I have a full video of all the possible scenarios when using iLok Cloud here
iLOK CLOUD | IN DEPTH
https://youtu.be/NKZINYC7W_0
Since the video they have introduces a couple new features called Automatic Mode and Managed Mode which you can read about here
https://ilok-com.s3.amazonaws.com/iLokCloud.pdf
Keep in mind, not all iLok licenses are cloud enabled.