Whakaotihia te rerenga e whai ake nei: I te pakarutanga o te Pakanga Paniora-Amerika, ka uru a Upton ki te Ope Taua o te United States. I mahi ia hei tangata takitahi i roto i te Kamupene H o te 2nd Oregon Volunteer Infantry Regiment ka uru ki te hopu i Guam me te
Ngā pakanga o Piripi. I noho tonu a Upton ki te Kaitiaki Motu o Oregon i muri o te pakanga. I te tau 1911, i mahi ia hei kaitiaki matua o te 3rd Regiment o Oregon Infantry.