Context Primary care physicians need a strong foundation in diabetes management, as they are the first line of care for patients with this complex disease, which is increasing in frequency in the United States. This foundational training begins in medical school, but its applications become more important during residency. Objectives To quantify osteopathic and allopathic family medicine residents’ amount of exposure to diabetes in residency training, investigate referral patterns related to diabetes management, and assess comfort levels with various diabetes treatment modalities. Methods An 18-item cross sectional survey was sent via email using Qualtrics to program directors and chief residents of 16 different training programs located in seven different health systems and four different states; the programs were focused on family medicine, internal medicine, pediatrics, and combined internal medicine/pediatrics programs. The link was also posted on Twitter using specific “handles” to “tag” professional associations and groups related to primary care. Emails and tweets were initiated on October 15, 2018 and responses were collected through April 15, 2019. Data collection was reinitiated via email only from May 1, 2020 through July 31, 2020 due to low initial response rate. The study, which included multiple choice and Likert scale questions with some skip logic, was designed by study investigators. Data was exported from Qualtrics to an Excel spreadsheet and analyzed using descriptive statistics, which are reported as percentages. Results A total of 61 residents responded to the survey, with most (52; 85.2%) enrolled in family medicine or internal medicine programs. Residents were mostly located in rural (28; 45.9%) and suburban (25; 41.0%) areas. Respondents reported being extremely comfortable with metformin (45; 73.8%), basal insulin (24; 39.3%), and healthy lifestyle education (32; 52.5%) for the treatment of diabetes. They reported being least comfortable with diabetes technology, with 51 (83.6%) uncomfortable or extremely uncomfortable with insulin pumps and 43 (70.5%) uncomfortable with continuous glucose monitoring systems for diabetes treatment. Referral rates to endocrinologists were low, with 47 (77%) reporting referral of diabetes patients 10–15% of the time. Residents reported interest in workshops and online continuing medical education for further training opportunities, but interest in additional formal training was low (3; 4.9%). Conclusions Residents in this study reported confidence in diabetes management and referral rates among this group were low. However, reported comfort levels with treatment modalities beyond metformin and lifestyle changes were not strong. Referral rates may have been low due to the low number of endocrinologists in rural areas and therapeutic inertia. Diabetes fellowships could increase resource availability for patient referral. Utilization of diabetologists in primary care programs may also add benefit and improve skills among trainees including more familiarity with diabetes technology and use of newer medications used in diabetes management.