Behavioral skills training (BST) is often used to train caregivers to implement various behavior management procedures; however, additional strategies are sometimes required to promote the generalization of skills from a contrived setting to the natural environment. Generalizing skills to the natural environment requires that the caregiver's behavior transfer from control of stimuli in the contrived setting to stimuli in the natural environment, and the skill continues to be performed with high levels of accuracy. The purpose of this study was to assess the extent to which caregivers generalized the use of social reinforcement, in the form of descriptive praise, from the contrived setting to the natural environment. When caregivers failed to respond to opportunities, a progressive prompt delay was used to bring caregivers' responding under the control of relevant client behavior; feedback was used to improve the accuracy with which caregivers implemented reinforcement. Five caregivers in a large residential facility participated in the study; single-opportunity probes were used to assess caregiver's identification of opportunities and accuracy in implementing reinforcement for two defined client behaviors, compliance and appropriate attention-getting behavior. Results of the study suggest that skills failed to generalize from the contrived setting to the natural environment. However, prompting was effective in training caregivers to identify opportunities to provide reinforcement, and feedback improved implementation of reinforcement.