Guantánamo, and its military commissions, is a place and a legal regime that has captured the imagination of the public, not just in America, but around the globe. Particularly in the legal community, and especially among military lawyers, many are intensely curious about this highly controversial system to try detainees. Over the past three years, I have been asked variations of the same ... [Show full abstract] question by dozens, if not hundreds, of people, including my law students, fellow JAG officers, attorneys, members of the press, friends, and neighbors, namely: “What was Guantánamo like?” or “What were the military commissions like?” or “What was it like defending a detainee?” In this article, I attempt to answer these questions, while at the same time capturing some of the key lessons I learned from my experience as a defense counsel for two detainees. As an aid to those lawyers, both military and civilian, who may have the opportunity to practice before military commissions in the future, I will discuss the most critical lessons I learned from my stint at the Office of Military Commissions-Defense (OMC-D). The article focuses on the practical realities of practicing law at OMC-D and before the military commissions. The article draws most heavily on my experience defending Mohammed Jawad (and, to a lesser extent, Ali Hamza al Bahlul), but also draws from several other cases which have gone to trial or had sig-nificant pretrial litigation. Some of the lessons learned and advice offered herein will be specific to military counsel assigned to OMC-D, but much of it, it is hoped, will be of use to civilian defense attorneys and to lawyers assigned to (OMC-P) and perhaps even to military commission judges. The article should also provide some insight to the general interest reader about this unique legal regime. The article is organized in chronological order from the early phases of being assigned to the Office of Military Commissions and detailed to a case through discovery, pre-trial litigation, and trial.