While researchers have suggested that overlearning increases the likelihood of skill retention, there is little consensus or evidence as to how much overlearning is required, and how such overlearning interacts with distributed practice schedules. Additionally, most research has measured skill retention based on relatively short re-testing intervals of 56 days or less; however, little is known about whether overlearning can mitigate skill degradation when the retention interval is 6 or 12 months in duration. This research examined the relationship between overlearning and retention by measuring the amount of overlearning attained in a pistol training program and measuring skill across retention intervals of 1, 6 or 12 months. The results indicate that both test and re-test performance was better over 18 sessions vs. 9 sessions, although, doubling the number of trials for the participants who trained over 18 sessions demonstrated no discernible improvement. However, the number of sessions was not the only variable that predicted performance. It was clear that overlearning resulted in better overall skill retention and that when skill retention is critical, focusing solely on the number of training sessions will achieve only partial success of those goals.