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Try working your way up. First put your dog in the crate and stay in the room with him for five minutes. Give him treats and praise. Then, do it again, but with short breaks of no attention in between praise and treats for another 5 minutes. Then do it for 10 minutes with you still in the room. When you get up to a solid 30 minutes with you not giving him any attention but staying in the room, leave the room for 5 minutes. If he doesn't cry, reward him immediately. Then work your way up. You can put a blanket over his crate, play soft music or turn on the TV, or give him a bone (one that he can't choke on or swallow) to chew on while you're gone. Be patient.

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