Due to some legal issues that have never been explained the DisplayLink drivers won’t install on Windows Server. Here is how I managed to install the drivers (I got the from this site):
- Installed the 5.1.20177 drivers with Windows 2000 compatibility mode.
- Attached my USB monitor and it installed, but the tray icon utility had an error about incompatible video drivers.
- Extracted the 5.2.21675 drivers with 7-Zip.
- Navigated to the USB Video card in the device manager and chose to update the driver with the 5.2.21675 drivers.
Notes: I haven’t tried if two USB monitors works with this method. The tray icon utility is not being displayed, but the monitor has worked fine so far. I originally tried updating with a 5.3xxx driver but the tray icon utility crashed and upon rebooting the USB video device couldn’t start because the driver wasn’t signed.