At night, we bring our pup into our room, and then we cover his crate with a towel or two. We pet him, letting him know we are around and then turn off the lights. He whined a for a few minutes the first few times, but then got the hint and went to bed. In fact, we partially cover the crate every time we put him into the crate for his naps.
Good luck.
I've also remember hearing about placing something under his bed with a ticking sound. It's comforting for young pups, suppose to remind them of mom or other dogs heartbeat.
-Gio
