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Applying a custom theme to Windows Server 2012R2 RDP Sessions

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I have a Windows Server 2012R2 Terminal Services server with over 100 users logging on (not all at the same time).
There is a GPO that sets the theme to a custom theme file (that must be used), which is stored in a directory that all users have access to.

If I log into that server as a user via the VMware console, the theme applies.
I can then log on via RDP and theme is still there.

However, if that user has never logged on before and I log in via RDP, without first logging on via the console, the theme will NOT load.  Multiple logon attempts do not help.  I can log on via the console and any point and the theme will apply, but this is not practical for 100+ users.

The GPO obviously works, otherwise I wouldn't get the theme when logging on via the console.

Why would a theme work fine if logged on locally (or via console), but not via RDP?



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