He later moved to Milan where he served as Deputy United States Consul at Milan for several years. While in Italy, Ambassador Lloyd Carpenter Griscom dispatched Cutting to Messina following the 1908 earthquake to establish a consulate and where he was one of the first foreigners to arrive. Cutting "did much to relieve the suffering there." In 1909, he was appointed the Secretary of Embassy at Tangier, a city in northwestern Morocco that is the capital of the Tanger-Tetouan-Al Hoceima region. However, Harvard offered him a lectureship on British Colonial Government beginning in the fall of 1910, and he, therefore, resigned as Secretary to prepare for his teaching. Cutting then traveled to Egypt to study the British Government there before planning on moving on to other British Colonies.