Henry enlisted into the Regiment in 1855 and shortly after enlistment he departed with the 95th to the Crimea to take part in the ongoing Crimean War of 1853-56. Henry and his Regiment were present at the infamous siege of Sevastopol, where ferocious fighting took place on both sides for many months.   

Following the war Henry returned to Ireland, but it was not long before he was sent away again, with the regiment, to take part in the Indian Rebellion of 1857-58.