What does he lie on inside the crate? I just posted a happy experience involving this before I read your post (Easy Crate Introduction). To keep you from looking for it I'll repeat it here. We let our pup sleep on her crate mat the first night sans the crate. Once she had her odor on the mat and claimed it as her bed, she promptly jumped in the crate after it when I placed it inside. Not that it matters but is one of the oval, fuzzy type mats.

Jim