Objectives. To describe 4 unique models of operationalizing wastewater-based surveillance (WBS) for severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in jails of graduated sizes and different architectural designs. Methods. We summarize how jails of Cook County, Illinois (average daily population [ADP] 6000); Fulton County, Georgia (ADP 3000); Middlesex County, Massachusetts (ADP 875); and Washington, DC (ADP 1600) initiated WBS between 2020 and 2023. Results. Positive signals for SARS-CoV-2 via WBS can herald a new onset of infections in previously uninfected jail housing units. Challenges implementing WBS included political will and realized value, funding, understanding the building architecture, and the need for details in the findings. Conclusions. WBS has been effective for detecting outbreaks of SARS-CoV-2 in different sized jails, those with both dorm- and cell-based architectural design. Public Health Implications. Given its effectiveness in monitoring SARS-CoV-2, WBS provides a model for population-based surveillance in carceral facilities for future infectious disease outbreaks. (Am J Public Health. 2024;114(11):1232-1241. https://doi.org/10.2105/AJPH.2024.307785).