What is known about Hkonmaing is solely from the Burmese chronicles. The Chinese annals on the Tai-Shan frontier stopped at Hsenwi, and make no mention of Hsipaw. The Burmese chronicles mention Hkonmaing as a supporting figure—albeit an important one—in King Narapati II's reign. According to the chronicles, Hkonmaing was the ruler of the Shan state of Onbaung–Hsipaw, certainly by 1505. Since his eldest son Hkonmaing the younger was born in 1497, he was likely born c. 1480. At the time, Onbaung–Hsipaw was a major Shan state, which controlled the entire stretch of eastern Shan Hills west of the Salween river: Bhamo, Yawnghwe, Mong Nai and Mong Pai. Moreover, Onbaung–Hsipaw's relationship with Ava in the early 16th century was closer to an alliance than a patron-client arrangement. Chronicles mention Hkonmaing and Narapati II as thwethauk brothers—men who have ritually entered into "a sacramental brotherhood" by drinking each other's blood. Ava had been disintegrating since the 1480s, and its rulers had been fighting losing wars on several fronts against its former vassal states. Narapati II, who came to power in 1501 amidst major rebellions, desperately tried to retain the loyalty of remaining "vassal" rulers like Hkonmaing of Onbaung and Mingyi Nyo of Toungoo.
Ally of Ava
In the end, Hkonmaing was the only steadfast ally of Narapati II. In late 1505, he sent an army led by his younger brother to assist Narapati defend the town of Sale from the forces of Prome and Toungoo. Hkonmaing likely stayed in the alliance because he and Narapati were fighting against a common enemy: Sawlon the ambitious expansionist leader of Mohnyin. Sawlon had been raiding Ava's northern territory since 1502. In 1511, Hkonmaing lost Bhamo, its northernmost possession, to Sawlon whose army simply seized the border town between the two Shan states. Hkonmaing asked Narapati for help. Narapati sent a sizable army. But the Ava army was ambushed en route at Myedu by a smaller Mohnyin force, and was driven back with heavy losses. Hkonmaing remained in the alliance even as Mohnyin grew more powerful in the following years. When Sawlon and his allies attacked Ava itself in 1524, Hkonmaing personally led an army and defended Ava. But the combined Mohnyin and Prome forces drove out Narapati II and Hkonaming on 22 March 1525. The two thwethauk brothers still had sizable armies—the defeated Ava army still had 8,000 men, 400 horses, 250 elephants while the Onbaung army counted 7,000 men, 500 horses, 80 elephants. As the two armies moved south and entered Toungoo's territory, they were met by the Toungoo army at Yamethin. They defeated the Toungoo army, and followed up to Toungoo itself. They could not take it and had to retreat to Ava. According to the chronicles, Narapati was truly grateful that Hkonmaing remained loyal till the end, and is said to give the saopha many jewels. But Hkonmaing is said to have refused the presents. But their troubles were not yet over. Sawlon returned in the dry season of 1526–27 with a 15,000-strong army. Hkonmaing again came to the aid of Narapati II, and defended Ava. Like in 1525, Sawlon's forces overwhelmed Ava's defenses. On 25 March1527, Narapati II died in action, and Ava was taken. Sawlon appointed his eldest son Thohanbwaking of Ava.
Later years
After the defeat at Ava, Hkonmaing retreated to Hsipaw. He later either agreed to a truce with, or submitted to Sawlon since Sawlon did not attack Hsipaw after Ava's fall. After Sawlon was assassinated in 1533, Hkonmaing like other leaders of the Confederation probably did not acknowledge Thohanbwa as the first among equals. However, he did stay in the Confederation. He actively participated in the Confederation's 1541–42 campaign to retake Prome. The campaign was a failure. The Confederation forces were defeated in April 1542 by Toungoo forces led by Gen. Bayinnaung. Hkonmaing died during the campaign or shortly after since by May 1542, he was already dead.