Here are a few examples of how to pin items to the Classic Shell Start Menu using Group Policy Preferences and as always navigate to here inside of Group Policy Management:
User Configuration > Preferences > Windows Settings > Shortcuts
Right-click Shortcuts > New > Shortcut
To add the Windows Calculator to the Start Menu…
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Classic Shell is a necessary evil for any normal Windows user who wants to be able remain productive with introduction of the Start Screen in Server 2012 and Windows 8. As a network administrator, I highly recommend Classic Shell because it even has it’s own Group Policy templates that you can add in with the PolicyDefinitions inside your domain’s SYSVOL folder so you can at least somewhat try to put the Start Menu back to the way it once was. The Start Screen is a technical support person’s worst nightmare for novice users who don’t deal well with change (and trust me they don’t).
If you’re trying to customize a Remote Desktop Server environment, one somewhat annoying thing you will run into is trying to get rid of the first run wizard for Classic Shell. Obviously, the first run wizard is handy for anybody who wants to customize the look and feel of their Start Menu, but more than likely in a Remote Desktop environment, you’re going to want all this predefined with no user interaction so the chances of them screwing things up is slim to none.
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