Extractions are a common place in orthodontics. The present article discusses a rare case, in which a left maxillary canine along with two lower incisors was extracted. Atypical extractions such as these need to be duly justified and thought over before being carried out. In the case mentioned, all these teeth in question were ectopically erupted. When attempts were made to retract the canine in its right position, it exhibited gingival recession which would only go on increasing further as the distance from the transposed position in between the left central and lateral incisor to the original position was considerably large. It was planned that the 1st premolar would be converted to canine on completion of the treatment. The lower incisors too would have shown severe periodontal damage had attempts to align them was made. Not only were these two teeth lingually erupted but they also were rotated along their long axis. Derotation along with labial movement would have caused breakage of the supracrestal and transseptal fibers resulting in periodontal breakdown leading to mobility of these teeth. An esthetically and functionally balanced outcome was achieved following these extractions. In the upper arch, although the midline remained compromised, it was not worsened. In the lower arch alignment was achieved with preservation of the intercanine width. Complicated cases such as these require a thorough scrutiny of all available options. Whatever the treatment plan may be, the ultimate goal of functional and esthetic balance should be achieved.