[2] The siege had many consequences to the political, military and social environment in the contemporary Viceroyalty of New Spain which was ruled since 1810 by Francisco Xavier Venegas.

On 16 September 1810, Miguel Hidalgo y Costilla rose in rebellion, rallying the town of Dolores to fight for independence from the Spanish crown.

On 30 October, they routed a loyalist army at the Battle of Monte de las Cruces, and two days later they were at the gates of Mexico City where they were eventually pushed back to the area around Bajío.

Loyalist soldiers under the command of Félix María Calleja defeated Hidalgo's army for the first time at the Battle of Aculco, splitting the insurgents into different groups.

[3] Prior to his capture and subsequent execution, Hidalgo had confirmed José María Morelos as the commander of all rebel forces in the south of Mexico.

[4] The viceroy of New Spain, Francisco Xavier Venegas, in an effort to avert an assault on Mexico City, sent Calleja at the head of 5,000 soldiers to hold Morelos and his forces in the area around Cuautla.

Leonardo Bravo began an extensive trench fortification network around Cuautla and ordered that loopholes be made in the convent and many of the principal buildings.

On the morning of 10 February, the rebels learned of Calleja's arrival to Cuautla, causing Galeana to leave the fort and to fortify the town and the Convent of San Diego.

A few days later, 7,000 reinforcement loyalists troops arrived under the command of Ciriaco del Llano and José Gabriel de Armijo from Asturias, Guanajuato, Lovera, San Luis Potosí, Zamora and Tulancingo.

Calleja attacked the Loma de San Diego with about 500 soldiers with the goal of creating an observation post overlooking the city.

Morelos observed this from the loma of Cuautlixco, half a league away from Cuautla and made an attempt to stop the Spanish attack.

Morelos, realizing that an attack was imminent, gave the order that the rebels were not to fire upon the Spanish troops until they had reached the outskirts of the city.

[5] When the royalist army advanced to a position north of Calle Real, almost reaching the Plaza of San Diego, the rebels opened fire and the battle began.

A troop of royalist dragoons were at one point in a position to take the city center when a 12‑year-old boy named Narciso Mendoza fired a cannon into them, dispersing them.

After leaving behind a sizable portion of his munitions and taking a path around the Popocatépetl Volcano, Llano entered the Tierra Caliente on 28 February.

Morelos decided to delay the arrival of these reinforcements and sent a sizable force under José Antonio Galeana to occupy the Barranca de Tlayacac with orders to ambush Llano's army.

The battalions from Asturias and Lovera guarded the city from the barranco de "Agua Hedionda", named as such due to its abundance of sulfuric waters.

On 13 March, Calleja wrote the following letter to the viceroy: After many months of resistance, Matamoros was able to escape from Cuautla towards Toluca where López Rayón was waiting with a variety of supplies needed to sustain the rebel defense.

Being as the rebels were affected with a high level of disease (over half), Morelos and Galeana sent an emissary to the Spanish camp who returned with news that many of the Spaniards were sleeping and others were busy guarding the supplies.

Both sides inevitably claimed victory in this battle although shortly after their abandonment of the city, Morelos' army was completely routed and broken as a fighting force by the Spanish.

Calleja refused the offer and instead decided to return to Cuernavaca which he left in December of the same year to take command of Spanish forces in Mexico City.

The rebel movement was forced to flee to the south of the country where they attempted to take the city of Acapulco de Juárez, the main port connecting New Spain to the Philippines and other Spanish possessions in Asia.

Leonardo Bravo was captured at the hacienda of the Terrateniente, Gabriel de Yermo and was presented to Calleja who authorised his transfer to Mexico City for trial and execution.

Morelos, in an attempt to free his fellow rebel, offered a deal that would liberate all Spanish prisoners from the Siege of Cuautla (more than 200) in exchange for Bravo.