© 2019 CEO This case reports the unsuccessful first treatment and the subsequent retreatment of a 35-year old Asian female with a skeletal class II with bimaxillary protrusion, complicated by a deep bite and vertical maxillary excess. This case report highlights the multiple facets of a challenging treatment plan and discusses the ramifications of treatment when treatment does not go as planned. The initial treatment plan consisted of a surgical approach with a maxillary Le Fort I surgery to correct the malocclusion as per the patient's requests without mandibular surgery due to the inherent risk of paraesthesia. The second treatment plan consisted of a bimaxillary surgery with genioplasty. The surgical treatment utilized virtual surgical planning (VSP). The orthodontic treatment was concluded with a corrected overjet and overbite achieving optimum function and balancing the facial profile aesthetically. This case report highlights the need for clear communication of the treatment plan and also the unpredictability of certain treatment outcomes especially when the literature does not provide for definitive conclusions. In addition, it sheds light on the challenge of unpredictable response of soft tissue after surgical treatment and the importance of patient expectations of outcomes. It is hoped that the paper provides a platform for future discussions of difficult malocclusions.