On 13 October 2004, Sgt Jennings, acting as a sniper team leader attached to 3rd Platoon, Company E, in the city of Ar Ramadi, Iraq displayed great courage and commitment to duty. At approximately 0800, Sgt Jennings' sniper team departed the Al Anbar Provincial Government Center on foot moving south on "Central" Street towards "Baseline" Road. When the patrol reached the intersection of "Baseline" and "Central" they were ambushed by RPG and small arms fire. Sgt Jennings was wounded by shrapnel in his left knee. Despite his wounds, he continued to expose himself to enemy fire by providing first aid to the mortally wounded patrol leader and his radio operator. Sgt Jennings and his spotter, due to their vicinity to the detonation, were the first on the scene. The patrol leader's neck wound and was bleeding uncontrollably. The two Marines did their best to stop the bleeding using a compress and a packet of quick clot, before a Corpsman arrived to assess the situation.
After providing first aid and calling for a casualty evacuation, Sgt Jennings realized the radio operator was having trouble communicating their position to headquarters. Sgt Jennings then took control of the radio and talked the casevac into their position, relaying what he knew of the patrol leader and the radio operator's wounds. He then told 2ndLt Lavoie, the senior member of the patrol, that he was moving to an overwatch position to get better view on the surrounding area. The enemy was firing east of "Baseline" and "Central" unbeknownst to his team who thought the enemy was moving into alleys east of "Central". Engaging the insurgents with his sniper rifle, Sgt Jennings killed two.
Despite the shrapnel embedded in his knee, Sgt Jennings moved on foot with 1st Squad, 3rd Platoon, and elements of Whiskey 2, bounding in front of them east on "Central". From an overwatch position, Sgt Jennings killed an insurgent emplacing an IED.
 During a lull in the fighting, Sgt Jennings removed the shrapnel from his knee with his knife. The heat from the hot metal had cauterized the wound slowing down the bleeding. Sgt Jennings made a conscious decision to forgo medical attention in order to provide precision fire and overwatch for the patrol all morning. At no time did he request that his wounds be looked at or that he be medevaced. He displayed tremendous commitment to duty, great courage, and outstanding professional expertise in the face of enemy fire throughout the day.
On 17 November 2004, Sgt Jennings was serving in support of Company G as a sniper team leader at the Al Anbar Provincial Government Center. The Government Center came under sniper and mortar fire from 0800 to 1300. During the attack, Sgt Jennings exposed himself several times to enemy fire while assisting Observation Posts Two and Three engage the enemy. At Post Two, because the M240G couldn't traverse far enough to engage the enemy, Sgt Jennings took a Squad Automatic Weapon (SAW) from a Marine, leaned over the barrier and shot half a drum of ammunition at the enemy position using the tracers to guide fire onto the insurgent sniper's position. He did this knowing full well that accurate sniper fire was being received including two hits into the water containers behind him.
After returning the SAW to the Marine, he was exposed to fire again, running to Post Three in order to help another Marine walk 203 rounds onto the enemy's position. The Marine was subsequently shot in the head and collapsed onto Sgt Jennings. Sgt Jennings called for a Corpsman and began first aid by elevating the injured Marine's head and applying a bandage. Sgt Jennings also assisted the Corpsman in evacuating the Marine from the roof, under heavy sniper fire. He returned to his position on the roof to support Company G upon the completion of the medical evacuation.
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For heroic achievement in connection with combat operations involving conflict with an opposing force while serving as Team Leader, Section E, Scout Sniper Platoon, Weapons Company, 2d Battalion, 5th Marine Regiment, 1st Marine Division, I Marine Expeditionary Force from October to November 2004, in support of Operation IRAQI FREEDOM II. Sergeant Jennings received a wound in the left knee when the patrol was ambushed by rocket-propelled grenade and small arms fire. Despite his wound, he continued to provide aid to the mortally wounded patrol leader and the radio operator.
After providing first aid and calling for a medical evacuation, he continued to engage and eliminated two enemy with precision fire from an overwatch position. Despite the shrapnel wound to his knee, he completed a foot movement to a distant intersection where the patrol was again ambushed by small arms fire. He provided fire in support of the patrol and fatally wounded another insurgent with his sniper rifle. During a lull in the fighting, he removed the shrapnel from his knee with his knife and ignored medical attention in order to support the patrol.
On 17 November, he fought between posts at the Al Anbar Provincial Government Center helping thwart an attack by the enemy, firing 200 rounds from a squad automatic weapon over the government center wall to cover a blind spot being exploited by insurgents. He displayed great courage and outstanding marksmanship in the face of the enemy. By his zealous initiative, courageous actions and exceptional dedication to duty, Sergeant Jennings reflected great credit upon himself and upheld the highest traditions of the Marine Corps and the United States Naval Service. The Combat Distinguishing Device is authorized.
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