I've been trying to set up roaming profiles and folder redirection, but have hit a bit of a snag with the latter. This is exactly what I've done so far:

(I have OU permissions and GPO permissions over my division's OU.)

1. Created a group called Roaming-Users in the OU 'Groups'
2. Added a single user (testuser) to the group
3. Using the Group Policy Management tool (via RSAT on Windows 7) I right-clicked on the Groups OU and selected 'Create a GPO in this domain, and Link it here'
4. Added my 'Roaming-Users' group to the Security Filtering section of the policy.
5. Added the Folder Redirection option, specifically for Documents. It is set to redirect to: \myserver\Homes$\%USERNAME%\Documents (Homes$ exists and is sharing-enabled).
6. Right-clicked on the policy under the Groups OU and checked Enforced.
7. Logged into a machine as testuser successfully. Created a simple text file, saved some gibberish, logged off.
8. Remoted into the server with Homes$ on it, noticed that the directory Homes$\testuser was created, but was empty. No text file to be found.

From what I've read, I did everything I aught to...but I can't quite figure out the issue. I had no errors when I logged off about syncing issues (offline files is enabled) or anything, so I can only imagine my file should have ended up up on the share.

Any ideas?

EDIT: Using gpresult /R, I confirmed the user is in fact part of the Roaming-Users group, but does not have the policy applied, if that helps.

EDIT 2: Apparently you can't apply GPOs to groups...so I applied to users and used the same security filter to limit it to my test user. Nothing happens as far as redirection goes, but I now have the following error in the event log:

Folder redirection policy application has been delayed until the next logon because the group policy logon optimization is in effect