The growing accessibility of digital technology has been met with an increased willingness on the part of scholars to integrate new digital methods into their interpretive and presentational practices. At the same time, the academic assessment structures that support scholarly work have not always been able to keep pace, thus making the pursuit of digital work unreasonable, unless that work is undertaken as additional to the other kinds of scholarship already vetted by any given field or discipline. Five College Digital Humanities (5CollDH) has turned to the question of assessment because we have come to understand that we cannot rightfully focus on cultivating digital scholarly innovation if we are not equally attentive to the kinds of curricular, financial, and administrative structures that make new kinds of work possible. This report focuses on the challenges and moves toward solutions to some of the pervasive problems attached to assessing the work of scholars doing digital work in academic institutions.