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The Allied situation in the spring of 1942 was grim. The Germans had penetrated deep into Russia, the British Eighth Army in North Africa had been forced back into Egypt, and, in Western Europe, the Allied forces had been pushed across the English Channel to Britain.

At this point the Allied forces weren't strong enough to mount "Operation Overlord," the full-scale invasion of Western Europe. Instead, the Allies decided to mount a major raid on the French port of Dieppe. It was designed to test new equipment, and gain the experience and knowledge necessary for planning a great amphibious assault that would one day be necessary to defeat Germany. Also, after years of training in Britain, some Canadian politicians and generals were anxious for Canadian troops to experience battle.

To achieve these goals, plans were made for a large-scale raid to take place in July 1942, called "Operation Rutter." Canadians would provide the main assault force, and, by May 20, troops of the 2nd Canadian Infantry Division were on the Isle of Wight, in the English Channel, training intensively in amphibious operations. Poor weather in July, however, prevented them from launching Operation Rutter. Many involved in the planning wanted to abandon the raid. Despite the debate, the operation was revived and given the new code name "Jubilee." The port of Dieppe on the French coast remained the objective.

The Raid on Dieppe took place on the morning of August 19, 1942. The forces attacked at five different points on a front roughly 16 kilometres long. Four simultaneous flank attacks were to go in just before dawn, followed half an hour later by the main attack on the town of Dieppe itself. Canadians were the force for the frontal attack on Dieppe, and also went in at gaps in the cliffs at Pourville, four kilometres to the west, and at Puys to the east. British commandos were assigned to destroy the coastal batteries at Berneval on the eastern flank, and at Varengeville in the west.