After Pain's death in 1137, Sybil attempted to retain control of Ludlow and her lands but in 1139 King Stephen of England married her to Josce de Dinan, who died in 1166.
Sybil's marriage to Josce, and his control of Ludlow in right of his wife forms the background to a medieval Welsh romance, Fouke le Fitz Waryn.
One theory, given in the entry for her first husband in the Oxford Dictionary of National Biography states that Sybil was the niece of Hugh de Lacy.
Sybil had inherited lands that originally had been held by her kinsman Roger de Lacy, who had been banished from England in 1095 and his English estates confiscated; he had though retained his properties in Normandy.
[10] On Roger's death his son Gilbert inherited the lands in Normandy, and pressed his claim to the family's former English estates.
Coplestone-Crow notes that there was uncertainty hanging over the inheritance, and accounted for one reason why Sybil's husband worked to secure more lands around Ludlow.
[3] Stephen also settled the bulk of Pain's lands on Cecily, which led to disturbances and a minor war among disappointed claimants.