@NotAStingRayIPromise Thanks for posting in our Q&A.
To avoid any misunderstanding, please tell us how did you enroll device into Azure AD. Did you click on "join this device to Azure Active Directory" under Settings > Accounts > Access work or school? Or any other methods?
Please check if there is any error message under Applications and Services Logs/Microsoft/Windows/DeviceManagement-Enterprise-Diagnostics-Provider/Admin in event viewer.
If there is anything update, feel free to let us know.
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