Surgery first approach is evolving as a better accepted treatment modality in contemporary orthognathic treatment. It has gained popularity gradually over the traditional orthognathic surgery as it involves performing of orthognathic surgery with minimal or no presurgical orthodontic phase. A correct diagnosis is the fundamentals of a precise treatment outcome. The present chapter discusses in detail about the diagnosis and treatment planning in surgery first approach as they lay the foundation for the best clinical outcome. This chapter is intended to provide an insight into the orthodontic and surgical consideration in surgery first approach. It entails the conventional as well as advanced diagnostic tools and treatment strategies in surgery first approach. It also encompasses the strategic planning of cases based on the specific requirements and objectives which further helps in execution of appropriate treatment plan. This chapter would thus be an essential guide for trainees and practicing clinicians in maxillofacial surgery and orthodontics.