 He appears to have entered Scotland in 1424 after King James I of Scotland returned from his eighteen-year period as a hostage in England; it is notable and certainly relevant that James' queen, Joan Beaufort, was the niece of Henry Beaufort, Bishop of Winchester.After entering Scotland, James was chaplain and secretary to the king, who bestowed on Winchester Alyth in Angus and helped him become Chancellor of Dunkeld.Winchester was out of Scotland in 1432, attending the Council of Basel on behalf of King James; he was also Clerk of the Register in this year.