The chapter focuses on years 1387–91, covering Manuel's exile in Lesbos and Lemnos, and his subsequent return to Constantinople. Two of Manuel's works, the Discourse to Kabasilas and the Panegyric to John V, are analysed at length with regards to Manuel's self-representation, as well as their literary features and political messages. Manuel's daily life in Lemnos and his friendship with Kydones is discussed through their letters. The civil war between John V, John VII and Manuel is a prominent focus of the chapter, with e=special focus on Manuel's role in the events and how the episode influenced Manuel's later reign.