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Every hour on the hour until he's older and with bedtime being the exception. When you can't watch him crate him despite his tantrum he will learn if you ignore him no matter how it breaks your heart- he'll be fine:)If you refuse to crate train him because he throws a tantrum he will quickly learn to be rude in other situations because you are reinforcing whining, yipping, and barking get him what he wants.
I agree with this. Some pups throw some pretty massive tantrums, but you just have to ignore it and let it go on. I usually find it best if I leave the room, so there's no audience for the tantrum. Small puppies sleep alot, so if I can get my pup out for several hours and really wear them out...chances are the tantrum will not be long. When I picked up my most recent puppy, he was awake the drive home, We took him to dinner with us, played with him in the yard, and right before bed put him in the crate with a bully stick. He pitched a fit for about 20 minutes. Then he fell asleep. Within 3 days he was good to go. As long as you NEVER reinforce the tantrum...the dog will adjust. My dogs are all very content in their crates.

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We crated him last night, all night. Put him in at midnight, took him outside every two hours. Let him out and gave him breakfast at 7. Man he pitched a fit last night. It's not whimpering. It's not crying. It's screaming and howling. The little guy has some lungs on him. There were some chunks of quiet, but it pretty much went on all night.

We're going to try again tonight. It was easy to get him in the first time with a kong... it got harder after that. He didn't really want to be in there.
I promise they get over it. Like Selzer said, special treats they only get in their crate really help. It's a fairly natural response for a puppy that's had free reign of the house to pitch a full on fit. As far as they know they're trapped. A trapped puppy screams until Mom comes to help it. If he can see you he may not understand why you're not getting him out (especially if you've done it before). Maybe you didn't hear him?? ;)

Hang in there. :)
 

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So here's my question... if we're crating at night, we still have to let him out to go potty. Does he associate that with "winning" even if he's going right back in?
No. I don't think so.

The important thing is to be sure not to play/give attention to him when he's out. Usually when I have to get up in the middle of the night with puppy I am bleary eyed and cranky to start with. I pick up the puppy, take him out, stand in one spot or do the slow circle thing. I don't pet the puppy, I don't make eye contact with the puppy, I don't talk to the puppy...except to praise him for going potty...and then I pick the puppy back up, trudge back upstairs, put the puppy in the crate with a treat, drop my hand back by the crate and attempt to go to sleep again.
 

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So you don't praise them after you open the gate? Last night I waited until he calmed down every time I let him out, praised him, took him out to pee, put him back in and went back to bed.
If you praise him at all (which I don't usually at night) it should be when he is in the crate. Dogs are very present minded...if you are praising him when he comes out of his crate...well you are rearding him for being out of the crate, not in the crate. If you want to praise and reward him for being quiet in his crate, I would praise and pop a treat through the crate and then walk away again and NOT let him out. Also just being let out of the crate is a reward, he doesn't need an additional dose of praise.
 
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