When the peace between the Safavids and the Ottomans collapsed and the Turkish general Lala Mustafa Pasha drove the Persians out of Georgia in 1578, it roused the Safavids to come to take further action.
Then incumbent Safavid king Mohammad Khodabanda wanted a puppet ruler in Kartli that was popular amongst the local population.
Therefore, he ordered for Simon I to be released from prison and offered him the crown of Kartli on the demand that he would convert to Islam.
Having been imprisoned for nine years, Simon I's resolve was weakened.
In the same year he accepted the Safavid king's demands, and, in order to invade Tbilisi, he received cannon and 5,000 Qizilbash soldiers led by general Ali-Qoli Khan.
Simon led a successful guerilla war against the Turks, recovered most of Kartli by 1579, and put a siege to Tbilisi.
At the same time, he induced the prince Manuchar II Jaqeli to revolt against the Ottoman rule in Akhaltsikhe, and attempted to get support from Pope Clement VIII, Emperor Rudolph II and Philip II of Spain.
The negotiations, however, failed to yield any serious results.

In 1580 Simon I repulsed Ottoman invasion of Kartli, and in 1582 defeated main Ottoman army on the field of Mukhrani, which had a lasting impact as Ottomans were at the height of their power and such a defeat shuttered the myth of their invincibility.
Simon I's Persian monolingual seal of the same period reads: "Allah, who has no equal, knows that Semiyun (Simon) is a slave of the Shah from the bottom of his heart, 933 (1585)".

From 1588 to 1590, Simon interfered on three occasions into a power struggle in the western Georgian kingdom of Imereti, and though victorious over Levan of Imereti at the Battle of Gop'anto (1588), he was finally defeated at Op'shkviti and driven out with the help of the Turks.
Finally, the Ottomans prevailed and their recently appointed commander, Ferhad Pasha, was able to conquer Kartli by 1588.
Simon had to make peace with the Sublime Porte and agreed to pay an annual tribute.
By a peace treaty signed in Constantinople on March 21, 1590, the Safavids also recognised all of Georgia as an Ottoman possession.
Simon, however, resumed his struggle against the occupants in 1595, and retook Gori after a long-lasting siege in 1599.
The sultan Mehmed III sent a large punitive force led by Jafar Pasha, beylerbey of Van.
Simon met it at the Battle of Nakhiduri, but he was severely defeated and taken captive while retreating, 1599.

Upon the Simon's arrest the Sultan Mehmed III made the following order:
From Morocco to the Caspian Sea, from the Caucasus to the Persian Gulf, I order to exhibit the carpets in all of my realm and to celebrate for 3 days the arrest of King Simon.

Simon was sent to Constantinople where the Georgian noblewoman Gulchara was brought to care for the aged king.
He died in 1611 as a prisoner at the Fortress of the Seven Towers (Yedikule) without converting to Sunni Islam, shortly before the cessation of the Ottoman–Safavid hostilities.
His body was then redeemed by the Georgians and buried at the Svetitskhoveli Cathedral at Mtskheta next to his father.
When the peace between the Safavids and the Ottomans collapsed and the Turkish general Lala Mustafa Pasha drove the Persians out of Georgia in 1578, it roused the Safavids to come to take further action. Then incumbent Safavid king Mohammad Khodabanda wanted a puppet ruler in Kartli that was popular amongst the local population. Therefore, he ordered for Simon I to be released from prison and offered him the crown of Kartli on the demand that he would convert to Islam. Having been imprisoned for nine years, Simon I's resolve was weakened. In the same year he accepted the Safavid king's demands, and, in order to invade Tbilisi, he received cannon and 5,000 Qizilbash soldiers led by general Ali-Qoli Khan. Simon led a successful guerilla war against the Turks, recovered most of Kartli by 1579, and put a siege to Tbilisi. At the same time, he induced the prince Manuchar II Jaqeli to revolt against the Ottoman rule in Akhaltsikhe, and attempted to get support from Pope Clement VIII, Emperor Rudolph II and Philip II of Spain. The negotiations, however, failed to yield any serious results.
In 1580 Simon I repulsed Ottoman invasion of Kartli, and in 1582 defeated main Ottoman army on the field of Mukhrani, which had a lasting impact as Ottomans were at the height of their power and such a defeat shuttered the myth of their invincibility. Simon I's Persian monolingual seal of the same period reads: "Allah, who has no equal, knows that Semiyun (Simon) is a slave of the Shah from the bottom of his heart, 933 (1585)".
From 1588 to 1590, Simon interfered on three occasions into a power struggle in the western Georgian kingdom of Imereti, and though victorious over Levan of Imereti at the Battle of Gop'anto (1588), he was finally defeated at Op'shkviti and driven out with the help of the Turks. Finally, the Ottomans prevailed and their recently appointed commander, Ferhad Pasha, was able to conquer Kartli by 1588. Simon had to make peace with the Sublime Porte and agreed to pay an annual tribute. By a peace treaty signed in Constantinople on March 21, 1590, the Safavids also recognised all of Georgia as an Ottoman possession. Simon, however, resumed his struggle against the occupants in 1595, and retook Gori after a long-lasting siege in 1599. The sultan Mehmed III sent a large punitive force led by Jafar Pasha, beylerbey of Van. Simon met it at the Battle of Nakhiduri, but he was severely defeated and taken captive while retreating, 1599.
Upon the Simon's arrest the Sultan Mehmed III made the following order:
From Morocco to the Caspian Sea, from the Caucasus to the Persian Gulf, I order to exhibit the carpets in all of my realm and to celebrate for 3 days the arrest of King Simon.
Simon was sent to Constantinople where the Georgian noblewoman Gulchara was brought to care for the aged king. He died in 1611 as a prisoner at the Fortress of the Seven Towers (Yedikule) without converting to Sunni Islam, shortly before the cessation of the Ottoman–Safavid hostilities. His body was then redeemed by the Georgians and buried at the Svetitskhoveli Cathedral at Mtskheta next to his father.
Simon I of Kartli