Hi Jason,
The offline computer does not need internet access or a Microsoft account. You can complete the activation from a separate internet-connected device; the account used for the Product Activation Portal is not added to the server.
On Windows Server 2008 R2, open Command Prompt as administrator and run:
slmgr.vbs /ipk XXXXX-XXXXX-XXXXX-XXXXX-XXXXX
slmgr.vbs /dti
Enter the displayed Installation ID into the portal from another device. When it provides the Confirmation ID, return to the offline server and run:
slmgr.vbs /atp <Confirmation-ID>
slmgr.vbs /dlv
This requires a valid Retail or MAK key. If it is a KMS key, the server must connect to your organisation’s KMS host instead. If portal sign-in is prohibited entirely, contact Microsoft Volume Licensing Support; there is no longer an anonymous offline activation route.
Please also note that Windows Server 2008 R2 is out of support and should be upgraded where possible.
Thank you, and feel free to respond back for more assistance.