VPP apps not delivering, iTunes users required to input password

I'm testing a pilot with Dell EMM and my Apple DEP devices are enrolled correctly and getting free apps. However, my paid app (VPP purchase) is not getting pushed out. 

The Dell EMM user has all 30 devices. Each device has it's own iTunes account. I was able to register one device's Dell EMM user with the VPP registration link to accept apps from the VPP account.

I'm also not sure why the iTunes password is required for each push. I was under the assumption that DEP + MDM + VPP enrollment meant you didn't have to do that.

I'm not sure what else I'm missing. I've done this a few times with Filewave and haven't had any issues.

We don't have a K---- appliance demo yet. Just the cloud mobility manager.

Thanks for any advice.

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