Windows 7/8 update will not initially check wsus

Question

I have a weird (probably simple) problem. I recently updated a Windows 8 image file for our organization, and while everything works fine with deployment, Windows update is giving us some issues. When we go to run WU after an image, we only have the option to "check online for updates from windows update." This is different from the behavior in the past, since we have a WSUS server and manage all of our updates from there. The normal option for us is the link that reads "check for updates managed by your system administrator."

The weird part is that when you click the link, only the first time mind you, to look on windows update, 100% of the time it fails with error code 80244019. Again, this only happens the first time, when the client machine is trying to connect to windows update. The second attempt always works and windows receives its updates from WU, then gives us an option to check for our managed updates.

So, Here's the desired behavior we would like: Computer images, tech goes to WU, tech clicks on "check for updates managed by your system administrator" updates run. I am using SCCM to inject updates into our images monthly anyways, so we don't really need the client machines to call out to Microsoft-land. Does anyone have any ideas why this is happening, or how to fix it?