Dear Kyle G. Russell,
Greetings!
Thanks for reaching out to this community.
Based on your description, I understand your issue with assigning Teams Phone Standard license to a on-prem group.
According to Assign or unassign licenses to a group in the Microsoft 365 admin center - Microsoft 365 admin | Microsoft Learn, after you assign licenses to a group, you should check to make sure that the licenses were successfully assigned. The Groups tab on the License details page shows the status of the task for each group you assigned licenses to. You can use this page to find groups that have errors that must be resolved. For more information, see Find users with license errors in the group.
- In the admin center, go to the Billing > Licenses page, and select the product that you assigned the group to.
- On the Licenses details page, select the Groups tab. The Status column shows the license assignment status for each group. The following list describes the group statuses:
- All licenses assigned: The licenses were successfully assigned to every person in the group.
- In progress: The licenses are still being assigned to some members of the group.
- Errors & issues: There was an error in assigning licenses to at least one member of the group.
Please also note:
- Group-based licensing doesn't currently support nested groups (groups that contain other groups). If you assign licenses to a nested group, only users in the first-level group are assigned licenses.
- There are some limitations of group-based licensing in the Microsoft 365 admin center.
Additionally, you may also try to use audit logs to monitor group-based licensing activity.
For more information, please kindly refer to Resolve group license assignment problems - Microsoft Entra ID | Microsoft Learn.
Meanwhile, since we provide some limited knowledge about some aspects of Exchange on-premises related scenarios. We only expert support for pure Exchange online environment only. However, we have also a dedicated team with special expertise in Exchange Hybrid (Experts on both exchange on-premises and exchange online). Therefore, you can place your query on Microsoft Exchange Hybrid Management - Microsoft Q&A as well. I believe they will give you possible solution and information for your concern.
Appreciate your patience and understanding and thank you for your time and cooperation. I wish you all the best!