Pre-mission experiments determined that the squadron's bombers could carry a bomb load over this distance with fuel tanks installed in their radio compartments despite having to take off from a runway damaged by enemy action.

On 16 September 1958, a B-52D (serial number 55-65) assigned to the squadron crashed in the vicinity of St Paul, Minnesota, while transiting en route on a continental United States (CONUS) training mission.

[4] During the Vietnam War the squadron deployed personnel and aircraft to Andersen Air Force Base, Guam and U-Tapao Royal Thai Navy Airfield, Thailand, for Operation Arc Light missions from 1968 to 1975.

[6] November 2010 saw the squadron deploy six B-52H Stratofortresses to Andersen Air Force Base, Guam for the first time since the Vietnam War as part of U.S. Pacific Command's continuous bomber presence.

[7] On 5 June 2015, the 69th deployed three B-52H Stratofortress bombers to RAF Fairford for two weeks for exercises BALTOPS 15 and Saber Strike 15 taking place in Europe.

[8] Four B-52H Stratofortress bombers from the 69th Bomb Squadron were flown to Nellis Air Force Base to participate in exercise Red Flag 15-3, which took place 13–31 July 2015.

The aircraft was assigned to the 69th Expeditionary Bomb Squadron, which was deployed to Andersen as part of the United States' Indo-Pacific Command's continuous bomber presence.

[15] In July 2019, the 69th Bomb Squadron deployed to Anderson Air Force Base, Guam, in support of the continuous bomber presence mission directed by the United States Indo-Pacific Command.

On 13 August 2019, a B-52H assigned to the 69th Expeditionary Bomb Squadron temporarily based at Andersen assisted in the search for the Indonesian-flagged fishing vessel KM Aleluya.

Adrift for 10 days without food, water or electricity, the crew was safely rescued by the AMVER vessel Isl Star, approximately 172 miles northwest of Palau.

[18] On 19 April 2022, the 69th returned from a deployment to RAF Fairford, England, where they supported multiple NATO exercises amid the Russian invasion of Ukraine.