Cyrenna was born in 490, the only daughter of Alyn Serry and Mariya Hewett. Her mother's pregnancy was difficult, and ultimately ended in a swift death due to childbed fever. The newborn Cyrenna fell ill soon after. While she recovered due to the intervention of the house's Maester, she lost the use of her right eye and her voice was permanently reduced to a harsh whisper.
At the age of six, Cyrenna was sent to foster under her father's younger sister, Elinor Serry. A notoriously difficult child, Cyrenna spent most of her first year running and hiding rather than speaking to anyone. Eventually, and with much coaxing, she learned how to hunt and hawk and play the high harp. She refused to learn how to sing or recite.
Cyrenna attended the wedding of Elinor Serry and Godric Grimm as her aunt's handmaiden. She was the last person to dance with Tristan Serry before his death. As her father, Alyn, was the closest male relative, he inherited the Lordship of Southshield. Cyrenna was called back to keep her father's hearth on the eve of the War of the False King.
Longwatch was razed during the Siege of Southshield. Cyrenna and Lord Alyn were held hostage, first in a royalist camp, and then at Old Oak once it was taken by crown forces. During her captivity at Old Oak, Cyrenna became close friends with Ser Domeric Inchfield. At the end of the war, House Serry swore fealty to the Iron Throne and Lady Paramount Ashara Lannister. Cyrenna and her father returned to Southshield.
House Serry began the arduous process of rebuilding Southshield. In 506, Lord Alyn married Carellen of the Shield Coast, the daughter of a wealthy knight, two years Cyrenna's senior.
House Serry continued to rebuild. In 508, Carellen announced a pregnancy, thus making Cyrenna the heir presumptive. During the Appleton Tourney (508 AC), Cyrenna lost her maidenhead to Domeric Inchfield after his public engagement to Ceryse Fossoway. She was sent home to Southshield in disgrace, and from there to Oldtown to become a lady-in-waiting to Ashara Lannister, Lady Paramount of the Reach.
Near the end of the sixth era, Cyrenna travelled with Ashara and her retinue to King's Landing, where she met the lady paramount's brother and his children for the first time. While her ladyship met with her brother behind closed doors, Cyrenna spent her time with little Loras and explored the gardens of the Red Keep.
Upon her return to the Hightower, Cyrenna learned of Ceryse Fossoway's pregnancy which sent the girl into a sulky mood for the rest of the era.
As winter approached, Cyrenna recovered from her sadness at the happy thoughts of the change of the weather.
Lord Alyn Serry, father
Lady Mariya Serry, mother (deceased)
Lady Carellen of the Shield Coast, stepmother
Elinor Serry, aunt
Alicent Serry, aunt
Tristan Serry, cousin (deceased)