On February 16, 1942, German U-boats began their attack on the Allies in Caribbean waters. It was a strategic and calculated attack. In Aruba and Curacao millions of barrels of oil derivatives and gasoline were produced weekly and much of American shipping to and from South America traveled through Trinidad. The initial offensive continued through July of 1942.

Rear Admiral John H. Hoover was Commander of the Caribbean Sea Frontier. He had less to work with than the other sea frontier commanders. In Aruba he had only one Dutch motor whaleboat, three coast defense guns and a few Army Air Force medium bombers to defend the valuable oil industry. On Feb 16, 1942 a German U-boat shelled a shore refinery. That same day six ships were sunk.

The United States had acquired the right to build military bases in Trinidad in the destroyer-naval base deal of September 1940. Construction began in May of 1941, but by the time of the Pearl Harbor attack, Trinidad was still primarily undefended. Trinidad had two converted yachts, two yard-patrol craft, four Catalinas and one utility transport with which to defend herself. The first U-boat attack off Trinidad occurred during the night between February 18 and 19.

Due to the United States lack of preparedness for war, the German U-boat operators had become bold and brass. On February 18, in the Gulf of Paria, a U-boat surfaced and pulled out of the harbor with running lights on after torpedoing two ships.

During the Caribbean Offensive the Allies lost 114 ships to German U-boat attacks. Thirty-One ships were lost in February and March, 41 ships were lost in April and May, and 42 ships were lost in June and July.

Kudos must be given to Allied rescue operations in the area, rescuing hundreds of survivors from torpedoed ships. Many rescue yachts and planes would drop off survivors, refuel and be off again looking for more victims. Shore crews worked around the clock repairing rescue vehicles. Many men worked until they were forced to rest by their superior officers.