On 9 September 1944 Field-Marshal Montgomery proposed a plan, called Operation Market Garden, to secure a bridgegehead across the Rhine. The operation called for a combined armor and airborne assault to seize and hold key bridges and roads deep behind German lines in Holland. The airborne phase of the operation consisted of capturing five bridges ahead of the armored force.
On 17 September 1944, as part of Operation Market Garden, the 505th made its fourth jump at Groesbeck, Holland, the largest airborne assault in history. During that fierce combat, two lightly armed platoons, at most 80 men, were surrounded by an entire German Infantry Battalion supported by tanks. The paratroopers fought back three savage German assaults and held their ground until relieved. The 505th received a second Presidential unit citation.
Its success, however, was short-lived because of the defeat of other Allied units at Arnhem. The gateway to Germany would not open in September 1944, and the 82nd was ordered back to France.