During the Peninsular War, especially during the first weeks of June 1808, Napoleon's troops had great difficulty in maintaining fluid communications between Madrid and Andalusia, mainly due to the activity of guerrilleros in the Sierra Morena. The first attack around Despeñaperros took place on 5 June 1808, when two squadrons of French dragoons were attacked at the northern entrance to the pass and forced to retreat to the nearby town of Almuradiel. On 19 June General Vedel was ordered to head south from Toledo with a division of 6,000 men, 700 horses and 12 guns to force a passage over the Sierra Morena, hold the mountains from the guerrillas and link up with Dupont, pacifying Castile-La Mancha along the way. Vedel was joined during the march by small detachments under Generals Roize and Ligier-Belair. On 26 June 1808 Vedel's column defeated Lieutenant-Colonel Valdecaños' detachment of Spanish regulars and guerrillas with six guns blocking the mountain pass of Puerta del Rey and the following day met up with Dupont at La Carolina, reestablishing military communications with Madrid after a month of disruption. Finally, General Gobert's division set out from Madrid on 2 July to reinforce Dupont. However, only one brigade of his division ultimately reached Dupont, the rest being needed to hold the road north against the guerrillas.