Kammala jumla mai zuwa: Daga baya ya koma Milan inda ya yi aiki a matsayin Mataimakin Jakadan Amurka a Milan na shekaru da yawa. Yayin da yake Italiya, Ambassador Lloyd Carpenter Griscom ya aika da Cutting zuwa Messina bayan
Girgizar kasa ta 1908 don kafa ofishin jakadancin kuma inda ya kasance daya daga cikin 'yan kasashen waje na farko da suka isa. Yankan "ya taimaka sosai wajen sauƙaƙa wahalar da ake sha a wurin". A shekara ta 1909, an nada shi Sakataren Ofishin Jakadancin a Tangier, wani birni a arewa maso yammacin Maroko wanda shine babban birnin yankin Tanger-Tetouan-Al Hoceima. Koyaya, Harvard ta ba shi lacca a kan Gwamnatin mulkin mallaka ta Biritaniya da ta fara a ƙarshen 1910, kuma saboda haka, ya yi murabus a matsayin Sakatare don shirya koyarwarsa. Daga nan sai Cutting ya tafi Masar don nazarin Gwamnatin Burtaniya a can kafin shirin ci gaba zuwa wasu yankuna na Burtaniya.