Sir Alan Cunningham was educated at Cheltenham College and then the Royal Military Academy after he joined the Royal Artillery in 1906. He served with the Royal Horse Artillery during The Great War being awarded an MC in 1915 and DSO in 1918. After the war he served in the Straits Settlements for two years. He then returned to Britain. In 1937 he became the commander of the 1st Division of Royal Artillery and then the commander of the relatively new Anti-Aircraft division.
At the outbreak of the Second World War, he was sent to command the troops in East Africa. He led the campaign to take Somaliland and Addis Ababa from the Italians. He achieved this in a very short period of time and took over 50,000 prisoners for the loss of only 500 of his own men. This success meant that he was trusted with command of the 8th Army in North Africa. Unfortunately, he was outfought by Rommel and was dismissed by Auchinleck. He was transferred to the Staff College and Northern Ireland before returning to the Middle East as High Commissioner of Palestine from 1945 to 1948. He continued to have a role as the Colonel Commandant of the Royal Artillery until 1954. He died in 1983.