Rolland enlisted in the U.S. Navy in February of 1941. After basic training at Great Lakes, his unit - Company #29 was sent to Pearl Harbor for transfer to destroyers by COMDESPAC (which was located on the USS Dixie at that time). Rolland was then transferred to the Flag Allowance. After two months, the USS Dixie was sent to California for new equipment and then sent to the South Pacific so Rolland was transferred to the USS Whitney where he was stationed during the Japanese attack. On the morning of the attack he was on the deck of the USS Whitney waiting for the motor launch to take him to Ford Island for church services. "Because I was with Flag Allowance, we had no battle stations. Due to the strafing by the Jap planes, we were ordered to go below deck as some were killed on deck. We had five destroyers tied next to us and would have been a prize target." Rolland later learned that, luckily, the Japanese canceled the third wave which would have hit the auxiliary ships. The Japanese thought the first two waves were a great success and didn't return.
"The noise below was very loud. We could hear the explosions. There was the smell of smoke and lots of confusion. After the attack, our Command was assigned the task of resigning the survivors to other ships. We would also assign all seamen arriving from the west coast. Every night, we would travel from the receiving station to the Whitney. There was a blackout and sometimes, we would be shot at. Everyone was trigger-happy and would shoot at anything moving in the harbor."
After serving on the Whitney, Rolland also served on the USS Markab and at Magazine Island in Pearl Harbor. Then, he returned to the states because the U.S. Navy scheduled him to attend Purdue University, but due to the Battle of Midway, all transfers were held up. "I was then sent to the University of Dubuque in Iowa and then to Northwestern where I received my degree. The Navy then sent me to Harvard for Officers Training and received my commission for supply corps duties. Then I was sent to the Naval Air Station in Jacksonville, Florida and qualified for aviation supply. Then I was given the choice of serving in Saipan or the Bikini Atoll. My choice was the Naval Air Station at Saipan and remained there until I was released from active duty on July 17, 1946. I then joined the reserves and was promoted to Lt. jg remaining with the group for three years and became part of the mobilization team during the Cold War."