Rubuta ci gaba don wannan sakin layi - Daga baya ya koma Milan inda ya yi aiki a matsayin Mataimakin Kwamishinan Amurka a Milan na shekaru da yawa. Duk da yake a Italiya, Ambassador Lloyd Carpenter Griscom ya aika da Cutting zuwa Messina bayan girgizar kasa ta 1908
don kafa ofishin jakadancin da kuma inda ya kasance daya daga cikin na farko kasashen waje zuwa zo. 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.