 In August 1581 he managed to escape with the connivance, it was suspected, of his gaoler, John Sheriff, clerk of the ordnance.In September 1582 he was reported to have gone to Spain with the catholic bishop of Killaloe; but he was in January 1583 wounded at the Dingle, and in April 1587 captured and committed to Dublin Castle.In 1588 Sir William Herbert made a laudable effort to procure his release, offering to pawn his bond to the uttermost value of his land and substance for his loyal and dutiful demeanour, ‘knowing him to be of no turbulent disposition'.