More than 1.2 million adults are incarcerated in the United States and hence, require health care from prison systems. The current delivery of care to incarcerated individualss is expensive, logistically challenging, risk fragmenting care, and pose security risks. The purpose of this study was to evaluate the association of patient characteristics and experiences with the perceived telemedicine experiences of incarcerated individuals during the pandemic. We conducted a cross-sectional study of incarcerated individuals in 55 North Carolina prison facilities seeking medical specialty care via telemedicine. Data collection took place from June 1, 2020 to November 30, 2020. Of the 482 patient surveys completed, 424 (88%) were male, 257 (53.3%) were over 50 years of age, and 225 (46.7%) were Black or African American and 195 (40.5%) were White, and 289 (60%) no prior telemedicine experience. There were 3 strong predictors of how patients rated their telemedicine experience: personal comfort with telemedicine (P-value < .001), wait time (P-value < .001), and the clarity of the treatment explanation by the provider (P-value < .001). There was a relationship between telemedicine experiences and how patient rated their experience. Also, patients who were less satisfied with using telemedicine indicated their preference for an in-clinic visit for their next appointment