From 1922 to 1923, he served with the Seventh Regiment of the New York National Guard in New York City where he also worked in financial services. Next came a career as chief purser on cargo and passenger ships travelling to South America, Europe, and Asia. In the 1930s, German and British passengers expressed fears about the Nazis, and military officers told him that Germany was equipping for war. Buckles witnessed antisemitism and its effects firsthand while ashore in Germany, and he warned acquaintances in Germany that their country would be brought down by Adolf Hitler, whom he encountered at a German hotel. Employed at sea during the Great Depression, he forwarded an $800 Army bonus to his father who was struggling as a farmer in the Oklahoma Dust Bowl (Buckles provided these details many decades later). As of 1940, Buckles had been employed by the White Star, American President, and W.R. Grace shipping companies, and in that year shipping business took him to Manila in the Philippines. After the outbreak of the Pacific War and the invasion of the Philippines, he reportedly remained in Manila to help resupply U.S. troops. He was captured in January 1942 by Japanese forces, and spent the next three years and two months as a civilian internee in the Santo Tomas and Los Baños prison camps. As a prisoner, he battled starvation, receiving only a small meal of mush served in a tin cup—a utensil he kept for the rest of his life. With a weight below , Buckles developed beriberi, and led fellow captives in calisthenics to counter the effects of imprisonment. Their captors showed little mercy, but Buckles was allowed to grow a small garden, which he often used to help feed children who were imprisoned there. All of the captives were freed following a raid by Allied forces on February 23, 1945. Before the war he had become fluent in German, Spanish, Portuguese, and French, and by its end had learned some Japanese. After World War II, Buckles moved to San Francisco and married Audrey Mayo in 1946. Eight years later, the couple bought the Gap View Farm in West Virginia where they raised cattle. Ancestors named Buckles had settled near Gap View Farm centuries earlier. In 1955, their only child, Susannah, was born. By then, the world traveller had settled down to a life of farm activities, social events, and serving as an officer (eventually president) of the county historical society. Audrey Buckles died in 1999, and their daughter moved back to the farm to care for him.