 By the age of about 20 he had been knighted, and in October 1405 he was granted safe conduct by Henry IV of England to attend a tournament in London.He spent the next few years 'constantly passing to England, either as a commissioner for truce, as a hostage, or on diplomatic business'.Possibly in recognition of his role as hostage on his behalf, he was granted the Barony of Hawick by his cousin Archibald, 4th Earl of Douglas, in 1407.