Activated on 1 April 1941 as the 5th Reconnaissance Squadron, its personnel and equipment being drawn from the inactivated 27th Reconnaissance Squadron at Borinquen Field, Puerto Rico. The squadron had actually been constituted as early as 22 November 1940 to augment the reconnaissance forces available to the Puerto Rican Department. The squadron consisted of three Douglas B-18As, and these constituted the sole strength of the unit at Borinquen Field until the unit was redesignated as the 395th Bombardment Squadron (Medium) on 22 April 1942.
The 5th was initially attached as an element of the 40th Bombardment Group. A "Good Will" flight was made in July 1941 to Peru, stopping en route Trinidad, Albrook Field and Guayaquil, Ecuador, which gave the unit considerable confidence in the extent of their "reach" as a recon outfit. Between 4 and 16 November, the unit provided transportation throughout the Caribbean for a group of unidentified movie stars, stopping at Antigua, St. Lucia, Trinidad, Georgetown, St. Thomas, San Juan and back to Miami. That same month, one of the B-18s represented the Air Corps at the opening ceremonies for the new Pan Am airfield at Port-au-Prince, Haiti.
After the Japanese Pearl Harbor Attack, the unit was detached from the 40th Bomb Group and assigned briefly to the Antilles Air Task Force to perform antisubmarine patrols along the Antillies chain south to Dutch Guiana.
On 25 April 1942 the squadron was re-designated as the 395th Bombardment Squadron, and on 17 June, was transferred as such from Borinquen Field, Puerto Rico, to Rio Hato Army Air Base, Panama. Concurrent with this reassignment, the unit was reassigned to the 6th Bombardment Group on 9 August 1942. The Squadron received an infusion of new personnel in December 1942, when, upon inactivation of the 6th Bombardment Group, many of the former members of that headquarters were transferred to the 395th along with new aircraft. As of 27 December 1942, the Squadron had two Northrop A-17's, three Douglas B-18's, two Consolidated B-24D's and three LB-30's, three Boeing B-17B's and two B-17E's.
On 27 April 1943, the Squadron was transferred to David Field, Panama and, exactly a month later, moved from there to Howard Field in the Canal Zone, preparatory to its departure from the Command on 15 June 1943 as part of the takeover by the United States Navy of antisubmarine patrols.
Assigned to Pratt Army Airfield, Kansas in August 1943, being re-manned with new personnel. Received prototype and early production-model B-29 Superfortress very heavy bombers. Trained under Second Air Force for an extended period due to Boeing technicians making modifications of B-29 aircraft. Deployed to the new XX Bomber Command as part of the 58th Bombardment Wing in the China-Burma-India Theater, flying to bases in India via South Atlantic Transport route; across central Africa, Arabia to Karachi. Additional modifications of B-29s were necessary in India to accommodate very high ground temperatures (115 degrees F).
From airfields in eastern India, engaged in very long range bombardment raids on Japan. The squadron participated in the first American Air Force attack on the Japanese Home Islands since the 1942 Doolittle raid on 15/16 June 1944, attacking the Imperial Iron and Steel Works at Yawata on Kyushu by using its forward staging base at Hsinching Airfield (A-1), China, for refueling. Performed a total of nine missions to Japan, also engaged in very long range attacks against enemy targets in Thailand, Manchuria, Borneo, Formosa, Burma, Malaya, Japanese-occupied China, Singapore, Saigon and Cam Rahn Bay, French Indochina. Also engaged in aerial mining of Japanese-occupied seaports in Thailand Malaya and French Indochina.
Inactivated in October 1944 as part of a XX Bomber Command reorganization.
Reactivated in 1959 to (1) conduct Operational Readiness Training (ORT) and support the Combat Training Launch Program of the Titan I and (2) as part of the development of the LGM-25C Titan II Intercontinental Ballistic Missile. It operated one training facility for the Titan I, launch complex 395A, and three training facilities for the Titan II, launch complexes 395-B, 395-C and 395-D. B, C and D were constructed between 1960–1962 and turned over to Strategic Air Command in 1964. Flight test, evaluations, technical order verification research and development were performed at Vandenberg AFB.
The squadron was inactivated at the end of 1969, its mission turned over to the 6596th Missile Test Group on 1 January 1970.Constituted 5th Reconnaissance Squadron (Medium) on 22 November 1940
Activated on 1 April 1941
Redesignated: 395th Bombardment Squadron (Medium)
on 22 April 1942
Redesignated: 395th Bombardment Squadron (Heavy)
on 7 May 1942
Redesignated: 395th Bombardment Squadron (Very Heavy)
on 20 November 1943
Disbanded on 20 October 1944.
Reconstituted and redesignated as 395th Strategic Missile Squadron, 1 January 1959
Reactivated on 1 February 1959
Inactivated on 31 December 1969
40th Bombardment Group, attached on 1 April 1941, and assigned on 25 February 1942
Associated with: 1st Photographic Group, 10 Jun 1941-22 Apr 1942 (training)
6th Bombardment Group, 9 August 1942
40th Bombardment Group, 12 May 1943 – 20 October 1944.
1st Strategic Aerospace Division, 1 Feb 1959-31 Dec 1969 (Initially was the 1st Missile Division; changed to the 1st StratAD (SAC) in 1962)
Borinquen Field, Puerto Rico, 1 April 1941
Rio Hato AAB, Panama, 17 June 1942 – 16 June 1943
Pratt AAF, Kansas, 1 August 1943 – 12 March 1944
Chakulia AB, India, c. 11 April-20 October 1944
Vandenberg AFB, California, 1 February 1959 – 31 December 1969
B-18 Bolo, 1941–1943
Northrop A-17, 1942–1943
B-24 Liberator, 1942–1943
LB-30 (B-24A) Liberator, 1942–1943
B-17 Flying Fortress, 1942–1944
B-26 Marauder, 1943
YB-29 Superfortress, 1943
B-29 Superfortress, 1943-1944.
Titan I per Extract from 1MD Regulation Number 23-5 dtd 25 June 1960
LGM-25C Titan II, 1959–1969
Operated three launch silos at Vandenberg AFB for operational testing and development: