Waiting a minute or so doesn't make a difference? I See this in later versions, but I've never questioned it, it initially doesn't see the activation but then it switches to activated after recognizing the user is logged in. I've never had to restart it to get it to work though.
Only thing I could think of is potentially the Software Protection Service is configured to a delayed or manual start where it should be automatic. Otherwise, I am not sure why there is a delay.
Do you mean the Software Protection Service on the image/virtual desktop?
Flip that to Auto or Auto Delayed. If it's manual, the service doesn't get started until an activation attempt happens when the app is launched, which might cause the delay. If it's running before the activation goes out, you should get the activation immediately.
So I set the service to Automatic start on the image and republished my desktops. I then logged into the new desktop but unfortunately, the service did not start even after waiting several minutes.
I then decided to start the service on the desktop and opened Word but it was still not activated until closing and reopening it.
Maybe it is not something I need to worry about it.