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VPN in Windows Server 2008 R2

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3/20/2011 11:25:37 AM
A virtual private network (VPN) is the extension of a private network that encompasses links across shared or public networks like the Internet. A VPN allows data to be sent between two computers across the Internet in a manner that emulates a point-to-point private link. With a virtual private network, illustrated in Figure 1, a private link is created between the client and the VPN server by encrypting the data for confidentiality; data packets that are intercepted while traveling through the Internet are unreadable without the proper encryption keys.
Figure 1. Virtual private networking across the Internet.


VPN technology provides corporations with a scalable and low-cost solution for remote access to corporate resources, such as database, file, and directory servers. VPN connections allow remote users to securely connect to their corporate networks across the Internet. Remote users would access resources as if they were physically connected to the corporate local area network (LAN).

Note

A new technology introduced with Windows Server 2008 R2 called DirectAccess is discussed. Microsoft has positioned DirectAccess as being different from a traditional VPN. This positioning is based mainly on the automated nature of DirectAccess, rather than on technical or architectural differences. DirectAccess is technically a VPN.


Windows Server 2008 R2 RRAS Features and Services

Windows Server 2008 R2 builds on the Routing and Remote Access features that were provided by Windows NT 4.0, Windows 2000 Server, Windows Server 2003, and Windows Server 2008. Routing and Remote Access in Windows Server 2008 R2 includes all of the VPN features and services from previous versions of the Windows Server product and adds several key features.

The following VPN features were provided by Windows NT 4.0:

  • IP packet filtering

  • Point-to-Point Tunneling Protocol (PPTP) support for router-to-router VPN connections

  • Routing and Remote Access administrative tool and the Routemon command-line utility

The following additional VPN features were provided by Windows 2000 Server:

  • Layer 2 Tunneling Protocol (L2TP) over Internet Protocol Security (IPSec) support for router-to-router VPN connections and remote access.

  • Demand-dial routing that can route IP and Internetwork Packet Exchange (IPX) over on-demand or persistent wide area network (WAN) links, such as analog phone lines, Integrated Services Digital Network (ISDN), or over VPN connections that use either PPTP or L2TP over IPSec.

  • RRAS integration that provides the capability to integrate a firewall with RRAS and Network Address Translation (NAT) functions.

Windows Server 2003 continued the evolution of RRAS by adding some new features. Some of the Routing and Remote Access Service for Windows Server 2003 features included the following:

  • Quarantine Policy Check.

  • Improved administration and management tools that use a Microsoft Management Console (MMC) snap-in or the Netsh command-line tool.

Windows Server 2008 added new VPN functionality and improved on some of the existing functionality. The features new in Windows Server 2008 included the following:

  • Network Policy Server (NPS) to provide access control and to assess, validate, and remediate the health of clients; this replaces the Windows Server 2003 Quarantine Policy Check.

  • Secure Socket Tunneling Protocol (SSTP) to provide for HTTPS VPN tunnels over port 443 to seamlessly provide connectivity over firewalls, NAT, and web proxies.

  • Point-to-Point Protocol (PPP), which now supports the use of Protected EAP (PEAP) with PEAP-MS-CHAP v2 and PEAP-TLS for better security.

  • Full IPv6 support in addition to IPv4 support, both of which coexist completely.

  • New Connection Manager Administration Kit (CMAK) features, such as multiple language support.

  • Connection Manager, which now supports Dynamic DNS client registration.

  • Network Diagnostics Framework Client-based connections to support basic diagnostics capabilities with the Network Diagnostics Framework.

  • New cryptographic L2TP/IPSec-based VPN connections, which now support the Advanced Encryption Standard (AES) with 128- and 256-bit keys.

  • Windows Server 2008 R2 shows evolutionary progress in the area of remote access.

  • VPN Reconnect enables users to transparently reconnect to traditional VPN connections even when roaming or changing networks, which is made possible through the implementation the IKEv2 mobility function, MOBIKE.

Components Needed to Create a Traditional VPN Connection

A point-to-point link, or tunnel, is created by encapsulating or wrapping the data with a header that provides routing information that allows the data to travel through the Internet. A virtual private network connection requires a VPN client and a VPN server or infrastructure. A secured connection is created between the client and server through encryption that establishes the tunnel, as shown in Figure 2.

Figure 2. Establishing a VPN tunnel between a client and server.


The tunnel is the portion of the connection in which data is encapsulated. The VPN connection is the portion of the connection where the data is encrypted. The data encapsulation, along with the encryption, provides a secure VPN connection.

Note

A tunnel that is created without the encryption is not a VPN connection because the private data is sent across the Internet unencrypted and can be easily read. This violates the “P” for Private in a Virtual Private Network (VPN).


The figure also depicts the roles in a typical Windows 2008 VPN infrastructure. The roles in Windows Server 2008 R2 consist of the following:

These roles work together to provide the VPN functionality.

A shared or public internetwork is required to establish a VPN connection. For Windows Server 2008 R2, the transit internetwork is always an IP-based network that includes the Internet as well as a corporation’s private IP-based intranet.

The VPN Client

A VPN client is a computer that initiates a VPN connection to a VPN server. Microsoft clients, including Windows NT 4.0, Windows 9x, Windows 2000, Windows XP, Windows Vista, and Windows 7, can create a remote access VPN connection to a Windows Server 2008 R2 system.

VPN clients can also be any non-Microsoft PPTP client or L2TP client using IPSec.

The RRAS Server

An RRAS server is a Windows Server 2008 R2 server with the Network Policy and Access Services role installed and the Routing and Remote Access Service role services installed. This is the server that accepts VPN connections from VPN clients. The RRAS server name or IP address must be resolvable as well as accessible through corporate firewalls, which could be by either having a network interface connected to the demilitarized zone (DMZ) or by providing the appropriate access rule on the firewall.

The NPS System

The Network Policy Server (NPS) provides the authentication, authorization, auditing, and accounting for the VPN clients. The NPS system has the Network Policy and Access Services role installed with the Network Policy Server role service installed. In Windows Server 2008, NPS was an English-only solution. In Windows Server 2008 R2, support is added for non-English character sets.

The Network Policy Server (NPS) is used to enforce network access policies for client health, client authentication, and client authorization. NPS works with Network Access Protection (NAP), which is a technology to manage, enforce, and remediate client health. The NPS service provides the policies for NAP to validate against. NPS also has multiple templates for larger-scale deployments or configuring multiple NPS servers identically.

In NAP, System Health Agents (SHAs) are used to inspect and assess the health of clients according to policies. System Health Validators (SHVs) are the policies that the agents validate against.

The Windows Security Health Agent is the SHA in Windows 7 and the Windows Security Health Validator is the SHA in Windows Server 2008 R2. These provide the following features in their SHVs:

  • Firewall software installed and enabled

  • Antivirus software installed and running

  • Current antivirus updates installed

  • Antispyware installed and running

  • Current antispyware updates installed

  • Microsoft Update Service enabled

These are configured in the client health policies or SHVs on the NPS. When a client attempts a connection, the client SHA will send a Statement of Health (SoH) to the NPS system. The SoH is compared with the health policy, resulting in a pass or a fail. Based on that result, the NPS does one of four actions. In the case of a pass (that is, the client is healthy), it just allows the client to connect. In the case where the SoH fails the policy comparison (that is, the client is unhealthy), the NPS can prevent the client from connecting, connect the client to a restricted network, or even allow the client to connect even though it is unhealthy, as shown in Table 1.

Table 1. NPS Actions
SoH Versus PolicyNPS Action
PassesClient is allowed to connect.
FailsClient is not allowed to connect; client is connected to a restricted network; or client is allowed to connect even if it is deemed unhealthy.

When a client fails and is not allowed to connect, that is straightforward. When the client fails and is connected to a restricted network, this allows the client to connect to secured remediation servers to download software, patches, and/or updates to be remediated. The SHA can even conduct remediation automatically and then allow the client to connect. Interestingly, in some cases, the client might fail and yet the policy still allows it to connect. This might be for reporting purposes.

Additionally, third-party SHVs and SHAs can be written that access the NAP application programming interface (API).

Remediation server groups can be configured to restrict noncompliant VPN clients to just those servers where software and updates are stored. After the appropriate software and updates are applied that bring the client into compliance, the NPS will allow the clients full access to the network.

This server handles VPN client authentication requests for the RRAS server and validates those requests against its policies. This allows for a centralized policy and access control, while allowing the RRAS server role to be scaled out as needed.

Certificate Server

The certificate server is a Certificate Authority (CA) that issues certificates for the servers and clients to use in the authentication and encryption of tunnels. In Windows Server 2008 R2, this is a Windows Server 2008 R2 server with the Active Directory Certificate Services role installed with the Certification Authority and the Certification Authority Web Enrollment role services installed. These roles also require some other supporting roles to be installed, such as the Web Server (IIS) role and the File Services role.

Using Windows Server 2008 R2 allows the administrator to issue and control certificates for the VPN infrastructure. This could also be handled by a third-party CA such as VeriSign, thereby not requiring a server albeit at an annual cost.

Although not a requirement for all configurations of the VPN infrastructure, certificates are considered a best practice to enhance the security of the VPN infrastructure. An AD certificate server is always required for DirectAccess deployment.


Active Directory Server

The Active Directory server provides the authentication database for the VPN client users. In Windows Server 2008 R2, this is a server with the Active Directory Domain Services role installed.

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