WDM unable to get device configuration, stays in-progress

I'm very new to WDS having just started looking into it and installing WDM 5.0 Workgroup this week. I'm wanting to use WDM to update Windows CE and reconfigure some S30 thin clients for a server change. I've been able to do everything I've tried so far except this one thing. When I try to right-click a device and Get Device Configuration, it goes through the wizard fine, but it stays in Scheduled Packages as In-Progress. Checking the folder with the name I gave it in the repository folder in Explorer, no file ever shows up. The scheduled item will fail if I reboot the thin client, but I've let it sit for quite a while and still get nothing.

So far for troubleshooting, I've disabled Windows firewall. Is there something else I'm missing?