The Dont set the always do this checkbox machine setting should be configured correctly. If this policy is enabled, the "Always do this..." checkbox in Autoplay dialog will not be set by default when the dialog is shown. Fix: (1) GPO: Computer Configuration\Administrative Templates\Windows Components\AutoPlay Policies\Don't set the always do this checkbox (2) KEY: HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\Policies\Explorer\DontSetAutoplayCheckbox