July 16, 1941 - Enlisted in the Air Force in Cedar Rapids, Iowa while travelling there as part of an orchestra.

January 1942 - Graduated from ground mechanic training at Chanute Field in Rantoul, Illinois and was assigned to a reconnaissance squadron in Boise, Idaho. 

March 1942 - Assigned to Santa Ana, California as a flying cadet.  Classified as a pilot at Ryan Field, Arizona and then reclassified as a bombardier at Santa Ana.

August 1942 - Sent to Tuscon, Arizona; subsequently assigned to Kirtland Air Force Base in New Mexico.

December 12, 1942 - Earned diploma from the U.S. Army Air Forces for competing Aerial Bombardier training at the Army Air Forces Advances Flying School at Kirtland AFB, New Mexico.

May 24, 1943 - Arrived in European Theater of Operations as 2nd Lieutenant; joins the Whaletail II crew headed by Pilot Dexter Lishon, U.S. Army Air Corps 381st Bombardment Group, 534th Squadron.

August 24, 1943 - Commended for his performance in the bombing of important enemy installations in Paris/Villacoublay, France as bombardier in the leading aircraft of a formation of B-17 airplanes in the 1st Combat Bombardment Wing, European Theater of Operations, U.S. Army.

September 3, 1943 - Wounded during mission, hit in hand by shrapnel. The saying was that every flyer had a bullet with his name on it, but if it hit you and missed, you were safe for the tour. So pilots considered him a good luck charm; many pilots going on their final mission asked for Darrell as their bombardier.

September 12, 1943 - Darrell receives the Purple Heart for wounds received during September 3 mission.

September 1943 - Promoted to 1st Lieutenant.

October 8, 1943 - Darrell's original crew, the Whaletail II, is shot down - crew members survive but are German POWs. Darrell had been working for about three days straight without sleep and was given the option to fly with the crew or stay behind.  He was exhausted and decided to stay behind to get some sleep.

November 1943 - Received another Oak Leaf Cluster.

December 1943 - Promoted to Captain.

January 11, 1944 - Darrell earns the Distinguished Flying Cross for his service as bombardier in the leading aircraft of a formation of B-17s that destroyed assigned targets at Oschersleben, Germany.

February 1, 1944 - Darrell completes instruction to act as Navigator on flights involving the use of dead reckoning, pilotage and the use of radio aids.

Feburary 11, 1944 - Darrell completes his tour of duty

February 13, 1944 - Captain Debolt s awarded the Distinguished Flying Cross by John A. Samford, Brigadier General for his courage and skill in twenty five bombardment missions over enemy-occupied Continental Europe.  The commendation also notes that he had previously earned the Air Medal and Three Oak Leaf Clusters.

June 16, 1945 - Date of separation from the Army.