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The first time we got our pup, he would cry when we leave him outside of the bedroom. We simply put him in the kennel and leave it in the room while we sleep. No clothes or ticking clock needed, the dog could sense you nearby and that's all good.
For separation anxiety (barking and whining when you're away), we would occasionally put him in the kennel for no reason at all. Keep in mind that the kennel should be a happy place for the dog, don't use it as a mean of punishment. Then we would leave the room and come back. Ignore the whining. Do not address him or even look at him. Act like nothing happen. You can gradually extend the away time.
Also don't make a habit of letting the dog out in the middle of the night to go pee. He should know to do his business whenever you take him out. We start out by taking him out for a short walk every 1 or 2 hour. Then we extend the time between walks. Praise him like no tomorrow whenever he goes outside.
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