If the “Reconnect at logon” option is selected, a network drive that is mapped to a Web share is displayed as a red X after you restart a computer that is running Windows Vista or Windows Server 2008
On a computer that is running Windows Vista or Windows Server 2008, you map a network drive to a Web share, and then you select the Reconnect at logon option. Then, you restart the computer, or you log off and then log back on again. In this situation, the mapped drive is displayed as a red X. Additionally, you may receive the following error message:
Could not reconnect all network drives
Additionally, when you double-click to the mapped drive to access it, you may receive the following error message:
An error occurred while reconnecting Drive: to https://localhost/share
Web Client Network: The operation being requested was not performed because the user has not been authenticated.
This connection has not been restored.
When this problem occurs, you have to disconnect and then remap the Web share.
This problem may occur if the Web share requires certificate-based Secure Sockets Layer (SSL) authentication.
For more information on this issue, including potential causes, workarounds, and resolutions, see: Microsoft KB Article KB960646.