That is a good idea to spend more time w/ him in the kennel. He probably feels "unwanted" & lonely there. You want the kennel to be a happy place. when he does enter the kennel praise him. Also do not give him the chance to escape, keep him on a lead until he is in the kennel. Keeping something w/ your scent in there may help too. Play a game in the kennel, make him do a few commands & remember to praise when he cooperates. Give him a kong toy in there to keep him occupied for a little while. Good luck!