Whats the best way to crate-train a puppy?!?
The problem is you are not ignoring him well enough. He has learned that if he persists enough you give in. Since you have been giving in, it will take even longer now to break this habit. Place the dog in his kennel, give him a treat or verbal praise and then walk away and go to bed. Ignore him when he whines and bangs on his crate. Do not talk to him, yell at him, go to him, or let him out. Completely ignore him. If you give in even if its 2 hours later you are teaching him that you will give in. For some dogs they may cry for hours and hours. We had a foster that literally cried through the entire night, the first night, the whole eight hours. We did not let him out until just over 9 hours when he finally quited down. We then kept him active all day. After a night of no sleep and an active day, it only took an hour the next night for him to quiet down and by the end of the week he didn’t whine at all. It is a battle of wills and the more you give in the longer it will take to train