Aurangzeb himself had seen the political situation of the Deccan with his own eyes by being on the Deccan front and serving as the Subedari of the Deccan. Aurangzeb was also not unfamiliar with the spurt in Shivaji's activities since his departure from the Deccan. Aurangzeb felt that Shivaji was a future crisis for the Mughal Empire. Therefore, when Aurangzeb sat on the throne of the Mughals, he appointed his maternal uncle Shaista Khan as the Subedar of the Deccan and instructed him to go to the Deccan and annihilate Shivaji. Alamgirnama, the official biography of Aurangzeb, states in relation to this order that- "Being powerful, Shivaji gave up all fear and consideration towards the state of Bijapuri. He started trampling and destroying the Konkan region. Taking advantage of the occasion, he attacked the palaces of the emperor. The emperor then ordered Amir-ul-Amra (Shaista Khan), the Subedar of the Deccan, to march with a mighty army, try to suppress the lowly, seize his territories and forts and free the region from all unrest. .
Shaista Khan was a fool. He had experience of fighting many wars. In the beginning of AD 1660, he left for Aurangabad with a huge army and reached Ahmednagar on 11 February 1660. On 25 February 1660 he left Ahmednagar for the Deccan. Shaista Khan was still on the way when he got the news of Afzal Khan's death. He asked his army to move fast. Even before reaching the Deccan, he also got news of the failures of Fazal Khan, Rustameja and Siddi Jauhar. By the time Shaista Khan reached the Deccan, the Panhala fort had left Shivaji's hands. Shaista Khan reached Poona on 9 May 1660. Marwar King Jaswant Singh was also instructed to reach the Deccan to fight against Shivaji. He also started moving towards Poona with his huge army. Shivaji was in trouble after seeing Shaista Khan and Jaswant Singh coming with such a large army.
Kartalab Ali Khan was defeated
Shaista Khan himself occupied Poona and settled in Shivaji's residence i.e. Lalmahal and sent an army under the command of his warlord Kartalab Ali Khan to capture the forts in the Konkan region of Shivaji. At the end of AD 1660, Kartalab Khan came down from the Ghats near Lonavala with a heavy army. Shivaji was familiar with every corner of Konkan, so he allowed Kartalab Ali Khan to enter the heavy forest. Shivaji planned to encircle him in a pass called Umber Khind, from where Kartalab's escape was very difficult. This pass is built in the uninhabited hill located near the waterless area of 20-22 km long, from which even two men cannot pass simultaneously. There are high hills on both sides of the pass. Shivaji hid his army in these hills. In February 1661, the Mughal army reached Khind Pass with its artillery and logistics. Shivaji's army closed the roads both ahead and behind him. The Mughal army was surrounded in a limited area. Now Shivaji's men started attacking the Mughals from the top of the hills with stones, sticks and bullets. The Mughal army was trapped like a rat in a cage. In no time he ran out of water. Hundreds of Mughal soldiers were killed in this siege. Kartalab Ali Khan's own life was in danger. He sent a request to Shivaji to stop the war. Shivaji collected a heavy fine from him and took away all his military material. Kartalab Ali Khan returned to Shaista Khan with his remaining soldiers.
Right over the small princely states of Konkan Pradesh
After defeating Kartalab Khan, Shivaji decided to annex the towns of Dabhol, Sangameshwar, Chiplun and Rajapur of Bijapur state located in Konkan region and small princely states like Pali and Shringarpur in his kingdom. He kept an army under the leadership of Netaji Palkar who kept the Mughals entangled and started conquering the rest of the Konkan region by taking an army himself. He captured Shringarpur on 19 April 1661. Shivaji spent the summer of AD 1661 in Vardhangarh in Konkan Pradesh.
Shaista Khan's Man-Mardan
Shivaji wanted to drag Shaista Khan into the mountains of Konkan, so he was involved in the conquest of the forts of Konkan, but Shaista Khan understood that to go after Shivaji was to invite death. So he stayed in Poona. He captured many important forts of Shivaji's Poona, Panhala, Chakan etc. In May 1661, Shaista Khan also captured the forts of Kalyan and Bhiwandi. In AD 1662, the plains of Shivaji's kingdom also went under the control of the Mughals, but still a large number of forts were under the control of Shivaji, which Shaista Khan was not able to snatch. Shivaji's forces defeated Shaista Khan on many fronts and pushed back, but Shivaji's soldiers were also being killed in this campaign. It is believed that Shaista Khan deliberately wanted to prolong the campaign so that he would not have to go to Kandahar campaign led by Aurangzeb. Therefore, he continued to show Aurangzeb that the campaign against Shivaji was going on continuously. In January 1662, Shaista Khan set fire to 80 villages of Shivaji. Shivaji decided to avenge this action. Shaista Khan, living in Shivaji's Lal Mahal in Poona, was also an unbearable thing for Shivaji. Therefore Shivaji made a bold plan to destroy Shaista Khan.
In early April 1663, Shivaji settled in Sinhagad near Poona. On 5 April 1663, Shivaji decorated 1000 of his selected soldiers as processions and came down from Sinhagad at night with them. In broad daylight, this unique procession entered the city of Poona with gaiety. This procession kept on dancing and singing and roaming in the streets of the city till evening. In the evening, 200 soldiers of Shivaji took off the clothes of the procession, dressed like ordinary soldiers, started moving towards the Mughal military camp. When he was stopped by the Mughal guards, he said that he was a soldier of Shaista Khan's army. Since Hindu soldiers were recruited in the Mughal army and Shaista Khan had recruited thousands of Hindu soldiers to fight against Shivaji, no one doubted these soldiers. Bhimsen, an eyewitness to this incident, has written that Shivaji, along with 200 of his soldiers, came on foot for 40 miles and reached near the camp at night.
Shivaji and his soldiers stopped at the rear of the Lalmahal and waited for the night to come. At midnight, he made a hole in the wall of one of the rooms of the palace. Shivaji was familiar with every corner of this palace. When Shivaji lived in this palace, there was a window here, but at this time the wall at that place was masonry. Due to this Shivaji guessed that Shaista Khan would be found with his family in this room. His guess turned out to be right. Shivaji, along with his 200 soldiers, entered the palace through this window and reached near Shaista Khan's bed with a swift sword. Shaista Khan's eyes opened due to the sound. At the same time Shivaji attacked Shaista Khan with a sword. Seeing the enemy soldiers, a maid extinguished the lights of the palace. Due to Shaista Khan's overturn, Shivaji's sword went almost empty, but still his finger was cut. At the same time, the soldiers of Shivaji's procession started playing loudly, so that the soldiers guarding around the palace did not know about the activity going on inside the palace and the Maratha soldiers created a ruckus in the entire palace. Shaista Khan managed to escape taking advantage of the darkness. The soldiers of Shivaji, mistaking Shaista Khan's son Abul Fatah as Shaista Khan, beheaded him and took away with them. A general of Shaista Khan was also killed. In this action, 50 to 60 people of Shaista Khan were injured.
Gradually, the Mughal soldiers understood the whole thing that what had happened, they started gathering outside the palace. Shivaji was also alert, he signaled with a loud sound and his soldiers took Shivaji out of the palace and the Mughal camp. The Mughal soldiers kept searching for the invaders inside the palace and Shivaji was able to get out of Poona safely. There was a military camp of Marwar king Jaswant Singh on the way, but no one could find anything there, so Shivaji did not face any difficulty in escaping from Poona.
Shaista Khan's Badli
The manner in which Afzal Khan was assassinated and what happened overnight in the Lal Mahal of Poona made the Mughals sleepless. For them Shivaji was no less than a mystical power who could reach anywhere, anytime and do anything. Aurangzeb was very angry at this failure of Shaista Khan and instructed him to take up his tent poles and go to Bengal. Shaista Khan too, not considering it appropriate to stay here, left silently.
Role of Jaswant Singh
The escape of Maratha soldiers with the severed head of Shaista Khan's son, in front of the camp of Maharaja Jaswant Singh, the king of Jodhpur, was a suspicious event. This made it popular in the whole country that the inspiration of Maharaja Jaswant Singh was working in this work of Shivaji because Shaista Khan had got Maharaja Jaswant Singh deposed after the war of Dharamat after complaining to Aurangzeb. Contemporary writer Bhimsen says- "Only God knows what is the truth!"
Return of Jaswant Singh
Maharaja Jaswant Singh was sent on a campaign to the south with Shaista Khan, but he did not agree with the campaign being conducted against Shivaji. So he did not get any success. In November 1663, under the leadership of Jaswant Singh, Shivaji's famous fort Sinhagad was attacked. Contemporary writer Bhimsen has written- "Jaswant Singh laid siege to Kondana fort (old name of Sinhagad). The Mughals attempted to climb the walls of the fort. Many Mughals and Rajputs lost their lives in this attack. Many people were also killed by landmines. It became impossible to conquer the fort. Frustrated by the failure, Maharaja Jaswant Singh and Rao Bhausinh Hada lifted the siege from the fort on 28 May 1664 and returned to Aurangabad. Alamgirnama remarks with great regret – “Not a single fort has been captured. The campaign against Shivaji ran into trouble and was tarnished."
Letter by Shivaji to Aurangzeb
After the return of Shaista Khan and Maharaja Jaswant Singh, Shivaji wrote a stern letter to Aurangzeb - "The visionary men know that in the last three years the emperor's eminent generals and experienced officers have been visiting this area. The emperor had ordered them to capture my forts and territories. In his communication to the emperor, he writes that the territories and forts will be captured soon. Even if Kalpana was like a horse, it would have been impossible for her to come to these areas. It is very difficult to conquer this area. They don't know this! He is not ashamed to send false messages to the emperor. In my country there are no places like Kalyani and Bidar, which are situated in the plains and can be captured by attacking. This area is full of mountain ranges. There are 60 forts in this area. Some of them are located on the beach. Afzal Khan brought a strong army, but he was helpless and was eventually destroyed. After the death of Afzal Khan, Amir-ul-Amra Shaista Khan entered my land full of high mountains and deep valleys. He struggled tirelessly for three years. He wrote to the emperor that he would soon conquer my territory. The end of such genuine attitude was expected. He was humiliated and was forced to return. It is my duty to protect my motherland. To maintain your reputation, you send false messages to the emperor. But I am blessed by divine grace. None of the attackers have succeeded in these areas.”