Here is what we tell people when they adopt at the shelter. Leave the door of the crate open and feed him his meals in the crate (with the door open). Do that for a week or so. Then just start putting him in the crate with the door just held closed for a minute. Gradually increase the amount of time he stays in there. Then put him in, close the door and leave the room. Baby steps like this.
BUT, the most important thing is consistency and don't give in to that cute little face!
Maybe other people will have other ideas for you to try as well.
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