PurposeThis exploratory study elicited the procedural considerations and inter‐radicular site placement techniques of experts and investigated how the use of a simulator, with and without feedback, influenced novice learners’ procedural considerations, placement techniques, and confidence.MethodsThree orthodontic/oral maxillofacial surgery expert clinicians participated in a temporary anchorage device (TAD) insertion assessment accompanied by a think‐aloud protocol. Expert transcripts were coded according to a coding scheme to analyze clinicians’ (N = 18) procedural considerations and placement techniques. Residents were randomly allocated to control and intervention groups. Two placement sessions were conducted at two inter‐radicular sites with audio recordings. The intervention group received real‐time feedback on root contact from the simulator's sensor and postoperative radiographs for self‐assessed feedback. Residents’ confidence levels were compared before and after placements, and subjective feedback about the simulator was obtained.ResultsThis study utilized the think‐aloud protocol to capture experts’ procedural considerations and placement techniques during TAD insertion and revealed a disparity between residents’ and experts’ thought processes. Only four out of 15 expert themes were mentioned by more than 50% of the residents. The use of the TAD insertion simulator in combination with feedback broadened residents’ procedural considerations after one round of placement. Residents’ confidence increased significantly in both groups (p < 0.05), but there was no significant difference between them (p > 0.482).ConclusionWhen used in conjunction with feedback, simulator practice of TAD insertion broadened residents’ procedural considerations after one round of placement. It improved residents’ confidence level and was well received as a learning tool.