War, Sherwood-Kelly served as a lieutenant with the Imperial Light Horse regiment that was used to hunt down the Boer kommandos on the veld. He joined the Somaliland Burgher Corps fighting Diiriye Guure of the Darawiish. During his time in Somaliland, Sherwood-Kelly's insubordination led him being demoted first to the rank of sergeant and then private. Upon his return to South Africa, Sherwood-Kelly went into business as the recruiter of black labour for the gold mines of the Witwatersrand and the diamond mines of the Kimberly range. In 1906 he took part in the suppression of the Bambatha Rebellion. After he was finished his service in Zululand, he married an Australian woman, Nellie, whose parents came to South Africa during the Witwatersrand Gold Rush. Prior to the outbreak of the First World War he was housemaster at Langley School, Loddon, Norfolk (England) and a member of the Territorial Force in the United Kingdom. First World War Gallipoli campaign In November 1914, Sherwood-Kelly was gazetted a major with the 10th Norfolk regiment. He repeatedly requested a transfer and was sent to the King's Own Scottish Borders in July 1915. At the Battle of Gallipoli, he commanded a regular army Scottish battalion and was awarded a DSO. He arrived on the Gallipoli peninsula in July 1915 at a time when the battle was already stalemated with the Allies unable to storm the heights of Gallipoli while the Ottomans were unable to push the Allies back into the sea. Sherwood-Kelly's nickname was "Bomb Kelly" owing to his enthusiasm for tossing Mills bombs into the Ottoman lines during the trench raids. The official history of the King's Own Scottish Borders marveled that Sherwood-Kelly "had a quite remarkable disregard for danger". On 15 October 1915, the battalion's commanding officer, Lieutenant Colonel G.B. Stoney was killed by an Ottoman shell that levelled the battalion's HQ. Captain G.S. Stirling-Cookson served as the acting commanding officer until 28 October 1915 when Sherwood-Kelly took command. The British historian Peter E. Hodgkinson noted there was a lacuna in the war diary of the King's Own Scottish Borders regarding Sherwood-Kelly who was not mentioned once between October 1915-January 1916 despite being the battalion's commanding officer, which he suggested was due to his unpopularity with his fellow officers as "an outsider and empire ranker commanding a regular unit". Western Front In January 1916, he arrived in France to take up service briefly