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James Caulfeild was the son of the Venerable John Caulfeild, Archdeacon of Kilmore, County Cavan. He joined the Bengal Army in 1798, arriving in India in 1799. Apart from a period of sick leave in England from 1807-1812, he served in the military until 1819 when he was appointed as 1st Assistant to the British Resident at Indore. He continued to serve in an administrative capapcity as Political Agent in Haraoti (the territories of Bundi and Kotah in the Rajputana Agency)1822–32, then Superintendent to the Mysore Princes in 1836, before being appointed Resident at Lucknow in 1839. Meanwhile, his military career progressed through seniority: regimental Captain 1818, Major 1823, Lieutenant-Colonel 1829, Brevet Colonel 1834.
Caulfeild left India on furlough in 1841, and never returned. Promoted to Major-General in 1841 and Lieutenant-General in 1851, he was a Director of the East India Company 1848–51, and stood for Parliament, unsuccessfully contesting the seat of Abingdon in 1845 and 1847 before finally winning it in July 1852. Caulfeild's career as a Member of Parliament was short, however, because he died at Copsewood, Pallaskenry, County Limerick, on 4 November 1852.