This study assessed the stress distribution (in eighty-one 3D models of the second lower premolar) in a stainless-steel bracket and enamel crown under 0.5 N of intrusion, extrusion, rotation, translation, and tipping during a horizontal periodontal breakdown of 0–8 mm. The FEA simulations (totaling 405) employed five failure criteria and assessed the adequacy and accuracy of Von Mises (VM), Tresca (T), Maximum Principal (S1), Minimum Principal (S3), and Hydrostatic Pressure. T and VM criteria showed no change in stress display areas during the periodontal breakdown, seeming to be more correct and adequate than the other three (with unusual stress displays). Both VM and T (found to be more adequate) generated maximum stress areas on the attachment side and the entire base of the bracket, confirming the non-homogenous stress distribution areas and the risks of bond failure. Rotation, translation, and tipping were the most stressful movements and showed slightly lower quantitative values for 8 mm bone loss when compared with the intact periodontium, while intrusion and extrusion showed the opposite behavior (slight increase). Periodontal breakdown did not influence the stress display in the bracket and its surrounding enamel area during the five orthodontic movements.