Best way to introduce my anxious dog to kenneling after always letting him roam free?

I have a 3 year old male Transylvanian hound-mix and have had him coming up on nearly 2 years.

The previous owners had him as an outside dog and when I got him, the transition to making him an indoor dog was rough. The biggest issue was that he would constantly “mark” all over the house whenever I was gone. He also has terrible separation anxiety that not only causes him to mark but also tear up pillows and cushions.

I have previously tried to kennel him whenever I leave but he manages to break out every time. After 2 broken kennels I gave up and just let him freely roam the house. I actually gave him the middle name “Houdini” after one night I was so confused as to how he kept breaking out, I zip tied the kennel doors shut and a few hours later I come home to him laying in my bed with a mouth full of my pillow.

I have tried leaving him in one room and he freaked out and started clawing at the door like wild and ended up tearing up carpet all around the door.

Recently I’ve decided to get one of those expensive heavy duty kennels but i’m wondering if this time there’s a better way to make him more comfortable to the idea of going in his kennel whenever I leave. I’m never gone for more than 6-7 hours at a time for work and usually someone else in my house can let him out.

I know he won’t be able to break out of this kennel so i’m mostly worried about making sure he’s comfortable and not barking/whining the whole time.

Any tips would be great thank you

submitted by /u/Remarkable_Party3422
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