Ordered to evacuate Alexandria in the face of the German advance after the Battle of Gazala in May 1942, Medway sailed for Lebanon at the end of June, escorted by a light cruiser and seven destroyers.

Built with bilge keels only 12 inches (305 mm) deep, Medway once rolled 42° each way with a period of nine seconds, losing her main topmast.

[3] The ship was powered by MAN diesel engines rated at 8,000 brake horsepower (6,000 kW), driving two shafts, and had a top speed of about 15 knots (28 km/h; 17 mph).

The ship had five 560-kilowatt (750 hp) diesel generators for electrical power and special provisions to recharge submarine batteries.

A report in The Singapore Free Press and Mercantile Advertiser on 27 July 1929 notes that HMS Medway was undergoing trials.

Colin Cantlie HMS Medway sailed to Hong Kong with six O-Class submarines of the Odin group.

[9] Two years later, Vice-Admiral Henry Harwood, Commander-in-Chief, Mediterranean Fleet, ordered all non-essential ships to leave Alexandria in June 1942 as he was preparing to demolish the port facilities there to prevent their capture by the advancing Panzer Army Africa.

[4] Accompanied by the Greek ship SS Corinthia, Medway was escorted by the light cruiser Dido and the destroyers Sikh, Zulu, Hero, Exmoor, Aldenham, Croome, and Tetcott.