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Research has shown that less intensive supervision and fewer conditions for people on probation and parole (a “less is more” approach) can be effective for low-risk supervisees. When these lower-risk individuals receive more intensive supervision and conditions, they tend to have higher rates of failure, which results in a system that is ineffective, inefficient, and costly. The COVID-19 pandemic required most probation and parole agencies to change strategies they used for supervision to facilitate social distancing. This led to an unintentional/unplanned shift toward a “less is more” approach that happens to align more closely with the research. The Bureau of Justice Statistics added a COVID-19 supplement to the 2020 collections of the Annual Parole Survey and Annual Probation Survey. This study explores the quantitative and qualitative responses provided by probation and parole agencies to better understand how and to what extent these agencies changed their practices at the beginning of the pandemic. Results from the quantitative analyses describe changes to: (1) probation population numbers, (2) agencies’ business operations and practices, (3) reporting methods, and (4) drug testing procedures. Additional context about innovative practices and the speed with which changes were required that was described through write-in responses and explanations is included.