Caught up in conspiracies caused by the Flight of the Earls and angered by the confiscation of his lands for the Plantation of Ulster, in 1608 Sir Cahir sacked and burned the town of Derry and Cahir's foster-father Felim Riabhach McDavitt (Mac Daibhéid) killed Docwra's successor as Governor, Sir George Paulet, with whom Cahir had repeatedly quarreled. Paulet was accused by some of goading O'Doherty into rebellion by a series of insults, and was also said to have assaulted him. Niall Garve O'Donnell, previously a loyal supporter of the English Crown, was also accused of supporting the rebellion. O'Doherty's precise motives for the rebellion are unclear, and its timing is also something of a puzzle, especially as the Privy Council of Ireland had just ordered that the remainder of his lands be restored to him. Taking revenge on Paulet was perhaps a sufficient motive in itself.