Hi Chris,
Hope you are doing good.
Please be informed that HASP HL License Manager (8.32.5.40) is not officially supported over Windows Server 2008 R2. In your case may be it is successfully installed but not allowing the sync between the key and the Aladdin Monitor.
Please confirm is the Application working under the scenario mentioned by you.
If not, you can try by uninstalling the lmsetup.exe completely from the system, restart the machine and install it again.
You can also try to install our latest Hasp drivers (not officially tested for your scenario) from the below path:
http://sentinelcustomer.safenet-inc.com/DownloadNotice.aspx?dID=8589947119
(Please remove lmsetup.exe first)
Thanks,
Heena