[jester's mom]

When I put my dogs into their crates I always give them a treat, a nice soft chewy treat, they soon are happy to get in. Having said that, it does take a little while for the pup to learn that making noise is not going to get them "out". It is a new and, to them, scary situation. I have found that letting the pup learn that all that noise is not going to get them anything, after a few nights they settle in and get to understand the routine. If your pup is not soiling during the night, I would not let him out in the middle of the night for making a lot of noise as this will only ingrain this action as ok to do.

Also, one thing I have found that is very helpful in teaching the pup not to be over anxious in their crate, is when I do get up or get home and go to open the crate to let the pup out, if it is whining and bouncing against the door and going nuts to get out, I tell the pup to Shhh or say "quiet" and tap the door whenever they jump against it and when the pup sits back and is quiet for a few seconds, then I let them out. I make them sit quietly a little longer over time and it doesn't take long for the pup to realize that making noise and bouncing does not get them out, but sitting and waiting quietly does. This also seems to teach them to be more calm and quiet in general in the crate.

It may take a few nights of broken sleep, but he should learn in not too many nights that making noise doesn't help. To me, that is the worst part of a new puppy, those few nights of hearing them complain.
Good luck with your little darling!