A watan Nuwamba, 1942, Orebaugh ya kasance wakili a Ofishin Jakadancin Amurka a Nice, Vichy Faransa. A kan umarnin "Chargé d'Affaires" na Amurka Pinkney Tuck, da sauri ya kafa ofishin jakadancin a Monaco. Dalilin kafa ofishin jakadancin a Monaco ya fito fili bayan 'yan kwanaki tare da
Allied mamaye Faransa Arewacin Afirka da kuma sauri rufe Amurka diplomasiyya missions a Vichy Faransa. Amurka ta yi fatan samun tashar sauraro a Monaco mai zaman kanta wanda za a yi amfani da ofishin jakadancin. Koyaya, jim kaɗan bayan da Orenbaugh ya kafa ofishin jakadancin Monaco sojojin Italiya suka mamaye shi kuma shi da ƙananan ma'aikatansa sun shiga hannun Italiya. Daga nan sai aka tura shi zuwa Italiya inda za a yi musayarsa a kan fursunonin Allied. Amma bayan Armistice na Cassibile da kuma aikin Jamus na arewacin Italiya da kuma kwance makaman sojojin Italiyanci ba na Fascist ba ya sami kansa a cikin Jamhuriyar Social Republic na Italiya da ke cikin haɗarin zama fursunonin Jamus yayin da sojojin Jamus ke gabatowa wurin da aka tsare shi a Perugia. Ya zabi ya tsere tare da taimakon wani dangin Italiyanci na gida wanda ya ɓoye shi a gidansu. Yayin da aka kama shi a Italiya ya yanke shawarar taimaka wa kungiyar 'yan adawa ta Italiya kuma ya zama jagora a cikin kungiyar' yan adawa da ake kira San Faustino Partisan band. Ya shiga cikin ayyuka da yawa a cikin tsaunukan tsakiyar Italiya kuma wani lokacin yana jagorantar hare-hare masu ban tsoro a kan kayan aikin Jamusawa da na Fascist na Italiya da kuma kayan ajiya. Shi da wani dan Italiyanci na Italiya sun tsere zuwa wani ɓoye tare da sauran ma'aikatan Allied kuma daga bisani ya tashi a cikin jirgin ruwa tare da wasu 'yan Birtaniya da Amirkawa zuwa Allied Lines a ranar 10 ga Mayu, 1944. Ga Allies ya sami damar ba da cikakken bayani game da juriya na Italiya da sojojin Jamus kuma ya taimaka wajen sauƙaƙe hanyoyin samar da kayayyaki ga ƙungiyoyin juriya a bayan layin Axis. Bayan ya koma Amurka na ɗan gajeren lokaci, ya koma Italiya kafin ƙarshen yaƙin kuma ya yi aiki a matsayin wakili a Florence.