For the next three or four months, Oswald was but little at the castle; Percy utilizing his services, in the manner most agreeable to him, by sending him on errands to various knights and gentlemen, in different parts of Northumberland, and to the fortified places held by the English across the Border.

A fortnight after his contest with Sinclair, Sir Henry formally appointed him one of his esquires.
"You are young," he said, "for such a post; but as you have shown that you are well able to take care of yourself in arms, and as I perceive you to be shrewd and worthy of confidence, your age matters but little.
As my messenger, you will be more useful travelling as one of my esquires, than as one without settled rank; and I can not only send written communications by you, but can charge you to speak fully in my name, and with my authority." Oswald was not slow in finding out the advantages that the position gave him.

On the first errands on which he had been sent, he had been treated as but an ordinary messenger, had been placed at dinner below the salt, and herded with the men-at-arms.

As an esquire of Lord Percy, he was treated with all courtesy, was introduced to the ladies of the family, sat at the high table, and was regarded as being in the confidence of his lord.

His youth excited some little surprise, but acted in his favour, because it was evident that Percy would not have nominated him as one of his esquires, had he not shown particular merit.