The puppy will most likely cry the first night because it has learned that whining earns attention. Regardless of the whining, you should still be crate training. It is important not to give into the whining so that your puppy learns that it’ll have to stay in the crate; in other words, do not get your puppy out of the crate while it’s whining! If the puppy starts to whimper after a few hours of sleep, however, it’s is most likely telling you that it needs to potty. Take it outside and straight back to the crate so that it does not think it’s time to play. Don’t worry – in most cases, the whining only lasts for one or two nights.
To make the puppy more comfortable, you can fill an empty two-liter soft drink bottle with warm to hot water, wrap it in a towel, and place it in the crate so the puppy feels like it’s sleeping next to a litter mate. Other than the water bottle, however, I do not recommend putting anything in the crate, lest the puppy plays rather than sleeps.