According to the included factory letter, this pistol was shipped as part of a 543-piece delivery to the Property Officer of the Supply Division of the Office of Strategic Services, located in the Fowler Building in Rosslyn, Virginia, on 11 August, 1944. Only in operation for a few years during World War II, the OSS was America's premier "dirty tricks" organization, responsible for cultivating intelligence sources in Axis nations, training insurgent groups, sabotage, and other assorted mischief and mayhem. The Colt Pocket Hammerless was acquired in quantity for their agents, as it provided a solid compromise between concealability and striking power, while also using ammunition and parts readily available through the Army supply chain. Fixed sights, with the two-line address and patent dates and the Rampant Colt on the left side of the slide, two-line caliber marking on the reverse, "U.S. PROPERTY" marked frame and "74" and "VP" on the trigger guard. Fitted with a pair of checkered medallion grips and a full blue magazine. Included with the pistol is a shoulder holster, constructed from soft brown leather with a green herringbone canvas chest strap, no makers marks, and a kraft-style box with the nomenclature "HOLSTER, SHOULDER/CAL. 32&380 COLT/1095-141-9494" on the lid. While technically an alternate option for American general officers, this pattern of holster is primarily associated with the OSS. Also included are a pair of "cloak and dagger" patches, featuring "O/S/S" in gold on a black field next to an outline of a black cloaked figure on a red background with a golden dagger; proposed after WWII by a former OSS man as a shoulder insignia for former OSS men who were still in the Army, the design was rejected but kept on file with the Institute of Heraldry, finding new life in the 1990s as a commemorative item.

Excellent with 98% plus of the original blue finish showing some surface blemishes on right side of rear slide, some light scratches and handling marks. The grips are excellent, with some light dings. The holster is near mint with a few light handling marks, and the patches are also near mint. Mechanically excellent.