Unfortunately this is not so much an issue with GaiaUpgrade, but an issue with Gaia. We have not been able to identify why Gaia thinks the user is not logged in. GaiaUpgrade makes the requests to Gaia, using the same requests that Gaia uses, but the response Gaia returns is the log in issue sometimes. We will continue looking into this to hopefully resolve it. I apologize for the inconvenience.