At present, temporary anchorage devices (TADs) are continuously gaining importance because of their usability and their possibility to broaden clinical force applications; however, how difficult can their placement planning be? Aim: The aim is to evaluate the association between clinical experience, digital knowledge and the capability of virtual planning in palatal orthodontic miniscrew insertion in various types of clinicians, divided by different levels of experience. Methods: A total of 30 participants (10 dental students, 10 orthodontics students and 10 orthodontists) with different levels of clinical and digital experience were randomly recruited in this cross-sectional study. All participants performed a pre-test survey followed by two consecutive digital planning tests and, finally a post-test survey. The digital planning test was made using software BlueSkyBio-BlueSkyPlan, a surgical guide module. The differences in terms of planning execution time, miniscrew insertion and surgical guide realization were evaluated. The Kruskal–Wallis and Mann–Whitney U-tests were performed to determine the effects of independent variables and interactions between groups. Results: The relation between clinical experience and bicorticalism was statistically significant (p = 0.017); in the planning execution time, a significant difference was evident between the dental students and the orthodontics students (T1: p = 0.015 and T2: p = 0.019), who, having good digital knowledge, took an average of 4.58 min less in T1 (p = 0.025), while this difference was significantly reduced in T2 (p = 0.106). Conclusion: Clinical experience increased miniscrew placement accuracy and digital knowledge reduced execution planning time but both had a stronger impact in the first test than in the second.