Educated at Neuenhein College, Heidelberg and the Royal Military College, Sandhurst, Jackson was commissioned into the Border Regiment on 20 February 1897. He saw action at the Relief of Ladysmith and the Battle of Spion Kop in January 1900 and at the Battle of the Tugela Heights in February 1900 in South Africa during the Second Boer War. He served initially as a staff officer and then as commander of the 87th Infantry Brigade from January 1918 during the First World War. He became commander of 7th Infantry Brigade at Salisbury Plain in November 1923 and General Officer Commanding the 49th (West Riding) Infantry Division in September 1931 before retiring in September 1935.