If Windows update is not working it is usually because the pages are being cached by the WinGate server, you can solve this problem by creating a policy in WinGate to not cache the update pages.

To create a caching policy to not cache MS Update pages:

1. Go to the system tab in GateKeeper and double click caching
2. Select What to cache and change the radio button to specify which requests will be cached
3. Click Add Filter, click Add Criterion
4. Choose This criterion is NOT met if
5. HTTP URL
6. contains
7. windowsupdate
8. Click ok, ok

Now any pages with windowsupdate in the URL will not be cached and your Windows updates should work.