@Jon Resele, Thanks for posting in Q&A.
For your issue, please ensure the dynamic rule syntax is correct, and you can validate it follow the link below.
https://learn.microsoft.com/en-us/entra/identity/users/groups-dynamic-rule-validation
The official documentation also points out that you should reduce the use of Contain and Match as much as possible to achieve better results.
https://learn.microsoft.com/en-us/entra/identity/users/groups-dynamic-rule-more-efficient
Also, you can consider change the displayName and ownership to an easy one or consider the Consider other device attributes for filtering
Here is a link containing the device attributes that you can refer to.
https://learn.microsoft.com/en-us/entra/identity/users/groups-dynamic-membership#rules-for-devices
Hope above information can help you, if there is any update, feel free to let me know.
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