Aim: The objective of this research has been to apply a specific simulation to a patient to assess the biomechanical consequences of rotating an upper canine tooth through different attachment–aligner configurations and to predict the most efficient design using a three-dimensional finite element model of a full maxillary arch of a specific patient. Materials and methods: This was obtained by combining Cone-Beam Computed Tomography (CBCT) with the aim of reconstructing tooth roots and bone tissues, and Surface Structured-Light Scanning for creating digital tooth crown models from the patient’s impressions. This model was imported into the finite element solver (Ansys® 17). Three different attachment–aligner combinations were created through the exploitation of computer-aided design (CAD) procedures, i.e., without attachments, with a couple of attachments and with an attachment and a pressure point. For each simulation, the resulting force–moment (MF) system applied by the aligner to the target tooth, as well as the tooth displacement and rotation, was computed using a workstation based on Intel Xeon CPU E3-1245 v3@3.40 GHz and 16 GB RAM. Simulations reported that by adding the pressure point and the attachment to the standard aligner the amount of Moment z (Mz) delivered to the tooth increased almost two times. Results and conclusions: The maximum tooth displacement (0.85 mm) was obtained with the attachment and pressure point aligner, while the lowest (0.058 mm) was obtained with use of a couple of attachments. Both the attachment and the pressure point have the potential to enhance the appliance’s effectiveness. Particularly, the pressure point showed a higher influence on the load absolute value. The method applied in the present study should be used to retrieve the best design configuration for each patient and specific tooth movement.