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The main rule is don't open the crate while he's crying. I would put him in with something to work on (chewy, stuffed kong, etc), then shut the door and walk around the house doing chores or something for half an hour. If the puppy cries I just wander around the house doing my thing and ignoring them. Sometimes it means I come in the room and if they stop crying I might praise and then continue on my way. Eventually most puppies settle down and realize that you're not going anywhere, but you're not going to pay attention to them right now either.

How easy this is often depends on the puppy. Some cry because you are out there having fun and they want to come and have fun too. These puppies usually cry for 5 min or so and then settle down when they realize you're not going to let them out. Other puppies have actual anxiety about the whole thing and it is really hard for them, and it can take a while. With these puppies I do think making them cry it out can make things worse, but at some point though you're going to need to leave the house and crate the puppy for a while. I work and I can't stay home with my dog forever only leaving him alone for 2 min at a time. My older dog is like this, and while he doesn't like to be crated if I'm not home he's fine crated while I'm around and he's fine loose in the house while I'm gone. When he was too little to be loose in the house we just sucked it up and crated him with kongs and things to keep him busy. My current puppy is absolutely fine in the crate, almost zero crying, and she's always been that way, so a lot of it is personality.

Also, I think it's totally fine for him to sleep on your lap while you're in the room, if you're ok with it. Work on being alone, but you can also be affectionate and cuddly when you're there.
 
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