The current study aimed to quantify the length progression of enamel microcracks (EMCs) after debonding metal and ceramic brackets, implementing OCT as a diagnostic tool. The secondary objectives included a three-dimensional assessment of EMC width and depth and the formation of new EMCs. OCT imaging was performed on 16 extracted human premolars before bonding and after debonding. Debonding was conducted with a universal Instron machine, with ARI values recorded. Additionally, 2D and 3D OCT images were employed to detect EMC formation and progression. Enface images quantified the length, width, and number of EMCs, and the length and width were analyzed using Image J (1.54f) and MATLAB (R2014b), respectively. Sagittal cross-sectional images were used for EMC depth analysis. A paired t-test showed significant differences in the length, width, and number of EMCs after debonding (p-value < 0.05), while the Wilcoxon non-parametric test indicated significant EMC depth changes (p-value < 0.05). No significant results were identified for the EMC number in ceramic brackets and EMC depth in metal brackets. Three-dimensional OCT imaging monitored existing EMCs at higher risk of progression and detected new EMCs following orthodontic bracket debonding. This study provides novel insights into EMC progression regarding the length, width, depth, and number after debonding.