My Shadow wasn't too hard to crate train...! I was very Lucky lol! The first 4 nights, it was hell. He was howling non-stop ALL night. But i hanged in there, and now, he's going by himself in his crate when it's bedtime!!
Some tips i used:
-I put his crate in my bedroom, next to my bed.
- I put a blanket on his crate to make him more "secure".
- And most importanty, i didn't speak to him or giving attention when he was howing!!!
So, all-in-all, it took Shadow 4 nights!