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Windows Server

Windows Server 2008 : Deploying Terminal Services Gateway

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10/29/2010 6:47:42 PM

Overview of Terminal Services Gateway

TS Gateway is an optional TS component that enables authorized Remote Desktop clients to establish Remote Desktop Protocol (RDP) sessions between the Internet and Terminal Services resources found behind a firewall on a private network. (“Terminal Services resources,” in this case, refers both to terminal servers and to computers with Remote Desktop enabled.) As they pass over the Internet, RDP connections to a TS Gateway server are secured and encrypted by the Secure Sockets Layer (SSL) protocol. A key feature of TS Gateway is that it enables RDP traffic to stream through corporate firewalls at TCP port 443, which is normally open for SSL traffic. (By default, RDP traffic communicates over TCP port 3389.)

In a basic TS Gateway deployment, shown in Figure 1, a user on a home computer (point 1) connects over the Internet to TS Gateway (point 2) located behind an external corporate firewall.

Figure 1. Basic TS Gateway scenario


The connection from points 1 to 2 is established by means of the RDP protocol encapsulated in an HTTPS (HTTP over SSL) tunnel. To receive this HTTPS connection in the perimeter network, the TS Gateway server must be running the Internet Information Services (IIS) Web server. After receiving the connection, the TS Gateway server then strips away the HTTPS data and forwards the RDP packets to the destination terminal servers (point 3) located behind a second, internal firewall. In this scenario, if incoming connections are allowed or denied to Active Directory accounts, Active Directory Domain Services must be installed on the TS Gateway.

As an alternative to the basic scenario illustrated in Figure 1, you can use Internet Security and Acceleration (ISA) Server instead of a TS Gateway server to serve as the SSL/HTTPS endpoint for the incoming TS client connection. In this scenario, illustrated in Figure 2, ISA Server (point 2) serves as either an HTTPS-to-HTTPS or an HTTPS-to-HTTP bridge to the TS Gateway server (point 3), and the TS Gateway server then directs the RDP connection to the appropriate internal resource (point 4). This method provides the advantage of protecting Active Directory information within the corporate network.

Figure 2. TS Gateway with ISA Server used for SSL termination




Installing and Configuring a TS Gateway Server

You can install and configure a TS Gateway server first by adding the TS Gateway role service and then by configuring the clients to point to the TS Gateway server. These steps are described in detail in the following section.

Adding the TS Gateway Role Service

When you choose to add the TS Gateway role service by using Server Manager, the Add Role Services Wizard launches. The Add Role Services Wizard then performs two main tasks. First, it automatically installs (if necessary) the prerequisite role services for TS Gateway: the IIS Web server and Network Policy Server (NPS). Second, it guides you through the process of configuring the three component features of TS Gateway that are required for the role service to function: a server certificate for SSL encryption, a TS Connection Authorization Policy (TS CAP), and a TS Resource Authorization Policy (TS RAP).

  • Server Certificate for SSL TS clients connections to TS Gateway are encrypted by using SSL (also known as Transport Layer Security [TLS]), which requires a server certificate. This server certificate can originate from a trusted third-party certificate authority (CA) or from a trusted local CA (such as Certificate Services). As a less secure alternative suitable for testing environments, the Add Role Services Wizard can also generate a self-signed server certificate for use with TS Gateway.

    Important: The client must trust the server’s root certificate

    Every TS client that connects to the TS Gateway server must trust the CA that issued the TS Gateway server’s certificate. If neither a trusted third-party CA nor a CA integrated in the client’s own Active Directory domain has issued the certificate, you must export and install TS Gateway Server Root Certificate in the Trusted Root Certification Authorities store on the Terminal Services client. You can view this store by using the Certificates snap-in. For a demonstration of this procedure, see the practice section at the end of this lesson.


    Figure 3 shows the page in the wizard on which you can specify or create a server certificate for SSL encryption.

    Figure 3. Choosing a server certificate for SSL encryption

  • TS CAP A TS CAP essentially is a policy that specifies which external users or computers can connect to TS Gateway. The Add Role Services Wizard enables you only to create the first and primary TS CAP, but you can create others later by using the administrative console for TS Gateway, TS Gateway Manager.

    Note: TS Gateway Manager and TS CAPs

    To open TS Gateway Manager, click Start, point to Administrative Tools, point to Terminal Services, and then click TS Gateway Manager.

    To create a new TS CAP in TS Gateway Manager, right-click the Connection Authorization Policies folder in the console tree, select Create New Policy in the shortcut menu, and then point to Wizard or Custom, as desired. To modify the properties of an existing TS CAP, right-click an existing TS CAP in the Connection Authorization Policies pane, and then click Properties.


    On the Select User Groups That Can Connect Through TS Gateway page of the Add Role Services Wizard, the process of creating the first TS CAP is simplified and enables you to specify users (typically, Active Directory security groups) that are permitted to connect. These same user groups are then made available to the main TS RAP created next by the wizard.

    Note that a TS CAP also enables you to choose an authentication method for remote users: Password, Smart Card, or both.

    The Select User Groups page is shown in Figure 4.

    Figure 4. Defining groups for a TS CAP and TS RAP

    When you use the TS Gateway Manager console to create or modify a TS CAP, you also have the option of specifying the computers for which you want to enable access to TS Gateway. Another configuration choice for a TS CAP, available only in the TS Gateway Manager console, is the option to restrict device redirection. In other words, you can use a TS CAP to prevent certain client devices such as a USB drive from being redirected to the TS user session through TS Gateway.

    The properties sheet of a TS CAP, available in the TS Gateway Manager console, is shown in Figure 5.

    Figure 5. Modifying a TS CAP

  • TS RAP A TS RAP is a TS Gateway policy that specifies which users can connect to which Terminal Services resources in an organization. The Add Role Services Wizard enables you to create the first and primary TS RAP, but you can create others later by using the TS Gateway Manager console.

    Note: TS Gateway Manager and TS RAPs

    To create a new TS RAP in TS Gateway Manager, right-click the Resource Authorization Policies folder in the console tree, select Create New Policy in the shortcut menu, and then click Wizard or Custom, as desired. To modify the properties of an existing TS RAP, simply right-click an existing TS RAP in the Resource Authorization Policies pane, and then click Properties.


    In the simplified policy created by the Add Role Services Wizard, you determine whether the user group you have selected on the Select User Groups That Can Connect Through TS Gateway page should be granted access to all terminal servers on the network or merely a subset, defined by an Active Directory security group.

    The Create A TS RAP For TS Gateway page of the Add Role Services Wizard is shown in Figure 6.

    Figure 6. Creating a TS RAP in the Add Role Services Wizard

    As with a TS CAP, using the TS Gateway Manager console to create or modify a TS RAP presents additional configuration options. For example, when you use the TS Gateway Manager console to create a TS RAP, the computer group to which you enable access can be an Active Directory security group or a TS Gateway-managed computer group, as shown in Figure 7. This latter group type is used only for TS Gateway and is created only through the TS Gateway Manager console. A second TS RAP configuration choice only available in the TS Gateway Manager console is the option to control the TCP ports through which a TS client may connect to a resource. For example, you can restrict all RDP connections to TCP port 3389 (the standard port for RDP), or you can specify a nonstandard port or set of ports on which the computer group will listen for connections.

    Figure 7. Specifying a computer group for an RAP



Configuring Remote Desktop Connection to Use TS Gateway

To use Remote Desktop Connection to initiate connections through TS Gateway, you must first configure RDC to use the gateway. To do so, first open RDC, click the Options button if necessary, and then select the Advanced tab. On the Advanced tab, click the Settings button in the Connect From Anywhere section, as shown in Figure 8.

Figure 8. Configuring RDC to use TS Gateway, step 1


This procedure opens the Gateway Server Settings dialog box, as shown in Figure 9.

Figure 9. Configuring RDC to use TS Gateway, step 2


In the Gateway Server Settings dialog box, select the Use These TS Gateway Server Settings option. Then, specify the TS Gateway server in the Server Name box and an appropriate logon method (password or smart card) in the Logon Method box. To force RDC to use TS Gateway even for computers on your LAN, clear the option to bypass TS Gateway for local addresses.

In the Logon Settings area of the dialog box, you can specify whether the TS Gateway server should pass your credentials along to the target terminal server. By default, this option is selected. However, if you need to enter a different username or password at the remote server, clear this option.

Other -----------------
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- Windows Server 2008 : Configuring Terminal Services (part 3)
- Windows Server 2008 : Configuring Terminal Services (part 2)
- Windows Server 2008 : Configuring Terminal Services (part 1)
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- Windows Server 2008 : Configuring Server Storage (part 1)
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