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Downfall and death

While Octavian occupied Athens, Antony and Cleopatra landed at Paraitonion in Egypt. The couple then went their separate ways, Antony to Cyrene to raise more troops and Cleopatra to the harbor at Alexandria in an attempt to mislead the oppositional party and portray the activities in Greece as a victory. She was afraid that news about the outcome of the battle of Actium would lead to a rebellion. It is uncertain whether or not, at this time, she actually executed Artavasdes II and sent his head to his rival, Artavasdes I of Media Atropatene, in an attempt to strike an alliance with him.

Lucius Pinarius, Mark Antony's appointed governor of Cyrene, received word that Octavian had won the Battle of Actium before Antony's messengers could arrive at his court. Pinarius had these messengers executed and then defected to Octavian's side, surrendering to him the four legions under his command that Antony desired to obtain. Antony nearly committed suicide after hearing news of this but was stopped by his staff officers. In Alexandria he built a reclusive cottage on the island of Pharos that he nicknamed the Timoneion, after the philosopher Timon of Athens, who was famous for his cynicism and misanthropy. Herod, who had personally advised Antony after the Battle of Actium that he should betray Cleopatra, traveled to Rhodes to meet Octavian and resign his kingship out of loyalty to Antony. Octavian was impressed by his speech and sense of loyalty, so he allowed him to maintain his position in Judea, further isolating Antony and Cleopatra.

Cleopatra perhaps started to view Antony as a liability by the late summer of 31 BC, when she prepared to leave Egypt to her son Caesarion. Cleopatra planned to relinquish her throne to him, take her fleet from the Mediterranean into the Red Sea, and then set sail to a foreign port, perhaps in India, where she could spend time recuperating. However, these plans were ultimately abandoned when Malichus I, as advised by Octavian's governor of Syria, Quintus Didius, managed to burn Cleopatra's fleet in revenge for his losses in a war with Herod that Cleopatra had largely initiated. Cleopatra had no other option but to stay in Egypt and negotiate with Octavian. Although most likely later pro-Octavian propaganda, it was reported that at this time Cleopatra started testing the strengths of various poisons on prisoners and even her own servants.

Cleopatra had Caesarion enter into the ranks of the ephebi, which, along with reliefs on a stele from Koptos dated 21 September 31 BC, demonstrated that Cleopatra was now grooming her son to become the sole ruler of Egypt. In a show of solidarity, Antony also had Marcus Antonius Antyllus, his son with Fulvia, enter the ephebi at the same time. Separate messages and envoys from Antony and Cleopatra were then sent to Octavian, still stationed at Rhodes, although Octavian seems to have replied only to Cleopatra. Cleopatra requested that her children should inherit Egypt and that Antony should be allowed to live in exile in Egypt, offered Octavian money in the future, and immediately sent him lavish gifts. Octavian sent his diplomat Thyrsos to Cleopatra after she threatened to burn herself and vast amounts of her treasure within a tomb already under construction. Thyrsos advised her to kill Antony so that her life would be spared, but when Antony suspected foul intent, he had this diplomat flogged and sent back to Octavian without a deal.

After lengthy negotiations that ultimately produced no results, Octavian set out to invade Egypt in the spring of 30 BC, stopping at Ptolemais in Phoenicia, where his new ally Herod provided his army with fresh supplies. Octavian moved south and swiftly took Pelousion, while Cornelius Gallus, marching eastward from Cyrene, defeated Antony's forces near Paraitonion. Octavian advanced quickly to Alexandria, but Antony returned and won a small victory over Octavian's tired troops outside the city's hippodrome. However, on 1 August 30 BC, Antony's naval fleet surrendered to Octavian, followed by Antony's cavalry.

Cleopatra hid herself in her tomb with her close attendants and sent a message to Antony that she had committed suicide. In despair, Antony responded to this by stabbing himself in the stomach and taking his own life at age 53. According to Plutarch, he was still dying when brought to Cleopatra at her tomb, telling her he had died honorably and that she could trust Octavian's companion Gaius Proculeius over anyone else in his entourage. It was Proculeius, however, who infiltrated her tomb using a ladder and detained the queen, denying her the ability to burn herself with her treasures. Cleopatra was then allowed to embalm and bury Antony within her tomb before she was escorted to the palace.

Octavian entered Alexandria, occupied the palace, and seized Cleopatra's three youngest children. When she met with Octavian, Cleopatra told him bluntly, "I will not be led in a triumph" (Ancient Greek: οὑ θριαμβεύσομαι, romanized: ou thriambéusomai), according to Livy, a rare recording of her exact words. Octavian promised that he would keep her alive but offered no explanation about his future plans for her kingdom. When a spy informed her that Octavian planned to move her and her children to Rome in three days, she prepared for suicide as she had no intentions of being paraded in a Roman triumph like her sister Arsinoe IV. It is unclear if Cleopatra's suicide on 10 August 30 BC, at age 39, took place within the palace or her tomb. It is said she was accompanied by her servants Eiras and Charmion, who also took their own lives.

Octavian was said to have been angered by this outcome but had Cleopatra buried in royal fashion next to Antony in her tomb. Cleopatra's physician, Olympos, did not explain her cause of death, although the popular belief is that she allowed an asp or Egyptian cobra to bite and poison her. Plutarch relates this tale, but then suggests an implement (κνῆστις, knêstis, lit. 'spine, cheese-grater') was used to introduce the toxin by scratching, while Dio says that she injected the poison with a needle (βελόνη, belónē), and Strabo argued for an ointment of some kind. No venomous snake was found with her body, but she did have tiny puncture wounds on her arm that could have been caused by a needle.

Cleopatra decided in her last moments to send Caesarion away to Upper Egypt, perhaps with plans to flee to Kushite Nubia, Ethiopia, or India. Caesarion, now Ptolemy XV, would reign for a mere 18 days until executed on the orders of Octavian on 29 August 30 BC, after returning to Alexandria under the false pretense that Octavian would allow him to be king. Octavian was convinced by the advice of the philosopher Arius Didymus that there was room for only one Caesar in the world. With the fall of the Ptolemaic Kingdom, the Roman province of Egypt was established, marking the end of the Hellenistic period. In January of 27 BC Octavian was renamed Augustus ("the revered") and amassed constitutional powers that established him as the first Roman emperor, inaugurating the Principate era of the Roman Empire.