The objective of this study was to investigate the effects on a student’s metacognition, reflection, and learning in a specifically designed educational simulation supported by unique technology. The simulation allows players’ actions to be recorded for the purpose of review to identify mistakes. The simulation also allows students to start at and redo actions while fixing previous mistakes instead of starting over at the beginning of a new scenario. When starting at the mistake or point of failure, as identified by a facilitator, during the redo of the initial saved scenario, students reflect on the actions performed during the initial scenario. Student thinking during a redo of a scenario, after the initial scenario reflection, may be called reflective redo when the simulation technology can support starting from the point of failure. This research investigated how metacognition, reflection, and learning were affected by reflective redo. Two key findings were identified when analyzing reflective redo in how students. learn the content and how they learn about their own use of metacognition and reflection. The first key finding relating to the influence of reflective redo on learning was that participants used reflection at levels that matched their need as a support mechanism. The second key finding was that the students’ abilities to place themselves in the problem space contributed to the amount of contextual information they needed to be successful— in this case, either starting from the beginning or from the point of failure.