Aim: To evaluate the reliability of linear and angular measurements taken using different software programs in orthodontics. Materials and Methods: A sample of four software programs from different manufacturers, namely MicroDicom viewer, Photoshop® CS3, AutoCAD®, and Image-Pro®, were used for measuring the geometric features of four types of miniscrews from different manufacturers. Each miniscrew type presented a group: Group I, Tomas® (Dentaurum, Ispringen, Germany); Group II, HUBIT® (HUBIT, Gyeonggi-do, Korea); Group III, AbsoAnchor® (Dentos, Daegu, Korea); and Group IV, Creative (Creative, Zhejiang, China). Measurements of apical face angle, thread angle, lead angle, flank, pitch depth, and width were taken on 45 × magnification scanning electron microscope images of the shafts of the miniscrews. One assessor measured the seven geometric features for the four types of miniscrews using the four software programs twice in two sessions separated by a three week interval. Results: Pairwise comparisons, for each of the four miniscrew groups, showed that the only common result observed was the significant difference (p < 0.001) between measurements of flank taken by the four software programs. When measurements of the four types of miniscrews were pooled into one group, a high degree of intra-rater reliability (ICC range from 0.9 to 1.0) for all the seven geometric features was found with all the four software programs. The paired t-test showed insignificant difference (at p ≤ 0.05) between the first and second measurements, except for a few measurements including pitch width measured by Image-Pro® (p = 0.012), MicroDicom (p = 0.023), and Photoshop® (p = 0.001). Conclusions: Results did not give absolute superiority to one software program over the others and suggested an assessor effect. Assessor estimates could have been affected, among other factors, by the design of the miniscrews and the technical features of the software programs.