This article considers two digital assignments for courses at The Graduate Center, The City University of New York. In one, students developed digital site reports in the form of individual websites about archaeological sites in the Greco-Roman Near East and Egypt (Art and Archaeology of the Greco-Roman Near East and Egypt, Spring 2013), and in the other (Islamic Art and Architecture, Spring, 2014), students published digital essays about works of Islamic Art for the course website on the CUNY Academic Commons, some of which are in the process of being published on Smarthistory at Khan Academy, which is one of the most popular art history websites in the world. By assigning these projects I sought to support and mentor MA and PhD students to develop a range of digital skills including basic website building and using images in publications and online. I also wanted the students to develop a writing style that enables them to convey their academic findings to the larger public and to value public engagement and scholarship. The possession of strong digital skills is proving vital for young scholars to win grants and jobs in a highly competitive academic environment. This article focuses on the challenges, successes, and failures of integrating digital technology in the teaching of archaeology and art history in order to prepare graduate students to be active and successful contributors in these fields. Appendixes A – G include links to the syllabi, digital project overviews, digital portfolio guide, and grading rubrics that were used in the courses.