On the outbreak of war in September 1939, "Gipsy" was deployed with the 1st Destroyer Flotilla for patrols and contraband control in the Eastern Mediterranean, based at Alexandria. "Gipsy" and her entire flotilla were transferred to the Western Approaches Command at Plymouth in October. On 12 November she collided with her sister ship, , en route to Harwich, and her new assignment with the 22nd Destroyer Flotilla, but she was only slightly damaged. The ship rescued three German airmen outside Harwich harbour on 21 November and returned to port to turn them over the army.