Educators are rapidly switching to remote proctoring and examination software for their testing needs, both due to the COVID-19 pandemic and the expanding virtualization of the education sector. State boards are increasingly utilizing these software for high stakes legal and medical licensing exams. Three key concerns arise with the use of these complex software: exam integrity, exam procedural fairness, and exam-taker security and privacy. We conduct the first technical analysis of each of these concerns through a case study of four primary proctoring suites used in U.S. law school and state attorney licensing exams. We reverse engineer these proctoring suites and find that despite promises of high-security, all their anti-cheating measures can be trivially bypassed and can pose significant user security risks. We evaluate current facial recognition classifiers alongside the classifier used by Examplify, the legal exam proctoring suite with the largest market share, to ascertain their accuracy and determine whether faces with certain skin tones are more readily flagged for cheating. Finally, we offer recommendations to improve the integrity and fairness of the remotely proctored exam experience.