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S/Sgt Henry Boylin graduated from 8th grade at the Lillesville Elementary School, North Carolina. The family moved to Jacksonville, Florida where he attended Jacksonville High School through his junior year. At the end of his junior year he quit high school to find work to help support the family. In the fall of 1940 he moved to Rochester, New York to temporarily live with his aunt and uncle and help with the care of his sister.

He joined the Regular Army in Rochester, New York on 14 December 1940. he received basic training in Camp Blanding, Florida.

He participated in campaigns in North Arfrica, Sicily, Normandy, Northern France and at the Siegfried Line.

S/Sgt Boylin was reported Missing in Action on 9 October 1944 and officially decleared dead one day and one year later.

He was awarded the Silver Star Medal twice, the second time posthumously. The citations stated:

"for gallantry in action in connection with combat operations against the enemy while serving with Company H, 18th Infantry Regiment, 1st Infantry Division in the European Theater of Operations. On 24 April 1943, Private First Class Boylin fearlessly advanced over hazardous terrain under heavy mortar and small arms fire and assisted in directing accurate artillery fire on enemy guns. His undaunted courage and unselfish action materially aided our forces in accomplishing their mission. Private First Class Boylin's actions are in keeping with the finest traditions of military service and reflect great credit upon himself, his unit, and the Army of the United States."

"for gallantry in action in connection with combat operations against the enemy while serving with Company H, 18th Infantry Regiment, 1st Infantry Division, in action in Normandy, France, 6 June 1944. On 6 June 1944, Staff Sergeant Boylin distinguished himself when the 18th Infantry Regiment came ashore as Easy Red in the early morning on Omaha Beach under the codename Operation OVERLORD. Staff Sergeant Boylin was among the Soldiers who started the lengthy Battle of Normandy, assaulting the heavily fortified, enemy-held beachhead after a difficult passage through the congestion off shore. These landings were a significant turning point in the war and resulted in the Liberation of Paris and the restoration of the French republic. Staff Sergeant Boylin's personal courage and gallant leadership were vital factors in the prompt accomplishment of his company's mission and reflects great credit upon himself, the 1st Infantry Division, and the Army of the United States."