Our puppy cried terribly the first night, and my husband slept with his fingers through the gate (of the crate) all night. After a couple nights, she was fine. Of course your dog will cry the first night. He misses his mother and sibs. It takes a little while for them to get used to being alone. Ours slept in her crate for nearly two years, but once we knew she was well trained, she has been in our bed ever since. Unfortunately we have nights like last night when she threw up on the quilt in the middle of the night and got up later to go out, (Boy am I tired today!) but crate training works. I have not used a playpen with mine. I tried it with a bigger puppy once and came home to find her running around the house. She had chewed the netting!