Hugh Milbourne Jackson was educated privately and at the University College School, London. He then studied at the Royal Military Academy at Woolwich, London, and was commissioned to the Royal Engineers in June 1877. After serving in Bengal (in eastern India) from 1881 to 1883 he participated in the survey of India from 1883 to 1894. Returning to England he worked at the Ordnance Survey from 1894 to 1899. In the latter year he was sent to South Africa to participate in the Anglo-Boer War of 1899-1902, serving as head of topography of the Field Intelligence Department. He was awarded two medals with six clasps and attained the rank of Lieutenant-Colonel. In addition to various reports on his work he published a paper on "The employment of survey sections in war" in The Royal Engineers Journal (1906).
Later in 1902 Jackson served as acting president of the Natal Boundary Commission. In March 1903, he was appointed Surveyor-General of the Transvaal Colony, succeeding acting Surveyor-General W.H. Gilfillan*. He started publication of the Transvaal degree sheets, on a scale of 1 [English] inch = 1000 Cape roods (1:148 752), the last of which appeared in 1909. These maps were partly based on the rough military maps he had compiled during the war. In March 1904 he attended a geodetic congress in Cape Town at which the further geodetic survey of South Africa was planned. The next year he issued a pamphlet, Memoranda for the use of the plane-table (Pretoria, 1905). He served also as a member of the first Legislative Council of the Transvaal Colony.
In 1905 Jackson returned to the Ordnance Survey in England for a further three years and then served as Surveyor-General of the Federated Malay States from 1908 to 1915. During World War I he commanded a battalion of Royal Engineers in France and was awarded three medals. He retired in 1919.