190 Squadron was formed as a night training unit at Rochford on the 24th October 1917. The Squadron was never deployed on active service during the Great War, but it continued to train pilots until its disbandment in April 1919.

The Squadron was reformed at Sullom Voe in the Shetland Islands on the 1st March 1943, from where, with Catalina aircraft, it flew anti-submarine sorties over the North Atlantic. 190 Squadron was technically disbanded on the 31st December of that same year, but it was reformed a week later, on the 5th January 1944, at Leicester East. Its first batch of Stirling aircraft arrived on the 20th January, and eventually it acquired an establishment of sixteen Stirling IV's with an additional four reserve aircraft. 190 Squadron, now a part of 38 Group, began a period of intensive training exercises to familiarise the crews with the dropping and supplying of Airborne troops. Actual training with paratroopers and gliders began in March and continued until the end of May.

Towards the end of March 1944, the Squadron received orders to move to RAF Fairford. To facilitate this, on the 22nd and 26th March, its Stirlings towed gliders, containing some of its equipment and personnel, to the new airfield. 190 Squadron's first operational sorties under Transport Command came in April, when several of their Stirlings, flying from the forward base of Tarrant Rushton, dropped arms to the French Resistance in co-operation with the Special Operations Executive (SOE).

Normandy

As part of the Normandy landings, 190 and 620 Squadrons, who shared Fairford, were detailed to take-off at 23:30 on the 5th June and deliver eight hundred and eighty-seven paratroopers of the 5th Parachute Brigade to DZ-N, near Ranville. 190 Squadron provided twenty-three aircraft for this lift, all of which dropped their troops, with the exception of one aircraft which could not locate the drop zone and so returned to base with its stick of paratroopers. Although they had not necessarily received any damage from enemy fire during this lift, twenty-seven Stirlings from both Squadrons were found to be in an unserviceable state upon their return, however by morning the ground crews had repaired all but two of these.

On the following evening, both Squadrons each provided eighteen aircraft to transport the main glider element of the 6th Airborne Division to their landing zones. Between them, the Horsas they towed carried two hundred and fifty-four men, thirty-three Jeeps, twenty-nine trailers, eleven motorcycles, and eight 75mm Pack Howitzers.

During the night of the 8th June, six Stirlings of 190 Squadron were involved in the resupply flight codenamed "Rob Roy II". All aircraft returned safely, having dropped a total of one hundred and forty-four supply containers and twenty-two panniers to the 6th Airborne Division.

The Squadron played no further part in support of the airborne landings and instead reverted to its former SOE resupply role. From the end of June until August, small numbers of between two and five Stirlings flew numerous sorties of this type, dropping parachutists and arms to the resistance forces. Some of these flights involved the transport and supply of SAS soldiers, operating deep behind enemy lines.

Arnhem

On Sunday 17th September 1944, 190 and 620 Squadrons played an important role in the first action of Operation Market Garden with each of them providing six Stirlings to carry the pathfinders of the 21st Independent Parachute Company, whose job it was to mark all three drop and landing zones for the First Lift, which began to arrive half an hour later. A further nineteen of 190 Squadron's aircraft were involved in this lift, each towing a Horsa glider, two of which were forced to cast-off prematurely. On the following day, twenty-one Stirlings were used in a similar capacity for the Second Lift, but again two of their gliders failed to reach the landing zone.

On Tuesday 19th September, the Squadron used sixteen of its Stirlings in the first major resupply effort, while a further two aircraft brought in the gliders that had cast-off on the previous day. Between them, 190 and 620 Squadron managed to drop seven hundred and forty-two supply containers and one hundred and twenty panniers. Two of the Squadron's aircraft were shot down by anti-aircraft fire. Aboard the first, all four aircrew and four RASC despatchers were killed, and on the second two aircrew and two despatchers perished, but five men survived.

Similar losses were sustained amongst the seventeen aircraft involved on Wednesday's resupply mission. Three aircraft were shot down, aboard one of which, eight aircrew and two despatchers died. By far the cruelest blow to the Squadron came on the following day. Only ten of its Stirlings were fit to participate in the drop, but due to a combination of intense flak and the presence of German fighter aircraft, seven were shot down and the lives of twenty-four aircrew and six despatchers were lost. Amongst the dead was the Squadron's Commanding Officer, Wing Commander G. E. Harrison DFC SS. The final resupply mission was carried out by seven Stirlings, without loss, on Saturday 23rd September.

190 Squadron flew ninety-eight sorties during Operation Market Garden, and had suffered the heaviest losses of any of the sixteen squadrons in 38 and 46 Groups. Twelve Stirlings had been lost, thirty-nine aircrew and twelve RASC despatchers were dead, and fifteen aircrew had been taken prisoner. A further twenty-five personnel who had been shot down over Arnhem, however, had been able to return to the Allied lines when the 1st Airborne Division withdrew.

The Rhine Crossing

190 Squadron replaced its numerous losses from the Arnhem operation, and on the 14th October they left Fairford for Great Dunmow.

On the 24th March 1945, they took part in the airlift of the 6th Airborne Division to the Hamminkeln area as part of Operation Varsity, the second attempt to establish a bridgehead over the River Rhine. Thirty aircraft were used, each towing a Horsa glider, six of which contained divisional units whilst the remainder carried men and equipment of the 12th Battalion The Devonshire Regiment. Although losses amongst the airborne troops were extraordinarily high, the deployment was a great success.

In April 1945, 190 Squadron were busily involved in flying stocks of petrol to units on the front line which were on the edge of their supply lines. In May, immediately after Germany surrendered, the Squadron transported elements of the 1st Airborne Division to Norway to oversee the disarmament. During the same month, 190 Squadron began to replace its Stirlings in favour of the more powerful Halifax aircraft. The post-war period was an extraordinarily busy time for Transport Command as supplies were now needed more than ever, and during the following months 190 Squadron were employed in a variety of general transport duties all over Europe.

On the 21st January 1946, the Squadron was renamed 295 Squadron.

Commanders of 190 Squadron