In this article, the authors consider the strengths and weaknesses of digital media in the organization of student activism, and how educators can better assist and advise student activists using digital media to create improved learning opportunities. To gain a perspective on the relative strengths and challenges of online media in regard to student activism, they compared contemporary cases of student activism with instances from the 1960s and 1970s era. Specifically, they draw from historical archival research on six cases (three from 1964-1971 and three from 2009-2011) conducted for a History of American Higher Education graduate course at the University of Maryland. They consider the role social media is playing in society as a whole, and how the prevalence of social media influences contemporary activism. Finally, they consider the critical questions higher education educators must consider when advising student activists in a digital age. By exploring implications of the different methods, venues, and technology available to students 40 years ago and today, educators can better support the current generation of students as they learn how to enact change. (Contains 1 table.)