Ahhh okay, I think I understand what is going on right now.
Let me see if I correctly understand though.
You set them up once to get them enrolled into Meraki and then reset them to trigger the count down.
These iPads are currently factory reset and waiting to be set up again. Though when you set one up from this state it isn't changing from Assigned to Pushed, if it's been more than 30 days it "should" push out the profile.
I also assume you are not using Apple Business Manager or Apple School Manager for managing your iPads as this changes how the iPads interact with Meraki through ADE. I use ASM so our devices are automatically assigned to us when we purchase them from Apple, this makes things so much easier than having to go through the claim process.
Are these iPads on a specific iPadOS or have you not see this make a difference for your troubleshooting?
I would definitely try one iPad and see if setting it up, resetting and then setting it up again changes the status.
Found this helpful? Give me some Kudos! (click on the little up-arrow below)