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Roquebert's expedition to the Caribbean was an unsuccessful operation by a French naval squadron to transport supplies to Guadeloupe in December 1809 at the height of the Napoleonic Wars. Over the previous year, British Royal Navy squadrons had isolated and defeated the French Caribbean colonies one by one, until by the autumn Guadeloupe was the only colony remaining in French hands. Cut off from the rest of the world by British blockade squadrons that intercepted all ships coming to or from the island, Guadeloupe was in a desperate situation, facing economic collapse, food shortages and social upheaval, as well as the impending threat of British invasion. In an effort to reinforce and resupply the colony, the French government sent four vessels to the West Indies in November 1809 under Commodore François Roquebert. Two of the ships were 20-gun flûtes carrying supplies and troops. The two others were 40-gun frigates, ordered to protect the storeships on their journey from the British forces operating off both the French and Guadeloupe coasts.
The squadron almost reached the Caribbean without encountering any of patrolling British warships sent to watch for French reinforcements, but was spotted and intercepted by the frigate HMS Junon on 13 December. Junon's captain did not realise the size of the French squadron until it was too late and, despite fierce resistance, his ship was captured and he was mortally wounded. Destroying the badly damaged Junon and continuing with the mission, Roquebert successfully delivered the flûtes Loire and Seine to within sight of Guadeloupe and then left them, his frigates making their way back to France without ensuring the safe arrival of their convoy. On 15 December, the small British brig HMS Observateur, which had witnessed the defeat of Junon, brought news of the French arrival to the blockade squadron anchored off Basse-Terre. Summoning ships from the surrounding region, the British commander, Captain Volant Vashon Ballard amassed a significant squadron and forced the French flûtes to anchor in a protected bay at Anse à la Barque, on the southeastern coast of Guadeloupe.
Ineffectual efforts were made to capture the flûtes, but it was not until the arrival of the 74-gun HMS Sceptre under Captain Samuel James Ballard that an attack was made in earnest. As small ships engaged the batteries on shore, two frigates entered the bay and attacked the flûtes, causing both to surrender in an hour-long engagement. Both French ships were badly damaged and a fire started during the engagement was able to rapidly spread through them, destroying both ships in succession. Many of the French crew escaped ashore from the wrecks, while others were picked up by British ships. The blockade of Guadeloupe was successfully maintained, and the island was captured in a coordinated invasion a month later. Roquebert's remaining ships were intercepted on 16 January by a patrolling British frigate, but successfully escaped pursuit and eventually returned undamaged to France.