[1][2] After five years with a one-month leave of absence from January to February 1894, Bolles graduated 69th in a class of 73 cadets in June 1896 and was commissioned as an infantry officer.

[2] Before participating in World War I, Bolles was a distinguished graduate of the Army School of the Line at Fort Leavenworth, Kansas in May 1916.

[3] In 1923, Bolles was awarded the Distinguished Service Cross with the citation: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting the Distinguished Service Cross to Second Lieutenant (Infantry) Frank Crandall Bolles, United States Army, for extraordinary heroism while serving with 18th Infantry, in action during the attack on Jaro, Panay, Philippine Islands, 12 February 1899.

Even after he was seriously wounded in the leg he continued to encourage his men and could scarcely be prevailed upon to desist from attempting mounting his horse when so crippled as to be unable to do so.

After duty at the office of the Quartermaster General in Washington, D.C. until December 1912, he was transferred to the 3rd Infantry and given command of a company at Madison Barracks, New York from January 1913 to August 1915.

After attending the School of the Line, Bolles rejoined his regiment at Camp Eagle Pass, Texas as a company commander in May 1916.

[3] Detached from his regiment, Bolles served with the Maryland National Guard as a district range officer and inspector-instructor until April 1917.

[4] In 1919, he was awarded the Distinguished Service Cross with the citation: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting a Bronze Oak Leaf Cluster in lieu of a Second Award of the Distinguished Service Cross to Colonel (Infantry) Frank Crandall Bolles, United States Army, for extraordinary heroism in action while serving with 39th Infantry Regiment, 4th Division, A.E.F., near Septsarges, France, 26 September and near Bois-de-Fays, France, 28 September 1918.

On 26 September Colonel Bolles personally directed the assaulting battalion of his regiment when the line was temporarily held up by hostile fire, leading the attacking troops forward to their objective.

After reaching the objective, terrific hostile fire caused many casualties, and the line was beginning to waver when Colonel Bolles assisted in the reorganization of the line, and by his personal example of courage and fearlessness encouraged his men to hold in the face of the withering machine-gun and artillery fire until the flank division had advanced abreast.

On 28 September he rallied his men under the sweeping fire of machine guns, minenwerfer, and artillery, and although painfully wounded, personally assisted in the reorganization of the positions.

[5][6]After recovering from his wound, Bolles returned to command the 39th Infantry from November 1918 to August 1919, when he reverted to his permanent rank of major.

Colonel Bolles commanded, with keen tactical ability, the 39th Infantry throughout the various campaigns in which the Fourth Division participated until the early stages of the Meuse-Argonne offensive, when he was wounded.

[5]Bolles was also made a chevalier of the Legion of Honour and awarded the Croix de guerre with palm and gilt star by France.