296 Squadron was formed out of the Glider Exercise Unit at Ringway on the 25th January 1942, consisting at that time of a mixture of Hector and Hart aircraft. Several days later the Squadron moved to Netheravon, where they trained with Hotspur gliders carrying troops of the 1st Airlanding Brigade. A conversion to Whitley aircraft began in June 1942, and during the following month the Squadron was divided into 296A and 296B Squadrons. The former reverted to 296 Squadron on the 12th August and was moved to Hurn, whilst 296B was renamed the Glider Pilot Exercise Unit. On the 10th November, the Squadron performed its first operational sortie with a leaflet dropping mission over France, similar flights were carried out until May 1943. During February of that year, 296 Squadron began to replace its ageing Whitley fleet in favour of Albemarles.

Sicily

In June 1943, the thirty-two Albemarles of 296 Squadron flew to Sid el Ma in North Africa. On the 9th July, twenty-five of these participated in the lift of the 1st Airlanding Brigade to its landing zones near Syracuse, in Sicily, to spearhead of the Allied invasion. Due to a combination of poor weather conditions and the inexperience of the tug pilots, seventy-three of the one hundred and forty-seven gliders involved landed in the sea, only twelve gliders were able to land within a respectable distance of their objectives, and only one of these arrived on its intended landing zone. Despite this disastrous beginning, the 1st Airlanding Brigade managed to achieve all of its objectives, but it had come at a terrible cost of six hundred and five casualties, of whom three hundred and twenty-six had drowned.

On the 13th July, 296 Squadron flew to Sicily once more to drop the 1st Parachute Brigade around Primosole Bridge. It was not an accurate drop as only about a sixth of the one thousand eight hundred and fifty-six strong Brigade landed where they were supposed to, however the majority of the remainder were not scattered so very far from the Bridge, and so the paratroopers were narrowly able to defend their ground until relieving British armoured units arrived approximately twenty-four hours later.

This concluded the Squadron's activities in Sicily, and following a number of duties over Italy several months later, they returned to their Hurn base, in Britain, in October 1943. Thereafter, 296 Squadron's chief concern was training exercises alongside the Airborne Forces, though in February and March 1944, their aircraft were ordered to fly Special Operations Executive (SOE) supply drops to French Resistance forces. With the invasion of Normandy approaching, the Squadron was moved to Brize Norton.

Normandy

296 Squadron were charged with a number of tasks on the first night of the Normandy landings. Three of their Albemarles were ordered to drop thirty pathfinders onto DZ-N, near Ranville, to mark the zone of the main invasion force, which would arrive thirty minutes later. One of the aircraft carried men of the 22nd Independent Parachute Company, the other two contained the advance parties of the 5th Parachute Brigade. The Independent Company aircraft got into difficulties over the drop zone when the first man in the stick fell on the jump doors and there was a delay of ten minutes before he was extracted and the men could jump. Eight parachutists were able to exit the aircraft, but a second run had to be made to drop the remaining two. The first of the 5th Parachute Brigade aircraft, piloted by Wing Commander McMonnies, was able to drop its ten men without incident, Brigadier Poett being the first man of his Brigade to land on French soil, however Squadron Leader Archer's aircraft had to make a second pass over the zone to drop all of his troops. To round off what had been an eventful drop, these two latter Albemarles narrowly avoided a collision after they had left the zone behind them.

Thirty minutes later the main force of the 5th Parachute Brigade arrived over DZ-N. 296 Squadron provided eight Albemarles to this lift, each carrying nine paratroopers. As the formation approached Ranville it was met by a considerable amount of light flak and a number of aircraft were damaged, but the pathfinders on the ground had done their job well and all the men aboard the Squadron's aircraft made their jump. Flight Lieutenant Scott's aircraft was the only one to encounter any great difficulty during the drop and had to make no fewer than four passes over the zone. Three men jumped on the first run, however the doors then collapsed and the remainder were prevented from jumping. By the time the pilot had made a second run the paratroopers were not yet ready to jump, but on the third pass five men managed to get out. A fourth and final pass was made for the remaining paratrooper who jumped with a paradog, who had until that moment been hiding in the gun turret.

To allow the engineers of the 5th Parachute Squadron enough time to clear mined anti-glider obstacles from the drop zone, the main glider element of the first night's operations did not arrive until 03:35. Eight of 296 Squadron's aircraft towed Horsa gliders on this relatively small lift. Light flak and low cloud was met over the French coast and the tow rope on one Horsa broke away, it is believed that it was able to land on a beach. The remainder reached LZ-N safely. The Squadron suffered a fatality during this lift when the rear gunner of one aircraft was mortally wounded by a bullet fired from the ground.

When they returned to Brize Norton, the crews slept throughout the morning but were awake by midday, in time to be briefed for the Second Lift. Shortly before 19:00 on the evening of the 6th June, twenty of 296 Squadron's Albemarles took to the air again, each towing a Horsa glider. One of the gliders crashed on take-off and two more were lost en route, but seventeen successfully reached their landing zone. Little enemy ground fire was encountered, but it was nevertheless accurate and the Squadron suffered losses. One Albemarle crashed in flames, though four of the five-man crew managed to bail out, and several more aircraft were damaged, one of which had to make a crash-landing at Greenham Common.

This lift marked the end of 296 Squadron's operations in support of the 6th Airborne Division, however on the 7th June they were involved in another airborne drop, Operation Cooney. The Squadron provided three of the nine 38 Group aircraft that were involved in this effort, their Albemarle's each carrying six soldiers of the 4th French Parachute Battalion, SASB. In all, fifty-eight paratroopers were dropped on no fewer than seventeen undefended drop zones, between Redon and St. Malo, with the intention of disrupting enemy communications between West Brittany and the remainder of France. All of the drop zones were very small and a considerable challenge to locate, however 296 Squadron's navigators and bomb-aimers were successful in finding both of their allotted zones.

Arnhem

Due to the limited range of Albemarle aircraft, 296 Squadron temporarily relocated themselves to Manston for the duration of Operation Market Garden. On the 17th September 1944, the Squadron towed twenty-five Horsa gliders to both of the landing zones at Arnhem, four to LZ-S, the remainder to LZ-Z, while a further three aircraft flew to Nijmegen with Waco gliders carrying elements of 1st British Airborne Corps HQ. On the following day, twenty-one Horsas were towed to LZ-X at Arnhem, however two of these did not arrive. On the 19th September, only one aircraft represented 296 Squadron on the Third Lift, bringing in one of the Horsas that had failed to arrive on the previous day. With the airlift complete, the Royal Air Force concentrated on resupply flights to the 1st Airborne Division at Arnhem, but as the Albemarle was unsuitable for such work, 296 Squadron took no further part in Market Garden, having suffered no losses in either men or aircraft.

The Rhine Crossing

296 Squadron were moved to Earls Colne in the final days of September and began the conversion to the much more powerful Halifax V aircraft. With these they flew several SOE resupply sorties to resistance forces in several countries.

On the 24th March 1945, 296 Squadron deployed thirty Halifaxes to help carry the 6th Airborne Division to their drop zones around the Hamminkeln area to facilitate a crossing of the Rhine. In amongst the gliders that the Squadron towed were 6th Airlanding Brigade Headquarters, 3rd Airlanding Anti-Tank Battery RA, 53rd Airlanding Light Regiment RA, and the 195 Airlanding Field Ambulance RAMC.

When the War in Europe came to an end, the Squadron provided aircraft to transport elements of the 1st Airborne Division to Norway and Denmark, so that they might oversee the surrender of German forces in those countries. Thereafter their chief concern became the transport of liberated Prisoners of War to Britain. In December 1945, the Squadron undertook mail flights to India. 296 Squadron was disbanded on the 23rd January 1946.

Commanders of 296 Squadron