18.9.59.3.9.3 (L1) Ensure 'Require use of specific security layer for remote (RDP) connections' is set to 'Enabled: SSL'

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Information

This policy setting specifies whether to require the use of a specific security layer to secure communications between clients and RD Session Host servers during Remote Desktop Protocol (RDP) connections.
The recommended state for this setting is: Enabled: SSL.
Note: In spite of this setting being labelled SSL, it is actually enforcing Transport Layer Security (TLS) version 1.0, not the older (and less secure) SSL protocol.

Rationale:
The native Remote Desktop Protocol (RDP) encryption is now considered a weak protocol, so enforcing the use of stronger Transport Layer Security (TLS) encryption for all RDP communications between clients and RD Session Host servers is preferred.

Solution

To establish the recommended configuration via GP, set the following UI path to Enabled: SSL:
Computer Configuration\Policies\Administrative Templates\Windows Components\Remote Desktop Services\Remote Desktop Session Host\Security\Require use of specific security layer for remote (RDP) connections
Note: This Group Policy path is provided by the Group Policy template TerminalServer.admx/adml that is included with all versions of the Microsoft Windows Administrative Templates.

Impact:
TLS 1.0 will be required to authenticate to the RD Session Host server. If TLS is not supported, the connection fails.
Note: By default, this setting will use a self-signed certificate for RDP connections. If your organization has established the use of a Public Key Infrastructure (PKI) for SSL/TLS encryption, then we recommend that you also configure the Server authentication certificate template setting to instruct RDP to use a certificate from your PKI instead of a self-signed one. Note that the certificate template used for this purpose must have ?Client Authentication? configured as an Intended Purpose. Note also that a valid, non-expired certificate using the specified template must already be installed on the workstation for it to work.
Note #2: Some third party two-factor authentication solutions (e.g. RSA Authentication Agent) can be negatively affected by this setting, as the SSL/TLS security layer will expect the user's Windows password upon initial connection attempt (before the RDP logon screen), and once successfully authenticated, pass the credential along to that Windows session on the RDP host (to complete the login). If a two-factor agent is present and expecting a different credential at the RDP logon screen, this initial connection may result in a failed logon attempt, and also effectively cause a ?double logon? requirement for each and every new RDP session.

Default Value:
Negotiate. (The most secure method that is supported by the client is enforced. If TLS is supported, it is used to authenticate the RD Session Host server. If TLS is not supported, native RDP encryption is used, but the RD Session Host server is not authenticated.)

References:
1. CCE-33025-8

See Also

https://workbench.cisecurity.org/files/2754