Parent’s ability to implement a skill like time out is considered to have generality when it lasts over time, it appears in environments in which it was not initially trained, and it is seen in use for child behaviors it was not initially trained for. A recent study suggested that parents have difficulty implementing time out in the home when they are supposed to (Jensen et al., 2016). The present study aimed to determine if there were difficulties in stimulus or setting generalization. Six parent participants completed pre and post training in-home naturalistic video observations, as well as a generalization probe role-play test following training. Results showed that parent’s accuracy and parent’s ability to implement when they should were two different skills. Parents scored high for accuracy of steps correct in both the post training in-home observations and the generalization probe role-plays. However, parent’s correct attempts out of the possible opportunities were only moderate in the post training generalization probes and poor in both the pre and post training in-home observations. How to implement time out was the only skill directly taught to parents and not when to implement time out. The authors suggest that knowing when to implement time out may be a generalization deficit and a recognition of opportunities in the home deficit. This version of time out training may benefit from additional training to foster generalization. Future research may benefit from systematically analyzing whether parents can recognize opportunities for time out in the home through other parent in-home videos and if they can, more emphasis on generalization of a skill to the parent’s home would be necessary in training.