Penn enlisted as a sergeant in Co. H of the 42nd VA Infantry with his brother Greenville. In February and March of 1862, he was assigned to recruitment duty. He was wounded in the stomach at the Battle of Antietam on September 17, 1862. He was promoted to lieutenant in 1862 and to captain on June 3, 1863. He spent much of the rest of the war enrolling and training recruits as he had a surgeon's certificate of disability due to his wound. On December 11, 1863, he was appointed drill master and assigned to the Conscript Office until July 1864, when he was again assigned to recruiting duties in Southside Virginia.
After the war, Penn was a farm superintendent in Henry County (VA) in 1870, a farmer in Patrick County in 1880, and a grocery clerk in Martinsville, VA in 1900. Penn died on October 26, 1903 with his death attributed to a stomach cancer caused by his war injury.
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