The chapter covers the blockade of Constantinople, 1394–1402. Topics discussed include Late Byzantine Constantinople, the socio-economic conditions during the siege of 1394–1402 and Manuel's political acts, his negotiations with Venice and his role in the Crusade of Nikopolis receive special attention. In the domestic spehere, Manuel's role in the anti-Palamite purges of 1369 and his stance towards Palamism is discussed at length. A little known work by Manuel, the Discourse to Iagoup, is analysed in light of Manuel's aversion to criticism, his views on Palamism, Orthodox and Catholic theology and the relationship between philosophy and theology. Once more, his self-representation and the political messages in the work, are taken into account. His Dialogue on Marriage is also analysed, focusing on its literary features, the representation of Manuel and John VII, and its political messages. Through the Dialogue and other works, Manuel's views on marriage are discussed. Finally, the chapter investigates Manuel's diplomatic relations with the West and his decision to travel to Europe to seek help.