Techniques are described herein that are capable of estimating a result of configuration change(s) in an enterprise. Enterprise information regarding a designated enterprise is gathered. The enterprise information is combined with anonymized information that is received from multiple enterprises to provide combined information. An actual impact of configuration changes in at least one enterprise (e.g., with regard to a first subset of the machines therein) is determined and/or a predictive impact of the configuration change(s) in at least one enterprise (e.g., with regard to a second subset of machines therein) is inferred. An estimate of a net financial result of implementing the configuration change(s) (e.g., with regard to the second subset of the machines) in the designated enterprise is generated based at least in part on the actual impact and/or the predictive impact.