When booting up your computer, the Pogoplug Application may generate a warning that it is disconnected, and the warning disappears when you click Retry. This issue only occurs when:
The Pogoplug Application is installed.
Pogoplug Preferences -> Start on login is checked.
Here is the technical problem: the Pogoplug Application currently does not have a way to tell Windows to load the drive before it loads the drive application. When the drive application loads first, it is calling on a component that is not yet running and interprets this to mean that the service is not up and running. The Pogoplug Application does not have a way to distinguish between an actual service outage and problem like this.
The best solution is simply to uncheck the Start on login option in Pogoplug Preferences.