10 Insane Covert Operations from WWII

Imagine dropping behind enemy lines with little more than a knife, a pistol, and a plan that sounds like pure madness. That was the daily reality for commando units during the Second World War. Their job wasn’t just to fight or kill; it was to disrupt and demoralize—cutting supply lines, sabotaging factories, and freeing high-profile prisoners of war while their main armies advanced. The risks were immense, as failure often meant death or torture, but that didn’t stop them.

From the Norwegian raid that disrupted Nazi nuclear ambitions to daring rescue missions deep behind enemy lines, these are some of the most remarkable—and often improbable—covert operations of the Second World War.

Related: 10 Insane War Stories That Turned Out to Be Myths

10 Operation Biting

In early 1942, the war in Europe had reached a tense and uncertain phase. German forces held a significant advantage in radar technology, particularly with the Würzburg system, which improved the effectiveness of their air defenses. The British, having already seen the importance of radar during the Battle of Britain, were determined to obtain and study this technology.

The resulting mission, codenamed Operation Biting, involved 120 commandos from C Company of the 2nd Parachute Battalion. Their objective was to parachute into occupied France near Bruneval, seize components of a Würzburg radar installation, and escape by sea. The team was led by Major John Frost and included Flight Sergeant C.W.H. Cox—a former cinema projectionist—who was tasked with identifying and dismantling the equipment.

Despite scattered landings and resistance from German defenders, the commandos successfully secured critical radar components before destroying the installation. They then withdrew to the coast and evacuated by boat. The raid provided valuable intelligence and demonstrated that Allied forces could successfully strike and extract from heavily defended positions.^[1]

9 Operation Frankton

By late 1942, Allied planners were searching for ways to disrupt German shipping operating out of the heavily defended port of Bordeaux in occupied France. Conventional attacks were difficult due to the port’s inland location and strong defenses.

Major Herbert “Blondie” Hasler proposed an unconventional solution: inserting commandos by submarine and having them paddle into the harbor using collapsible canoes. Operation Frankton began on December 7, 1942, when Hasler and eleven Royal Marines departed aboard HMS Tuna with six canoes.

The mission quickly encountered difficulties. Rough seas destroyed one canoe, others were lost or captured, and only a small group of commandos managed to reach Bordeaux after paddling nearly 70 miles (113 km) over several days. They successfully attached limpet mines to multiple German vessels, damaging or sinking several ships before attempting to escape overland. Only two men ultimately survived to reach safety.

Despite heavy losses, the operation demonstrated the effectiveness of unconventional naval sabotage. It became one of the most famous commando raids of the war.^[2]

8 Operation Flipper

In late 1941, British forces in North Africa faced increasing pressure from Axis troops under General Erwin Rommel. As part of a broader offensive, British planners authorized a commando raid aimed at disrupting German command operations by targeting Rommel’s headquarters in Libya.

Operation Flipper called for a small team to move behind enemy lines and attack what they believed to be Rommel’s command post. Led by Lieutenant Colonel Geoffrey Keyes, the force encountered severe challenges almost immediately. Adverse weather reduced the size of the team, leaving fewer than twenty men to carry out the mission.

After a difficult approach through harsh terrain, the commandos reached the target location, only to discover that Rommel was not present. A firefight followed, resulting in the death of Keyes and most of the raiding party. Only a handful of men survived to be captured or escape.

Although the operation failed to achieve its primary objective, it illustrates the risks associated with high-value targeted raids during the war.^[3]

7 Operation Chariot

In 1942, the German battleship Tirpitz posed a serious threat to Allied shipping in the Atlantic. British planners identified a critical vulnerability: the Normandie Dock at Saint-Nazaire in France, the only facility on the Atlantic coast capable of repairing a ship of its size. If the dock were destroyed, the Germans would be less likely to deploy the Tirpitz into the Atlantic.

Operation Chariot was designed to eliminate that capability. An aging destroyer, HMS Campbeltown, was packed with delayed-action explosives, disguised to resemble a German vessel, and rammed into the dock gates. Commandos simultaneously launched attacks on surrounding infrastructure to maximize damage.

The explosives detonated hours later, destroying the dock gates and rendering the facility unusable for the remainder of the war. The raid came at a high cost, with many commandos killed or captured, but it successfully removed a key strategic asset from German control.^[4]

6 The Fort Eben-Emael Raid

At the outset of the war, Fort Eben-Emael in Belgium was considered one of the strongest defensive fortifications in Europe. Positioned to guard key bridges over the Albert Canal, it played a crucial role in the region’s defense strategy.

On May 10, 1940, German forces launched a highly innovative assault using gliders to land troops directly on top of the fort. Approximately 85 specially trained soldiers used shaped charges and flamethrowers to neutralize artillery positions within hours.

The defenders, unprepared for an aerial assault from above, were quickly overwhelmed. The fort surrendered the following day, removing a major obstacle to the German advance through Belgium. While the assault force suffered relatively light casualties, the fall of the fort had significant strategic consequences, helping to accelerate Germany’s rapid advance into Western Europe.^[5]

5 Operation Jaywick

In September 1943, a team of 14 Australian and British commandos set out on a daring mission to strike Japanese shipping in Singapore Harbor. Departing from Exmouth, Australia, they sailed a captured Japanese vessel disguised as a local fishing boat, blending into coastal traffic as they moved through enemy-controlled waters.

Led by Major Ivan Lyon, the group spent weeks navigating toward Singapore before launching the final phase of the operation. From a point about 7 miles (11 km) offshore, small teams paddled collapsible canoes into the harbor under cover of darkness. On the night of September 26, they attached limpet mines to several Japanese ships anchored in the port.

The explosives detonated hours later, sinking or severely damaging multiple vessels. All members of the raiding party successfully escaped and returned to Australia. However, Japanese authorities, believing the attack had been aided locally, carried out reprisals against civilians in Singapore, underscoring the broader human cost of such operations.^[6]

4 The Pointe du Hoc Raid

Pointe du Hoc was a heavily fortified German position overlooking the Normandy coastline between Utah and Omaha Beaches. Its 155 mm guns posed a serious threat to Allied landing forces during the D-Day invasion. Neutralizing the site was considered critical to the success of the operation.

Lieutenant Colonel James E. Rudder led a force of U.S. Army Rangers tasked with scaling the 100-foot (30 m) cliffs under enemy fire, destroying the artillery, and holding the position against counterattacks. The assault was delayed by navigational difficulties and rough seas, complicating the already hazardous climb.

Upon reaching the top, the Rangers discovered that the main guns had been relocated inland. They eventually located and destroyed five of the six guns using thermite grenades, then held their position against repeated German counterattacks until reinforcements arrived. The mission succeeded, though the unit suffered heavy casualties, with losses estimated at around 70 percent.^[7]

3 The Gran Sasso Raid

In 1943, following Italy’s collapse as an Axis power, former dictator Benito Mussolini was arrested and held at a remote mountain hotel at Gran Sasso. Adolf Hitler ordered a rescue mission to recover his ally before he could be handed over to the Allies.

The operation, known as Operation Eiche, was led by German forces under Otto Skorzeny. On September 12, 1943, glider-borne troops landed near the hotel in a high-risk maneuver. Despite difficult terrain and the potential for resistance, the Italian guards—under orders not to engage—offered minimal opposition.

Mussolini was located quickly and flown out in a small aircraft, completing the rescue with remarkable speed. Although the mission was a tactical success and a propaganda victory for Germany, it had little long-term impact on the outcome of the war.^[8]

2 Operation Gunnerside

On February 27, 1943, a group of Norwegian commandos carried out one of the most significant sabotage missions of the war. Their target was the Vemork hydroelectric plant near Rjukan, which the Germans were using to produce heavy water—an important component in certain nuclear research efforts.

The team, trained by the British Special Operations Executive, approached the facility under extreme winter conditions. They descended into a deep gorge, crossed a frozen river, and climbed steep terrain to reach the plant undetected. Once inside, they placed explosives on key equipment used in heavy water production.

The charges destroyed critical components of the facility, disrupting production and forcing the Germans to reassess their program. Although the plant was later repaired, the raid significantly delayed progress and remains one of the most effective acts of industrial sabotage during the war.^[9]

1 The Cabanatuan Raid

On January 30, 1945, U.S. Army Rangers, Alamo Scouts, and Filipino guerrillas carried out a daring rescue mission at a Japanese prisoner-of-war camp near Cabanatuan in the Philippines. The camp held more than 500 American prisoners, many of whom were survivors of the Bataan Death March and were in poor physical condition.

Led by Lieutenant Colonel Henry Mucci, the rescue force traveled approximately 30 miles (48 km) behind enemy lines to reach the camp. Filipino scouts gathered intelligence on the layout, while a P-61 Black Widow aircraft flew overhead to distract Japanese guards at the start of the assault.

The attack was swift and highly coordinated. Within a short period, the rescuers neutralized the guards and evacuated 489 prisoners of war along with several civilians. Only a small number of Allied casualties were reported. The operation is widely regarded as one of the most successful rescue missions of the war and demonstrated the effectiveness of coordinated special operations in hostile territory.^[10]