At 16:00 on the 10th February, General Dobbie, the Governor of Malta, arrived for a final inspection, and an hour later the men were issued boiled eggs and tea. Major Pritchard then gathered them around provoked a chorus of cheers when he finally revealed that they were about to parachute into Italy and demolish an important aqueduct, though even at this late stage only the officers were made aware of the escape plan to the submarine. In very high spirits, "X" Troop boarded the Whitleys.

The aircraft were divided into three groups. Those carrying the Covering Party were to take-off first at 17:40 with the sticks of Major Pritchard, and Lieutenants Jowett and Deane-Drummond, followed ten minutes later by the two diversion aircraft carrying a heavy bomb load, and then the Demolition Party at 18:00 with the sticks of Captain Daly, Lieutenant Paterson, and Sergeant Durie.

All proceeded according to plan except for Captain Daly's aircraft, which on the flight to Malta had already suffered more than its fair share of misfortune when it was chased by a Bf-109 and later drifted off course. Corporal Chapman reported that he was feeling ill shortly before take-off, and with no time for a medical examination or even to arrange for one of the reserve men to take his place, all they could do was to remove him from the aircraft and proceed to Italy a man short. Even so they were not airborne until 18:17, some 15 minutes behind the rest. It has never been definitively established what was troubling Chapman, it may have been the local stomach complaint known as "Malta Dog", but it seems that he was genuinely in some discomfort as no disciplinary action was taken against him on his return to the UK, and he continued to serve with the 11th SAS for several months before, as was not unusual at the time, requesting to be returned to his former unit.

The three sub-flights proceeded to the south of Malta and formed-up over the sea, and were only permitted to begin their northwards journey once it had become dark. Captain Daly's aircraft never caught up, however, and had to make its way to Italy alone. They proceeded North-West and crossed the Sicilian coast near Agrigento, then headed North to Palermo, where they encountered some flak. The aircraft then turned directly towards the River Sele, and on reaching the Italian coast quickly identified the river and followed its course inland towards the aqueduct. Daly's unhappy aircraft was not so fortunate, as they arrived to find the coastline partially obscured by mist and began to follow a different river, but once the mistake was realised they returned to the coast and proceeded up the River Sele, but some 90 minutes behind the rest.

The main formation passed over the aqueduct as planned and at 21.25 began to circle over the prominent feature of Monte Vulture, waiting for the order to begin the run in to the drop zone. Despite a little mist, the conditions were excellent and the aircrews had no difficulty in identifying the aqueduct and the surrounding landmarks. To avoid congestion over the drop zone the aircraft were to proceed one at a time in five minute intervals, with the first due to move off at 21.35. Some of the aircrews reported that they would not be ready in time, and so this was put back to 22:00, which gave Pritchard the opportunity to confer with the pilots of each aircraft and confirm that they had identified the objective. The message ordering the delay did not reach Lieutenant Deane-Drummond's aircraft, however, and it proceeded to the aqueduct at the earlier time and dropped its men at 21:42, with the rest following half an hour later. Captain Daly's aircraft suffered yet more bad luck as the drop zone was misidentified, and at 23:00 he and his men dropped six miles away in the neighbouring valley, too far to be of any use. "X" Troop had therefore been robbed of the man who was to organise the demolitions, along with four sappers and six containers of explosive; though due to a problem with the release mechanism these had not been dropped.

With the drop complete, the seven aircraft equipped with bombs proceeded to carry out their raids. Pilot Officer Wotherspoon's Whitley, one of the two diversion aircraft with a heavy bomb load, suffered a port engine failure, and at such a low altitude he was fortunate not to lose control. Unable to carry out their mission, the bombs were jettisoned and they attempted to limp back to Malta on one engine, but this lost some of its coolant and began to overheat. As they could go no further, Wotherspoon was forced to ditch near the coast in the hope of being rescued, but all were taken prisoner.

Sergeant Ennis in the other diversion aircraft proceeded to Foggia alone and caused considerable mayhem; scoring a direct hit on the aerodrome, two on the railway station, with a third hitting a line junction; in the course of all this a petrol train caught fire, two others were possibly damaged, and another was machine-gunned as it attempted to flee. The remaining aircraft carried a lighter bomb load, several of which hit the railway yard at Rochetta Scalo, with single bombs being dropped on the village of Montiverdi, a railway junction near the mouth of the River Sele, and at a place near Sciaro in Sicily.