Group Policy Failing to Apply

[toxicandy]

With windows server 2003 losing support in the coming weeks we have upgraded our 2003 servers to virtualized 2008 servers. The only problem we are having at the moment is with Group Policy and mapping drives. Previous to this upgrade we used a logon.vbs which "worked" but was nearing 10 years old and did have faults every once in a while. However since the change the script is a complete bust, broken, no drives map from it and so we have to run to each work station and remap drives manually. We have since removed the logon.vbs from being used and replayed it with the Drive Maps under User Configuration->preferences->Windows Settings. We are using replace with these drives and also Item level targeting to target the security group for different people. We have in total about 20-25 drives however we have some repeated drives (three instances of S:) but they are all to totally different groups that would not coincide with each other. So they should never have to be mapped onto the same computer, this still isn't the problem. Currently (Day 8) we have had 2 computers no grab any of the drives they were supposed to, both users were in the groups, we ran a gpupdate /force followed by a restart and still nothing, I then ran a gpresult /h and couldn't find anything as to why it would fail. DNS checked out fine and no one had any complications there. We also had 2 other computers that grabbed 4-5 drives correctly but missed one. Is there any big reason that sticks out in anyone’s mind why this is happening?

EDIT

Ran a Report from GPM on one of the computers and it came back with this under the drive maps:

Group Policy Drive Maps: Failed
Group Policy Drive Maps failed due to the error listed below.
The system cannot find the path specified.
Additional information may have been logged. Review the Policy Events tab in the console or the application event log for events between 5/28/2015 8:39:31 AM and 5/28/2015 8:39:31 AM.

All paths are correct and the same policy works on a number of computers. When on their computer I am able to type the exact path mapped VIA the drive maps and it comes up perfectly fine.

[CimmerianX]

Did you map them before by IP, DNS name, or netbios name? Did you replicate the method exactly.

Off the top of my head you could have 2 issues here.
1) The method used to map the drive is not setup on the workstation. i.e. \server.here.local\share doesn't map because the workstation is using wrong dns, maybe an invalid hosts file entry.
2) Server load... if you have 100 PCs each mapping mulitple drives all at the same time of the morning (logon time), perhaps the guest os or host os is under load

[toxicandy]

I think I may have something. We still have 2 windows 2003 servers to be moved over however 1 does have GPM on it and when we run
GPRESULT /R
The server that group policy was applied from changes between 3-4 servers which all have GPM on it. All the servers replicate GPM from the same server (we'll call it Server a)

So

Server A is our primary Domain Controller

Server B will replicate any changes made to GPM on Server A over so they are the same on Server B
Server C and Server D do the same as Server B.

But I did say that one was Server 2003 and as far as I know drive map doesn't work on Windows server 2003 correct? You have to use Logon.vbs instead? As I said in my main post, we disabed Logon.vbs and it replicated, as I just checked, across to all the other servers. So if someone used the server with 2003 on it when they logged in is it possible that policy was not applied but if they were lucky and it used one of the other servers where the drive map works that it applied smoothly and worked no problem?