Background Prevention through Intervention is a community paramedicine program developed by Birmingham Fire and Rescue Services in Alabama. This program aims to reduce dependency on emergency medical services (EMS) for nonemergency-related events through education and to lower the frequency of emergency calls in underserved populations. A telehealth intervention with an emphasis on hypoglycemia was implemented to (1) tailor the intervention to meet the educational needs of participants and (2) facilitate follow-ups. A pre-post pilot feasibility evaluation of the telehealth intervention was conducted. Objective This paper describes the results of the feasibility evaluation, implementation challenges, and the lessons learned about the deployment of a hypoglycemia prevention program in an underserved area and its evaluation. Methods This single-arm pretest-posttest intervention included (1) an initial in-person visit (week 1), (2) 3 weekly telecoaching calls (weeks 2-4), (3) 1 biweekly call (week 6), and (4) a final in-person visit (week 8) for collecting posttest data from individuals who called EMS due to hypoglycemic events. In-person visits included educational sessions conducted by EMS personnel. Participants’ education included tailored content related to hypoglycemia. Weekly telecoaching calls focused on hypoglycemia symptom monitoring and education reinforcement via a telehealth dashboard. The primary measures focused on feasibility measures, and exploratory measures focused on the fear of hypoglycemia, self-efficacy, and a knowledge of diabetes. Results A total of 40 participants participated in the intervention. However, the study was marred with high attrition. The various factors behind the low retention rate were discussed. There was a decreasing trend in all three subdomains of the fear of hypoglycemia from pretest to posttest. There was also a significant increase in participants’ self-efficacy in hypoglycemia self-management (P=.03). Conclusions This study shows preliminary and promising results for a community-based intervention specifically for hypoglycemia. However, the socioeconomic setting in which the intervention was delivered may have resulted in high dropout rates and low attendance during the intervention, which are considerations for future telehealth studies. Trial Registration ClinicalTrials.gov NCT03665870; https://clinicaltrials.gov/ct2/show/NCT03665870