This dissertation is a diplomatic transcription edition and an analysis of BL Cotton Caligula Aii with emphasis on the Middle English romances in the manuscript and how the entire manuscript was compiled to teach lessons in obedience. The first section of the manuscript contains Sir Eglamour and teaches lessons in social obedience. The second section features three romances by Thomas Chestre: Octavian Imperator, Sir Launfal, and Lybeaus Desconus and teaches courtly and chivalric obedience. Section three features Emaré and teaches lessons in obedience and free will. The final section contains Sege of Jerusalem. Chevalier Assigne, and Sir Isumbras and focuses on obedience and the direct hand of God. The romances in CCAii, which have often been dismissed as overly simplistic or convention, become complex and meaningful text when they are analyzed as part of the compilation for which they were chosen and arranged.