@Darth T,Thanks for posting in Q&A.
To narrow down this problem, please do some checks below.
1.Please check whether the VPP token expire
2.Please try to create a new ADE enrollment profile, select Setup Assistant with Modern Auth and check whether the Company Portal can install automatically.
3.Please try to get a new apple mdm push certificate to check whether the Company portal install automatically.
If there is any unclear, feel free to let me know.
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