Introduction: Child weight and height are the basis of manufacturer and best practice guidelines for child restraint system use. However, these guides do not address behavioral differences among children of similar age, weight, and height, which may result in child-induced restraint use errors. The objective of this study was to characterize child behaviors across age in relation to appropriate restraint system use during simulated drives. Methods: Fifty mother–child (4–8 years) dyads completed an installation into a driving simulator, followed by a simulated drive that was video-recorded and coded for child-induced errors. Time inappropriately restrained was measured as the total amount of the simulated drive spent in an improper or unsafe position for the restraint to be effective divided by the total drive time. Kruskal-Wallis tests were used to determine differences across age in the frequency of error events and overall time inappropriately restrained. Results: Children in harnessed seats had no observed errors during trips. Within children sitting in booster seats there were differences in time inappropriately restrained across age (p = 0.01), with 4 year-olds spending on average 67% (Median = 76%) of the drive inappropriately restrained, compared to the rest of the age categories spending less than 28% (Medians ranged from 3% to 23%). Conclusion: Some children may be physically compatible with booster seats, but not behaviorally mature enough to safely use them. More research is needed that examines how child behavior influences child passenger safety. Practical Applications: Not all children physically big enough are behaviorally ready to use belt positioning booster seats. Primary sources of information should provide caregivers with individualized guidance about when it is appropriate to transition children out of harnessed seats. Additionally, best practice guidelines should be updated to reflect what behaviors are needed from children to safely use specific types of child restraint systems.