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Operation Market Garden, launched in September 1944, was an unsuccessful Allied offensive mainly, fought in the Netherlands. It was the largest airborne operation in history up to that time. The operation was a daring one and it was the brainchild of the British General Bernard Montgomery. His intended the airborne offensive to allow the allies to break into the German heartland and to end the war, quickly. However, this was not the case, the allied offensive was to prove to be a costly failure and may have even delayed their victory in Europe. This article will discuss the reasons for the failure of the operation and they will be Montgomery's over-optimistic planning, poor strategy, poor leadership, German resistance and the terrain.