The history of Pruna is muddled, but certain facts are known. Greek artifacts have been found from when the Phoenicians managed the area, in fact it is believed that Pruna was named by the Greeks. Roman tombs and and ceramics have been discovered and a great walk is through the olive groves to a Roman Aquaduct.
After the take-over by the Moors, The Castillo de Hierro formed part of the defence system of this part of the Kingdom. The rocky outcrop above Pruna provided the ideal location for a castle and barracks. It formed part of a line of castles each of which was in visual contact with the next. Olvera, Vallehermoso, Zahara, and La Cordillera de Ronda la Vieja.
In 1250 Fernando III retook Pruna as part of the Christians reconquest of all of Sevilla. The next 157 years saw many battles until 1407 saw the definitive conquest of Pruna by the forces of Ferdinand and Isabella.
There is a gory story attached to the actual taking of the Pruna castle, passed down through the generations: The Moors were firmly entrenched in the heavily guarded barracks at the top of a very steep climb. So the locals went to a 'hill of oaks' and there they tied unlit torches to the tails of the goats. The goats were then taken to the bottom of the hill and the torches were lit. The goats scrambled to escape the fire climbing ever higher, setting the grassland alight as they ran. The terrified Muslim soldiers flung themselves over the cliff of the castle to get away from the flames and the monsters. So many died that the water was said to run red with blood, and the stream has been known as Arroyo Sanguino (river of blood) ever since.
From 1407 Pruna was protected by the Order of Calatrava, a religious military organisation,until 1457, when Enrique IV gave the village to Don Rodrigo de Ribera who by managing to keep Pruna safe from the Moors was therefore allowed to keep the land so long as he did not sell it.
The actual siting of modern day Pruna is thought to be the site of the old watch tower, at the side of the road between Ronda and Osuna, (on the present day Calle Ronda). He sent the population from the 'old' village of Pruna, beside the castle to this spot, in order to be 'Within range of a rifle shot of the castle and fortress of the village of Pruna'. It is thought the move was made to escape the unhygienic, and epidemic ravaged confines of the castle, which was also excessively hot in the summer.
In the 16th century Pruna became registered as a town, and then, in the 18th century Pruna was swapped for Villamartin by the Duque de Osuna, who made Pruna into a municipality with Algamitas and El Jaral.
The 18th century saw both an increase in prosperity, and population. In the 1787 census it had reached 2156 (1160 women and 996 men). Agriculture was the main economic activity, producing in order of importance: beans, wheat, barley, vines and olives.