New York State has a county system of probation services that consists of 58 departments. Although probation is administered locally, the State Division of Probation and Correctional Alternatives (DPCA) is responsible for regulating and assisting the departments and reimbursing some of their costs. The data used in the current study to create a measure of supervision strategies for New York's probation departments came from the New York State Probation Outcomes Project (NYSPOP). The NYSPOP is a long-term effort to develop outcome measures for probation and to use these outcomes in requesting resources and managing practices. The supervision measure used in this study was derived from a statewide survey of probation goals administered in 1998 to probation officers, except in New York City. In reviewing the means of measuring each variable used in this study, this article begins with the dependent variable (supervision) and works back through punitiveness to county crime and political views and finally to the county demographic variables. This study had a moderate, but acceptable, level of success in measuring the supervision strategies of probation departments. Departments do vary on supervision preferences. Contrary to the expectations derived from the literature, probation supervision strategy does not vary with the relative size of age groups, unemployment, political liberalism, or punitiveness at sentencing. Racial diversity does have an effect on supervision, showing the expected tendency toward enforcement; however, the effect of this variable and all variables collectively is small, and the total variation in supervision that can be explained by environmental forces is negligible. The findings may suggest that probation departments do respond to the environment in appropriate ways but that the processes of alignment are too complex to be properly represented in current thinking about probation supervision policy and the theoretical models that are based on it. 2 tables and 18 references