GPO not applying at logon

What would make a GPO fail to be applied at logon, but work when you run gpupdate?
I've applied a policy to add a desktop shortcut to a group of thin clients. All changes are lost on reboot, so it's easy to test whether this is being applied or not. If the machine is left alone long enough, the policy will be applied. I know this because all the machines that have been up and running for days have the shortcut. But when I reboot one of them it's not there.
If I run gpupdate, it appears.
There is another policy linked to the same OU that maps a couple of drives and it is applied as soon as Windows is up. It was created by someone else.
Am I doing something wrong here? Why don't my policies apply at logon but others do?
I've applied a policy to add a desktop shortcut to a group of thin clients. All changes are lost on reboot, so it's easy to test whether this is being applied or not. If the machine is left alone long enough, the policy will be applied. I know this because all the machines that have been up and running for days have the shortcut. But when I reboot one of them it's not there.
If I run gpupdate, it appears.
There is another policy linked to the same OU that maps a couple of drives and it is applied as soon as Windows is up. It was created by someone else.
Am I doing something wrong here? Why don't my policies apply at logon but others do?
CISSP | CCNA:R&S/Security | MCSA 2003 | A+ S+ | VCP6-DTM | CCA-V CCP-V
Comments
In the meantime, what if you put a batch file in the startup folder to run gpupdate?
Does the GPO apply a script the put the shortcut there? Where is the script located?
The clients are actually VMs that are sitting out there running until the Citrix provisioning server hands them to the user, so they do have network connections.
There isn't any script - just a desktop shortcut added via GPO
Since these thin clients are running off cookie cutter VMs that are provisioned through Citrix, anything I do has to be via GPO. It's not a mission critical shortcut, so they'll survive the way it is for now, but I do need to fix it somehow.
If this script that is setting up the shortcut is on a network share then that is most likely your issue. When rebooting the computer is not getting the network connection setup quick enough to run this script on a network share. Try delaying it till after a connection has been established.
The GPO that is applying successfully at logon (the mapped drives created by someone else) is actually running via a script on the SYSVOL - so I think I should be ok there.
The specific line you need from there is
Group Policy core (UserEnv) and registry CSE
%windir%\debug\usermode\UserEnv.log
UserEnvDebugLevel = REG_DWORD 30002
HKEY_LOCAL_MACHINE\Software\Microsoft\Windows NT\CurrentVersion\Winlogon
This has helped me track down a good number of nefarious GPO problems. You may also want to try turning on:
Computer Configuration\Administrative Templates\System\Logon\ Always wait for the network at computer startup and logon
To read more about it look here: Group Policy Processing
Yeah, it should. Sorry I misread part of the question.
This might help and fix the issue possibly. Not 100% sure but something to try.
MCITP: EA, VA, SA
VCAP-DCD, VCP6 -- COMING SOON
I tried the "wait for network" option that a couple of people suggested and it solved half my problem - Woot! The certificate is now installed by the time I check after logon.
The desktop shortcut still doesn't apply, so I'm researching that here and there. One notable difference is that the certificate was a computer policy and the shortcut is a user preference. Not sure if that changes the direction of any thought patterns. I may end up using a gpupdate script for now - just bugs me. Thanks for all the replies/suggestions!
Enabling Group Policy Preferences Debug Logging using the RSAT - Ask the Directory Services Team - Site Home - TechNet Blogs