The Always prompt for password upon connection machine setting should be configured correctly. Specifies whether Remote Desktop Services always prompts the client for a password upon connection. You can use this setting to enforce a password prompt for users logging on to Remote Desktop Services, even if they already provided the password in the Remote Desktop Connection client. By default, Remote Desktop Services allows users to automatically log on by entering a password in the Remote Desktop Connection client. If the status is set to Enabled, users cannot automatically log on to Remote Desktop Services by supplying their passwords in the Remote Desktop Connection client. They are prompted for a password to log on. If the status is set to Disabled, users can always log on to Remote Desktop Services automatically by supplying their passwords in the Remote Desktop Connection client. If the status is set to Not Configured, automatic logon is not specified at the Group Policy level. However, an administrator can still enforce password prompting by using the Remote Desktop Session Host Configuration tool. Fix: (1) GPO: Computer Configuration\Administrative Templates\Windows Components\Remote Desktop Services\Remote Desktop Session Host\Security\Always prompt for password upon connection (2) KEY: HKLM\SOFTWARE\Policies\Microsoft\Windows NT\Terminal Services\fPromptForPassword