Hello Matthew Decarlo,
Thank you for reaching out to Microsoft!!
To reactivate your subscription, below steps might help resolve the issue
- Go to the Microsoft 365 Admin center - sign in with your administrator account.
- Navigate to the Billing section - click on billing from the sidebar
- Locate the expired subscription - Find the E5 subscription that expired.
- Reactivate the subscription - Click on "Reactivate" next to the subscription. If you don't see this option, you might need to contact Microsoft support for further assistance.
If reactivation is not possible, you can create a new tenant and start creating a new subscription.
Please find the below referenced links for possible workaround:
Link: Reactivate your subscription
Link: Renewal of Expired Microsoft 365 E5
Hope this helps.
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