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Lieutenant-Colonel Sir Henry Pynn (1780 – 25 April 1855) was a British Army officer who served through the Napoleonic Wars, distinguishing himself leading Portuguese forces in the Peninsular War.

Early career
Henry Pynn began his military service as a lieutenant in the South Devon Militia. In 1799 he was recommended by John Rolle, 1st Baron Rolle, to receive a commission in a regular British Army regiment. He was duly appointed as an ensign in the 82nd Regiment of Foot, and on 28 November the same year was promoted to again be a lieutenant. With the Napoleonic Wars now underway, Pynn became adjutant to the regiment on 7 September 1804 and was then promoted to captain on 30 May the following year.