In 1817-18 he served with the 5th Native Cavalry in the Third Anglo-Maratha War and against the Pindaris, during which he was promoted Brevet Captain and appointed brigade major to the Nagpur Subsidiary Force.
In 1819 Caulfeild was appointed 1st assistant to the British Resident at Indore, after which his career was in the East India Company's Political Service.
He was Political Agent in Haraoti (the territories of Bundi and Kotah in the Rajputana Agency)[4] 1822–32, then Superintendent to the Mysore Princes in 1836, before being appointed Resident at Lucknow in 1839.
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.
[6] Caufeild was married a second time to Anne Rachel, daughter of the late Major William Blake of the 13th Bengal Native Infantry.