Among orthodontists and scientists, in the last years, upper molar distalization has been a debated topic in the orthodontic aligner field. However, despite that few clinical studies have been published, no insights on aligners’ biomechanics regarding this movement are available. The aim of this study was to assess, through finite element analysis, the force system resulting in the upper arch during second maxillary molar distalization with clear aligners and variable attachments settings. The average tooth distalization was found to be 0.029, with buccal flaring of the upper incisors in all attachment configurations. The mesial deformation of the aligner was registered to be 0.2 mm on average. Different pressure areas on the interface between aligners and upper molars were registered, with the mesial attachment surface to be directly involved when present. Periodontal ligament pressure was reported to range between 67 g/cm² and 132 g/cm². Configurations with rectangular attachments from second molar-to-canine and from first molar-to-canine present, in an in silico environment, almost equal efficiency in distalizing the upper second molar. However, attachments from the second molar to the canine are suggested to be adopted in clinical environments due to greater feasibility in everyday practice.