That same year Cloudsley was commissioned into the West Kent Yeomanry. In 1909 Cloudsley was promoted Lieutenant by which time had largely dropped out of first-class cricket.
Shortly after the outbreak of the First World War he was promoted to Captain and went with the regiment overseas, firstly to Egypt then Gallipoli and Palestine.
Cloudsley was taken ill shortly after the first battle of Gaza and returned to England in July 1917 where he served the remainder of the war.
Cloudsley worked as a land agent prior to World War 1 and in 1911 married Algitha Parker. After World War I he played club cricket for the Mote until his death in Wrotham Heath in 1928, aged 49.