I recall having issues with license keys not being found on boot, back when first using WO 5.0.
WO was loading faster than the license software - so patching the Codemeter software resolved the problem for me.
Tom
As Neil said, patching Codemeter is what you need to do. This doesn't exactly 'fix' the issue in my experience, but a vast improvement.
You can download the patch from here:
http://www.wibu.com/en/downloads-user-software.html
Cheers,
Tom
Ensure that SP1 is installed for Windows, I had this issue and that along with an update to codemeter solved it.
Seems to me that SP1 shouldn't just be listed as a recommendation, but as a requirement for WO5.
Hope this solves your issue.