After some research I was surprised to find how complex some processes are.  I wanted a simple Group Policy to deploy fonts and found that the most straight forward way to deploy fonts via GPO was to build an .MSI and then deploy the .MSI.  This sounds harder than it is:

Building the .MSI for the Fonts

1 – Get the Registry Settings

1. Manually Install the fonts in question on your own PC (because it is much easier to copy the registry entries than it is to type them 🙂 )
2. Launch RegEdit and expand to HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Fonts
3. Click FILE > EXPORT and save the file as some name you like
4. Open the resulting .REG file with Notepad and remove all references to other fonts

2 – Use the Freeware Version of Advanced Installer to Build and .MSI

1. Download and install the freeware version of Advanced Installer then start it
2. Select NEW > INSTALLER > scroll down in the right window and select SIMPLE, then click the CREATE PROJECT button
3. Enter a PRODUCT NAME and a COMPANY NAME if you wish
4. Scroll down and select the DISABLE MODIFY check box – this is not required but might confuse users if it is left on
5. From the left menu select INSTALL PARAMTERS and select the LIMIT TO BASIC USER INTERFACE checkbox
6. From the left menu select FILES AND FOLDERS and expand TARGET COMPUTER > WINDOWS VOLUME > WINDOWS > FONTS
7. From the top menu select FILES and select the fonts files
8. From the left menu select REGISTRY and expand TARGET COMPUTER >HKEY_LOCAL_MACHINE > SOFTWARE > MICROSOFT > WINDOWS NT > CURRENT VERSION > FONTS
9. From the top menu select IMPORT REG and point to the REG file you created in the GET REGISTRY SETTINGS section above
10. From the top menu select FILE > SAVE AS and name your project what you like
11. From the top menu select HOME tab, select BUILD and name your .MSI what you like

3 – Deploy Your Fonts Using Group Policy

1. Copy the .MSI from step 11 above to a place on the network that all computers have access
2. On your Windows Server, open your GROUP POLICY MANAGEMENT CONSOLE
3. Expand the OU containing the COMPUTERS (not Users) you want to install the fonts on
4. Right click and select CREATE NEW GPO then name it as you wish
5. Right click on that GPO and select EDIT
6. Expand COMPUTER CONFIGURATION > POLICIES SOFTWARE SETTINGS
7. Right click on SOFTWARE INSTALLATION and select NEW > PACKAGE
8. Point to the .MSI that contains your fonts and make doubly sure that you are using a UNC path (no drive letters!) and that all the PC’s can see that path.
9. Wait for GPO to be applied (or run a GPUPDATE /FORCE if you can’t wait)
10. Reboot
11. have a nice day!

Much of these instructions were inspired by THIS article which is older but contains screen shots of the Advanced Installer tool that you might find handy.