O'Cahan was
knighted on 20 June 1607. In September, Tyrone and other earls fled the country in what is known as the
Flight of the Earls. In early 1608, O'Cahan's brother joined
the rebellion of
Cahir O'Doherty, and although O'Cahan was not officially implicated, he was suspected of having knowledge of the uprising. He was arrested but never tried. The antiquarian
Francis Joseph Bigger has suggested that he was rumoured to have attempted flight with Tyrone and the other rebel lords, and had only been prevented from doing so by an "accidental delay in crossing some ferry on the road". In the event, O'Cahan remained in
Limavady Castle following Tyrone's flight.
Sir Arthur Chichester—the Crown's
Lord Deputy in Ulster—reasoned, says Bigger, that this indicated not only his sympathy for the rebels but
mens rea also. This was compounded by the fact that, in English eyes, O'Cahan "had become troublesome, and almost unmanageable of late, so, everything considered, it was thought best to take him also into special keeping at Dublin Castle". Bigger notes that, although O'Cahan had remained loyal to his liege lord throughout the latter's seven-year campaign at the Crown, in 1608 he joined the major English statesman and commander in Ireland,
Henry Docwra, on condition that O'Cahan would receive sufficient grants and lands to enable him to establish himself independently of Tyrone, and would no longer hold his estates in
fief. ==Downfall and death==