Her father fell at the battle of Rovine (1395), while fighting as a vassal of Ottoman sultan Bayezid I against Mircea I of Wallachia.

[6] When her spouse Manuel II was absent in 1393, he made his mother regent in his absence rather than his wife.

The fact that she made monastic vows did not necessarily mean that she had to leave the court and enter a convent.

In 1439, when John VIII was in Italy, he was informed that the patriarch of Constantinople had died, but he refused to appoint a new one until he could consult his mother.

[11] Empress dowager Helena Dragaš is known for her interest in ecclasiastical issues, and she was a prominent figure in the anti-unionist court fraction that opposed the proposed union between the Orthodox and Catholich church, which was a major political issue during the reign of John VIII, and for her conflict with the pro-union fraction.

[13] Eventually, she did give her consent, or at least decided to no longer actively oppose, the union of churches, which was the wish of her son John VIII.

She served as regent after the death of her son John VIII in 1448, until the arrival of his successor Constantine XI from Mistra in 1449[15] She eventually persuaded Sultan Murad II to intervene in Constantine's favour, leading to his assumption of the throne in January 1449.

[19] She is venerated by the Orthodox Church as a saint, and her memory is commemorated on 29 May, the day of the Fall of Constantinople to the Ottomans and of the death of her son Constantine XI.