Orthodontic therapy could lead to marginal bone resorption in cases where the teeth are moved outside the envelope of bone. The purpose of this case series was to test corticotomy with a guided bone regeneration (GBR) procedure to regenerate bone in the direction of movement outside the original bony housing. Ten adult patients (60 anterior teeth), all presenting with severe anterior crowding, were enrolled in the study. Orthodontic therapy in all investigated sites was associated with selective surgical corticotomies and a simultaneous GBR procedure. CBCT examinations were performed before starting orthodontic treatment (T0) and at the end of treatment (T1; mean: 7 months; range: 6 to 9 months). Pre- and postoperative CBCTs were superimposed with a DICOM viewer (3D Slicer) and studied with an image-processing software (ImageJ, National Institutes of Health) to measure the area of interest of the buccal plate. The average area was found to be 0.58 ± 0.22 mm2 at T0 and 1.76 ± 0.4 mm2 at T1, with a statistically significant difference (P < .05). The combination of corticotomy and a regenerative procedure seems to have the ability to augment the original osseous anatomy when the root is moved outside of the original bony envelope.