'Gypsy' was a US airborne assault by Colonel Orin D. Haugen’s 511th Parachute Infantry of Major General Joseph M. Swing’s 11th Airborne Division on Camalaniugan airfield, to the south of Aparri on the north coast of the island of Luzon in the Japanese-occupied Philippine islands group (23/26 June 1945).
A task force of the 511th Parachute Infantry was delivered by a force of 54 Douglas C-47 Skytrain and 13 Curtiss C-46 Commando transport aircraft, seven of them towing Waco CG-4A assault gliders and the others carrying paratroopers, with the object of cutting the line of retreat of General Tomoyuki Yamashita’s 'Shobo' Group remnant of Yamashita’s own 14th Army toward any possible evacuation from the north coast.
The airborne force fought desultory actions with the Japanese for several days before linking with the spearhead of the northward advance of Major General Robert S. Beightler’s 37th Division of Lieutenant General Walter C. Krueger’s 6th Army.
Before this time, the regiment had fought in the 'King II' campaign to retake the island of Leyte farther to the south in the Philippine islands group. Here its task had been to take and hold the passes through the mountains in the centre of the island, in the process engaging and reducing the Japanese forces in the area with the ultimate objective of supporting the US forces in the battle of Ormoc that was proceeding at the same time. The regiment undertook its task during harsh monsoon weather in the steep, heavily forested terrain, emerging shortly after Christmas 1944 onto the Ormoc plain.
After rest and resupply, the regiment was sent to the island of Mindoro where the 11th Airborne Division was preparing for its part in the Battle of Luzon. On 3 February 1945 the 511th Parachute Infantry on board 48 C-47 aircraft performed a combat jump on Tagaytay Ridge, on which, for lack of adequate number of aircraft, the regiment and its associated elements jumped in three echelons. Despite some drops in the wing locations, the regiment assembled successfully at its drop zone at the Manila Hotel Annex on Tagaytay Ridge and proceeded in battalions to the north in the direction of Manila, encountering occasional Japanese resistance in the towns of Imus and Las Piñas before engaging the Japanese at the Parañaque river just to the south of Manila.
During the Battle of Manila, the regiment fought through the Japanese Genko defence line on 5/12 February, penetrating as far into Manila as the Dewey-Libertad area, before turning to the east to attack and take Fort William McKinley. On 23 February the 1/511th Parachute Infantry took part in the Raid at Los Baños, freeing more than 2,000 Allied civilians from a Japanese internment camp to the south of Manila, with its Company B performing a parachute jump on the camp itself.
The regiment next cleared a transport corridor from Manila to Lipa and Batangas City, which was needed for its important port, and took the crossroads town of Santo Tomas. With the rest of the 11th Airborne Division it also engaged Japanese forces throughout the provinces of Laguna, Batangas and Tayabas. The 1 and 2/511th Parachute Infantry were in 6th Army reserve in Batangas and Bauan, and the 3/511th Parachute Infantry in combat. on 27/29 April the regiment engaged and eliminated the remaining Japanese forces entrenched in underground complexes in the Mt Malepunyo range to the east of Lipa.
After 'Gypsy', the regiment remained in the in the area of Lipa and Batangas as it trained for the planned 'Olympic' invasion of Japan.