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Securing Windows Server 2008 R2 : DirectAccess

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10/20/2011 3:27:56 PM
Imagine if you could be anywhere on the planet, connected to the Internet and still have no hassle access to all of your corporate assets. I am sure many of you are thinking, “I already have that! I VPN in, and...”. Well, to be more specific, how about the same LAN style corporate access, but without the VPN hassle?

Well, with Windows 2008 R2, Microsoft released an amazing new feature called DirectAccess, and the name says it all. DirectAccess allows you and your users to gain access to the internal corporate resources in your environment from the Internet, without first connecting to a VPN, and without requiring user intervention to connect!

The benefit is apparent from a user’s perspective. They have access to corporate resources such as Web pages, file shares, and applications from any Internet-connected location. It is a secure connection and the user experiences mimics being directly connected to the corporate environment, thus giving the user a seamless experience between being in the office and out of the office.

The benefits that may not be as apparent are the advantages DirectAccess bring into play for the administrative team. Administrators can utilize DirectAccess technology to their advantage in a number of ways. One way DirectAccess lessens the burden of the help desk is by reducing the learning curve associated with VPN access. When users are in the office they have one way of accessing resources. Put them out on the Internet, and now they have to battle with VPN connections before their resource access returns. Account lockout problems can occur, issues around client VPN software must be addressed, and of course, users have to be taught to utilize the software as well.

By deploying DirectAccess connections into corporate resources, look and act the same for a user regardless if they are on the Internet or connected directly to the Intranet. The maintenance and management of VPN software and infrastructure is something that can be scaled down as its usage lessens. Additionally, the Windows 7 and Windows 2008 R2 native DirectAccess feature set leaves your users with little to nothing to learn, since the connection is seamless.

Another benefit that DirectAccess brings to administrators relates to system maintenance. In most corporate environments, mobile users are a wild card. Since they only connect to the environment intermittently, keeping them patched and up to date with the latest policies can be tricky.

Normally, an administrator must rely on a user to either VPN into the corporate network or actually walk into a company facility and connect to the LAN. This can make the time between updates unpredictable and it can leave users’ machines in a vulnerable state. By being able to access a user’s machine whenever they are connected to the Internet, the story changes dramatically.

With DirectAccess, the user merely has to connect to the Internet from anywhere in the world. Once on the Internet, their computer will automatically connect to the corporate network, authenticate, and give them access to network resources while at the same time giving your network maintenance tools the ability to connect to them. By being able to patch and manage policies on machines that normally might not connect into the network for long durations at a time, you can be that much more efficient at keeping your corporate systems up to date. In the next sections, we will explore DirectAccess in more detail to see how you can choose to utilize it to secure and also enable your mobile user workforce.

DirectAccess infrastructure requirements

In order to deploy DirectAccess, you will need to take into consideration the infrastructure dependencies that exist with DirectAccess. The first key thing to be aware of with DirectAccess is that both IPv6 and IPsec play a critical role in the deployment. Regardless of the deployment model chosen, users on the Internet will only be able to gain access to servers on the Intranet capable of running IPv6.

IPSec is the protocol of choice in routing traffic securing across the Internet; however, once a client has connected into the DirectAccess servers and been granted Intranet access, IPSec encryption becomes an option within the LAN. It is recommended to continue IPSec within the internal network, but ultimately, it is the administrator’s choice by design. Regardless of whether IPsec is in use, only the IPv6-capable servers on the Intranet will be accessible by DirectAccess users.

Other DirectAccess infrastructure requirements include:

  • Active Directory Domain Services

  • Group Policy

  • At least one Windows 2008 Domain Controller

  • DNS services that support DNS message exchanges over Intrasite Automatic Tunnel Addressing Protocol (ISATAP)

  • A PKI infrastructure for IPSec certificate issuance

DirectAccess protocols

Multiple protocols are in use when a client is utilizing DirectAccess. At times, the connection circumstances will dictate which protocol is to be utilized, while at other times, the architecture design will indicate which protocol is more appropriate. The following protocols may be utilized as a part of DirectAccess encapsulation technology:

  • Intra-Site Automatic Tunnel Addressing Protocol —A transition technology that provides for IPv6 unicast communications between IPv4/IPv6 hosts across an IPv4-only Intranet.

  • 6to4 —Provides for unicast communications between IPv4/IPv6 hosts and IPv6-capable sites across the Internet

  • Teredo —Provides for unicast communication between NAT’ed IPv4/IPv6 hosts across the Internet to IPv6 capable sites

  • IP-HTTPS —Tunnels IPv6 within an HTTP over SSL connection, allowing for connectivity even while in restricted sites.

  • IPSec —Tunnels IPv6 across IPv4 networks.

If a client connected to the Internet has been assigned a publically routable IP address, they will utilize the 6to4 protocol to attempt connection into the DirectAccess architecture. If the client is behind a NAT, then they will instead utilize the Teredo protocol to connect. If the client cannot use either 6to4 or Teredo, it will then attempt to connect with IP-HTTPS. However, something to keep in mind is that IP-HTTPS is a slower technology, and there is the potential impact on client performance.

Selecting a DirectAccess model

Before jumping headlong into a DirectAccess deployment, the first step an administrator must take is to determine the DirectAccess model they would like to employ. The level of security required across organizations will vary in stringency, and administrators have the choice to build a design that maps to the organization’s specific security needs. Microsoft defines three DirectAccess models that can be evaluated to determine the architecture that is a best fit for your environment. The three main access models that we will discuss are:

  • Full Intranet Access

  • Selected Server Access

  • End-to-End Access

In some environments, the thought of allowing access to internal protected company resources from the Internet seems daunting, while in others, the accessibility is readily welcomed. Regardless of the security stance of your organization, you can build a secure access model to meet your business need. All three of the access models follow some of the same security principles and contain the same infrastructure elements. Let us review the high-level similarities across the three access models first.

The first commonality is: to ensure that data transference is secure when traversing the Internet, DirectAccess utilizes a two-step IPsec Encapsulating Security Payload (ESP) tunnel to connect. The first connection made by the client regardless of the access model will always be an infrastructure tunnel. The Infrastructure tunnel enforces computer authentication.

Full Intranet Access

This deployment model is the most similar to what exists today in many companies with VPN solutions deployed. In the traditional VPN model, the user makes an initial connection to a server on the perimeter, and once authenticated, is typically able to browse the internal network without restriction. With DirectAccess configured in the Full Intranet Access model, the scenario is similar.

The first step in connection is always the infrastructure tunnel. Once the infrastructure tunnel is complete, the user will authenticate and establish an intranet tunnel. The intranet tunnel users both computer and user-based authentication and it is used to connect to the DirectAccess server on the perimeter. Once the intranet tunnel has been established to the DirectAccess server, the client can browse and access LAN-based resources as if they were directly connected.

The DirectAccess server is functioning as an IPSec gateway and all IPSec traffic from the Internet terminates at the DirectAccess server. Transmissions from the client to the internal applications are still sent with the IPv6 protocol, but without the IPSec encryption that was present from the client to the DirectAccess server. The DirectAccess server continues to encrypt and decrypt IPSec traffic between the client and the Intranet resources.

For environments with Windows 2003-based resources in the LAN, this is the best deployment model. Since Windows 2003 servers do support the use of IPv6, but not IPSec with IPv6, they will only be accessible while the DirectAccess server is functioning as an IPSec gateway. Any resources that are not able to support IPv6 will not be accessible without the deployment of a third-party translator and DNS gateway.

Full Intranet Access with Smart Card Authentication

The Full Intranet Access with Smart Card Authentication model represents the same architecture as the Full intranet Access model, just with the addition of Smart Cards for an additional layer of user authentication protection. The DirectAccess server can be configured to enforce the user of Smart Cards on the Intranet tunnel before allowing user access to resources.

Selected Server Access

If your organization requires more selective access to internal resources for external clients, then this is the deployment model for you. By utilizing the Selected Server Access model, you enforce that client to utilize the IPSec Encapsulating Security Payload (ESP). It enables peer-to-peer authentication utilizing computer credentials and allows the clients to validate the identity of the server they are connecting to. This way the clients can determine if IPSec is required to connect to specific services on the Intranet.

In environments that contain the services of a sensitive nature, this model allows you to single out specific targets for Intranet-based IPSec encryption while traffic to other services on the Intranet remains clear. All traffic to and from the Internet is still secured by the IPsec gateway services provided by the DirectAccess servers.

End-to-End Access

In the End-to-End Access model, resources on the Intranet are made accessible to Internet users directly. End-to-End Access enforces IPsec from the DirectAccess client and the Intranet resource in a point-to-point fashion. IPSec peer authenticate using computer credentials should be configured and ESP is recommended.

Overall, in this model, the DirectAccess servers get a break. Since all tunneling is performed directly between the client on the Internet and the resource on the Intranet, much of the overhead is offloaded onto the endpoints instead of relying on the DirectAccess server for translation. The DirectAccess server simply performs pass-through for the IPSec traffic and does not function as a gateway in this model.

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