You should ask him C how he is feeling, B wouldn't work because he would know that you saw how he is feeling and make him even more upset. A would make him angry as you don't even know why he is upset. and D would make him think you don't even care.
I think his name was Lyndon. Anyway, when Lyndon tried to smuggle letters out with released men, he found out that the letters he tried to send with his friends that were free from prison were not sent. The released men were searched and the found letters were read and confiscated.