Don't beat yourself up over it too much. We all make mistakes. How old is Oliver?
How much do you keep him in the crate during the day? Is the issue that you want him to sleep in the crate at night, or that you want him in the crate during the day, or both?
I suggest leaving the crate door open for now so that he can go in and out freely. You can also put a nice treat in there that is a crate-only treat, like kong with peanut butter.
If he is already potty trained, you might consider letting him follow you around the house. Yorkies like to be with you all the time. OR, put the crate somewhere where it's easier for him to see you.
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