On 17 September 1944, "A" Company 48th Highlanders of Canada was given the task of attacking and capturing a position on flat ground, 300 yards northeast of a road junction known as Henly.

Sergeant Montgomery commanded the 8th Platoon of "A" Company, which was the leading Platoon of the assault.

When his Platoon was about 30 yards from its objective and in flat open country, it came under intense enemy MG fire. Faust patronens and grenades were also fired at very close range. Sergeant Montgomery immediately engaged the enemy with grenades. He threw seventeen in all, definitely killing three German Paratroopers. At the same time, he directed his platoon on to its objective.

On reaching the Company objective, his Company Commander ordered him to send one section of his Platoon to a house about 50 yards to the front. Sergeant Montgomery, having already had two of his NCO's wounded, personally led this section across open ground in the face of withering MG fire. They occupied and cleared the house of enemy.

During the assault on this house, one of his men was shot through both legs. Still in the face of the enemy fire, Sergeant Montgomery returned, picked up the wounded man and carried him forward into the house. Here he bandaged the wounded man's legs. At the same time, Sergeant Montgomery controlled and directed the fire of the Section.

During this fire fight, one man in the section accounted for 6 German Paratroopers including one Officer. On returning to his Platoon, Sergeant Montgomery carried the wounded man back across the fire swept ground.

The outstanding courage. initiative, and skillful leadership displayed by Sergeant Montgomery was unquestionably responsible for his Platoon gaining its objective and subsequently being reinforced by the remainder of the Company.

Throughout the entire engagement, Sergeant Montgomery displayed a bravery under fire which was an inspiration and example to the men of his whole Company. The skillful leadership and determination of this NCO was largely responsible for the success of "A" Company's attack.