Background: Aligner workflows range from outsourcing the design and manufacturing process to in-office scanning, planning, and fabrication. This exploratory retrospective study aimed to evaluate whether discrepancies between planned and achieved anterior tooth movements with SureSmile aligners remain within predefined clinical thresholds. Methods: A total of 21 dental arches from 14 patients who underwent SureSmile aligner treatment with in-office fabricated aligners were retrospectively analyzed. Digital models of the planned setup were superimposed on models of the clinically achieved outcomes to assess the accuracy of anterior tooth movements by comparing planned and clinically achieved outcomes. Results: Rotational movements showed larger discrepancies than translational movements. Mean discrepancies for angulation and axial rotation were 3.42 ± 1.50° and 4.50 ± 2.12°, respectively, both exceeding the predefined clinical threshold of 2°. In contrast, translational discrepancies remained below the clinical threshold of 0.5 mm, with mean values of 0.17 ± 0.11 mm for mesiodistal, 0.27 ± 0.16 mm for labiolingual, and 0.38 ± 0.17 mm for vertical movements. Translational discrepancies were significantly lower than the predefined clinical threshold in patient-level analyses, whereas rotational discrepancies were not. Conclusions: In-office SureSmile aligner workflows showed acceptable accuracy for translational anterior tooth movements, whereas angular movements frequently exceeded predefined clinical thresholds.