An ba shi izini na biyu a ranar 13 ga Maris, 1902, kuma an ba shi aiki a Presidio na San Francisco. Ya yi hidima a Philippines kuma daga baya a Alaska, kuma ya shiga cikin
tafiya zuwa Mexico tare da 16th Infantry Regiment a 1916. A lokacin Yaƙin Duniya na I, ya yi aiki a kan babban ma'aikacin na 1st Division kuma a matsayin mataimakin shugaban ma'aikata na 3rd Army. Bayan yakin, Short ya zama memba na Ma'aikatar War General kuma ya yi aiki tare da sashen Gabas ta Tsakiya na Ƙungiyar Harkokin Kasuwanci har zuwa 1924. Daga nan sai ya halarci Kwalejin Yaƙin Soja kuma bayan kammala karatu ya yi aiki a matsayin malamin makarantar ma'aikata. Ya umurci 1st Infantry Division daga 1938 zuwa 1940 da kuma I Corps daga Janairu 1940 zuwa Janairu 1941. Janar George Marshall ya nada shi zuwa umurnin Hawaii a ranar 8 ga Fabrairu, 1941. Ya sami lambar yabo ta Musamman kuma an yi la'akari da cewa yana da nasara a wannan lokacin, musamman ma saboda ci gaban da ya samu a lokacin zaman lafiya.