of interoperability challenges, underpinned by a range of sociotechnical factors. These factors include, but are not limited to, discrepancies in metadata standards, differences in organizational cultures, and varying levels of technical expertise among practitioners. By highlighting these factors, the paper contributes valuable insights into the multifaceted nature of interoperability issues in DH, offering evidence‐based plans to address these challenges.