The regular battalions found themselves fighting in new roles: During the "Chindits" campaign in Burma, the 1st Battalion was part of the 77th Indian Infantry Brigade and were selected for conversion to the Chindits role and fought in Operation Thursday, the second Chindit expedition.During the expedition George Albert Cairns of the regiment was posthumously awarded the Victoria Cross. The battalion took part in jungle fighting against the Japanese forces. After serving as Chindits, they were transferred to the Parachute Regiment, becoming parachute infantry, and converted to the 16th Parachute Battalion. The battalion joined 50th Indian Parachute Brigade, part of the 44th Indian Airborne Division.
The 2nd Battalion, South Staffordshire Regiment was initially serving in the 31st Independent Infantry Brigade until 1941 when it was converted to a Glider infantry role, serving as part of the 1st Airlanding Brigade in the 1st Airborne Division. As such, they landed in Sicily in 1943 where they, along with the rest of the brigade, which was temporarily down to two battalions, suffered heavy casualties during the disastrous Operation Ladbroke. Because of heavy casualties during Ladbroke the brigade did not participate in the invasion of Italy and were withdrawn to England to prepare for the invasion of France. They took part in Operation Market Garden, and played a significant part in the Battle of Arnhem in September 1944