Óláfr appears to have held authority on the island of Lewis and Harris. At some point, Óláfr appears to have confronted Rǫgnvaldr for a larger stake in the kingdom, after which Rǫgnvaldr had him seized and imprisoned by the King of Scotland. Upon his release in 1214/1215, Óláfr is stated to have undertaken a pilgrimage to Santiago de Compostela, after which the half-brothers were reconciled, and Rǫgnvaldr had Óláfr married to Lauon, the sister of his own wife. In what appears to have been a politically motivated maneuver, Óláfr had his marriage nullified by Reginald, Bishop of the Isles, and proceeded to marry Cairistíona, a daughter of Fearchar mac an tSagairt. Whilst Lauon appears to have been a member of Clann Somhairle, a kindred led by Ruaidhrí mac Raghnaill, a man closely aligned with Rǫgnvaldr and opposed to the Scottish Crown, Cairistíona was the daughter of a rising Scottish magnate.