I use two commands to do this. I got them from somewhere, can't remember where right now. First is a VBscript that preforms the operation you can shange the "Pin to Start Menu" to "Pin to Taskbar" (same for "Unpin...": Set objShell = CreateObject("Shell.Application") set filesystem = CreateObject("scripting.Filesystemobject") Set objFolder = objShell.Namespace(filesystem.GetParentFolderName(Wscript.Arguments(0))) Set objFolderItem = objFolder.ParseName(filesystem.GetFileName(WScript.Arguments(0))) Set colVerbs = objFolderItem.Verbs For Each objVerb in colVerbs If Replace(objVerb.name, "&", "") = "Pin to Start Menu" Then objVerb.DoIt If Replace(objVerb.name, "&", "") = "Unpin from Start Menu" Then objVerb.DoIt Next Then I make a cmd file with the items I want to Pin and point them to the VBScript: cd /d %~dp0 WScript.exe %~dp0PinToStartMenu.vbs "path to app you want to Pin" You can add multiple Items in the cmd file to Pin/Unpin all the items you want.