This assumes you have the "Squeezebox server tray tool" in your Startup folder. From the Windows start button you can type "customize icons" in the search box. In the list presented you should then be able to select "Customize icons on the Taskbar". This will bring up the control panel that handles notification area icons on the Taskbar. You have a couple of choices here, you can check the box at the bottom to "Always show all icons and notifications on the taskbar" or scroll to the "Squeezebox Server Tray Icon" in the list of notification area icons and select "Show icons and notifications".
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