On August 11, 2020, a confirmed case of coronavirus disease 2019 (COVID-19) in a male correctional facility employee (correctional officer) aged 20 years was reported to the Vermont Department of Health (VDH). On July 28, the correctional officer had multiple brief encounters with six incarcerated or detained persons (IDPs)* while their SARS-CoV-2 test results were pending. The six asymptomatic IDPs arrived from an out-of-state correctional facility on July 28 and were housed in a quarantine unit. In accordance with Vermont Department of Corrections (VDOC) policy for state prisons, nasopharyngeal swabs were collected from the six IDPs on their arrival date and tested for SARS-CoV-2, the virus that causes COVID-19, at the Vermont Department of Health Laboratory, using real-time reverse transcription-polymerase chain reaction (RT-PCR). On July 29, all six IDPs received positive test results. VDH and VDOC conducted a contact tracing investigation† and used video surveillance footage to determine that the correctional officer did not meet VDH's definition of close contact (i.e., being within 6 feet of infectious persons for ≥15 consecutive minutes)§,¶; therefore, he continued to work. At the end of his shift on August 4, he experienced loss of smell and taste, myalgia, runny nose, cough, shortness of breath, headache, loss of appetite, and gastrointestinal symptoms; beginning August 5, he stayed home from work. An August 5 nasopharyngeal specimen tested for SARS-CoV-2 by real-time RT-PCR at a commercial laboratory was reported as positive on August 11; the correctional officer identified two contacts outside of work, neither of whom developed COVID-19. On July 28, seven days preceding his illness onset, the correctional officer had multiple brief exposures to six IDPs who later tested positive for SARS-CoV-2; available data suggests that at least one of the asymptomatic IDPs transmitted SARS-CoV-2 during these brief encounters.