The field of study that this topic is derived from constitutes both federal aviation regulation as well as medical and biological sciences. The compelling idea of this thesis is an in depth investigation of the Federal Aviation Administration's (FAA) regulation and data collection throughout time regarding pilots with Insulin Treated Diabetes Mellitus (ITDM). When in comparison to the continuous evolution of diabetic research and endocrinology in all parts of the world, the regulations regarding this group of pilots seems displaced. This paper explores a chronological order of FAA research and regulations that were conducted on diabetic pilots stemming from 1959 - present. The findings seem to convey that the field of aviation is laden with inconsistencies and misplaced conclusions regarding regulation of insulin-treated diabetic pilots. This paper reflects on the impact of these regulations on this group of pilots from both a biological and medical standpoint as well as from an aviation point of view. In light of advanced medical knowledge, the paper explores what regulations regarding ITDM are in other countries and how FAA regulation should be refined and altered to realign with present day medical knowledge in the United States. This research was conducted to compare the sequential endocrinologic knowledge conducted and the subsequent regulatory actions.