1506 siege where Castile peacefully retained control of Gibraltar fortress.
The 1506 Siege of Gibraltar, also called the Tenth Siege of Gibraltar, was an unsuccessful military operation by Juan Alfonso Pérez de Guzmán, Duke of Medina Sidonia. He tried to expel troops holding Gibraltar for the recently united crowns of Castile and Aragon. The four‑month blockade ended without casualties.
The 1506 Siege of Gibraltar, known as the Tenth Siege of Gibraltar, was a military operation centred on the fortress of Gibraltar. It followed earlier royal grants by which Henry IV of Castile had donated Gibraltar to Enrique Pérez de Guzmán, Duke of Medina Sidonia, as a reward for his family’s efforts and expenses in taking the stronghold from the Moors and administering settlers and the garrison. Ferdinand II of Aragon and Isabella I of Castile later granted the duke the title of Marquis of Gibraltar. In 1501 a royal decree ordered Garcilaso de la Vega to take over Gibraltar on behalf of the crown, and he formally assumed authority there in early 1502. After Isabella’s death in 1504, political instability in Castile encouraged Juan Alfonso Pérez de Guzmán to try to reassert his claim to Gibraltar by force during the power vacuum of 1506. From Seville he instructed his son Enrique to do whatever was necessary to recover the fortress. The operation became a four‑month “siege” in which Medina’s forces attempted to blockade rather than storm the stronghold. There was little fighting and no losses except from disease, and the duke eventually withdrew, paying compensation for local damage. Among Gibraltar’s many sieges, this was uniquely bloodless.