Professor Howard teaches both undergraduate and graduate courses at Georgetown University, and he also speaks and runs programs inside of jails and prisons. When possible, he seeks to integrate these two communities, by bringing Georgetown students "inside" to work alongside incarcerated students.

He taught for years at the Jessup Correctional Institution, a maximum-security prison in Maryland, and he now teaches in and directs the Georgetown Prison Scholars Program at the DC Jail.

At Georgetown, at the graduate level, he teaches several Ph.D. seminars, such as "Methodology of Comparative Politics," "Democracy and Democratization," and "Civil Society and Democracy." At the undergraduate level he regularly teaches "Prisons and Punishment," as well as occasional courses on "Democracy" or "Fascism and Extremist Movements." He has also taught a 1-credit "bridge" course for graduating seniors, called "The Forgotten Humanity of Prisoners," held partly at the DC Jail, which included intensive discussions with incarcerated participants in the Scholars Program.

Howard has also taught three different iterations of the non-traditional GOVX 400 "Prison Reform Project" course, which has generated a great deal of media attention. The Spring 2016 version, which included 15 students from Georgetown and 16 from the Jessup Correctional Institution, was featured as the cover story in the Washington Post Sunday MagazineIn the Spring 2017 version, 18 Georgetown students participated in a groundbreaking project to highlight the stories of six returning citizens, and they produced short but powerful documentaries profiling each individual’s struggles and triumphs. The Spring 2018 version focused on wrongful convictions, and it was co-taught by Howard's childhood friend Marty Tankleff, who himself served almost 18 years before being exonerated. The 16 Georgetown undergraduate students took on the cases of 4 wrongfully convicted men who have served a combined total of 96 years in prison for crimes they did not commit. The class itself was covered by Strong Island Films, which is creating and producing a 6-part docu-series called Making an Exoneree, which should air within the next year.