Hello @JosephSia2,
Thank you for your question and for thoroughly documenting the steps you took. I followed your steps to reproduce the issue and got the same results, and I believe the issue may have been caused when the machine was restarted. When restarting the machine, it’s normally also necessary to also restart the Workflow Manager service. If that’s the case then restarting your Workflow Manager service may resolve this, as it did for me when testing.
Normally, restarting the machine shouldn’t be necessary when installing Workflow Manager. When authorizing ArcGIS Workflow Manager Server, ArcGIS Server should immediately recognize the updated licensing. If you have questions or run into issues feel free to post here again or consult the Installation and Deployment page of our documentation.
Best regards,
Robert Smith