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Copying a file to a user directory using a group policy on Windows Server 2003 with Win 10 clients fails

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I have a network of around 100 Windows XP boxes, plus a number of Windows 10 ones, in a Windows Server 2003-hosted Active Directory. There's a tender in process to replace both the clients and the server with current hardware and server software, but until that happens I'm stuck with the shortcomings of this server platform.

In any case my task is to make sure that upon login of a domain user, a specific file is copied from the server to his/her directory. This is trivial task if the server is 2008 or later, but for 2003 it isn't.

For that purpose, I've first uploaded the file to be distributed to a network-accessible share, accessible as //UNC_full_path/file.

I then created a GPO (with computer-options disabled) and configured the user section to contain a single startup script. The script file was named (for the sake of completeness) copyfile.cmd and was placed in the section offered by the GPO (\domainname.local\SYSVOL\domainname.local\Policies{policyid}\User\Scripts|logon). The contents of the file was the following command:

IF NOT EXIST "%USERPROFILE%\file" copy \\UNC_full_path\file "%USERPROFILE%"

I finally removed Authenticated users as the target of the policy and added only domain admins, to make some test runs.

On Windows XP after a gpupdate /force /boot and logging as the administrator, everything works as planned: the file is copied to the user directory, if it does not exist. If it exists, nothing happens, as planned.

Making a test run on Windows 7 was also succesful. However, performing the same feat on Windows 10 does not produce anything at all... In fact, Windows 10 clients seem to be "stubborn", disrespecting all GPOs that utilize some sort of cmd-based commands scripts, as I've tested.

I'm clueless as to how I can proceed to troubleshoot this issue. Any ideas will be welcome.

Again, please do remember we are talking Server 2003, so the usual 2008+ tricks do not apply.


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