The impact of technology on the humanities, arts, and social sciences (HASS) is already profound and will only escalate as time goes on. The challenge that HASS scholars face is: will they create the world they are in the process of entering or is this world going to be created for and imposed on them? If the latter, progress in HASS will certainly be impeded; if the former, then cyberinfrastructure in the HASS will be created in the image of those who best understand what they require. This article explores the question of how cyberinfrastructure for the HASS might facilitate the development of digital technologies and applications that will meet the specialized needs of scholarship. Formidable barriers that exist are discussed—especially those peculiar to humanities and social sciences—that impede the development of specialized technologies and applications. Also addressed is the interplay between various players directly involved with developing specialized technologies and applications tailored for the HASS. Finally, changes in academic perspective are discussed that may result in transformations in cyberinfrastructure to improve the likelihood of success in creating specialized technologies and applications. The authors’ observations are based primarily on lessons learned in the development and deployment of the InscriptiFact Image Database along with experiences with InscriptiFact’s sister archival imaging project, the West Semitic Research Project, both at the University of Southern California.