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Recently my wife and I adopted a 5/6 year old neutered male from the local shelter about 8 weeks ago. We currently have two 10 year old females now. This guy is almost perfect he is a bit stubborn at times, but here is the big thing. I think he has some separation anxiety, we have a 10x20 outdoor kennel that they can stay in when the weather permits. We originally had him separated from the females at first and he wanted to tear the door off every time we leave. After a few weeks we put him with the females and he was better, but now he's getting worse again.

He has broke a bottom canine from this, has had the root canal done, but waiting on the cap now. Some days are good and some days are bad, it seems to last 20 min to an hour according to the cameras. He does fine in the house for short outings like 2-3 hours. Our next step was to leave him in the garage and see how he does in there. To us it seems to be separation issues, since he will go in and out of the kennel fine when your with him, but as soon as your out of sight he wants out now.

Any advice is greatly appreciated. I just don't want him to hurt himself again.
 

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If I understood your post correctly, he does fine for 2-3 hrs. inside the house, fine in the garage, but not in the kennel even though your other dogs are in there with him. So, I think the issue is with the kennel and that may have something to do with how he was treated in his previous homes. Maybe very slow conditioning to the kennel would work as explained in this article:

https://www.whole-dog-journal.com/issues/11_7/features/Canine-Separation-Anxiety_16044-1.html
 

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Crates are my go-to suggestion, but it doesn't always work. I have a friend who had a similar issue and a crate wasn't helping at all. She bought a Guardzilla sec cam so she can talk to her dog. He gets weird, she gives commands via her phone, and it helps him to settle. They work with both Apple and android.
 

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He absolutely will not go in a crate, being new to us and not knowing his background I have not forced it on him. He was fine today, carried on for a few minutes then was fine all day, I'm sure tomorrow will be a different story, lol. I will look into those cameras as suggested.

Thanks
 
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