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Windows Server

Windows Server 2008 : Configuring IP Security (IPsec)

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11/27/2010 5:54:11 PM
The IP Security (IPsec) protocol is a standard that provides cryptographic security services for IP traffic. IPsec is an end-to-end security solution. The only two nodes aware of IPsec traffic on the network are the two peers communicating with each other. IPsec packets are forwarded by routers like any other packet on the network. As you probably recall, IPsec provides the following properties:
  • Peer authentication. IPsec verifies the identity of a peer computer before data is sent.

  • Data origin authentication. Each IPsec packet has an encrypted checksum in the form of a keyed hash. It ensures that only one computer could have sent the packet, preventing a malicious user from masquerading as the sender.

  • Data integrity. The IPsec protocol protects the contents of the packet through the encrypted checksum. The receiver of the data can verify the data is unmodified by checking the checksum value. A malicious intruder would be unable to properly modify both the packet’s data and it cryptographic checksum.

  • Data confidentiality. IPsec uses secret key encryption techniques that protect the data being sent in the packet. If the packet is intercepted, only the packet’s encrypted contents can be viewed.

  • Anitreplay. Each protected packet has a sequence number that prevents an intruder from getting in the middle of the communications and modifying packet data.

  • Key management. IPsec provides a secure way of deriving initial keying data and to periodically change the keys used for secure communications to prevent the key from being discovered through any other method than brute force.

IPsec does not provide nonrepudiation security service for data, meaning that the sender can later deny having sent the packet. IPsec uses a shared secret key, called a symmetric key, and since two peers share a key, nonrepudiation is not provided by IPsec.

IPsec can operate in either transport mode or tunnel mode. The transport mode protects communications between hosts and it encrypts the User Datagram Protocol/Transmission Control Protocol (UDP/TCP) protocol header and original data but not the IP header itself. In tunnel mode, IPsec protects host-to-network communications like that in virtual private networks (VPN). Since IPsec changes the IP packet, the original version of Network Address Translation did not support IPsec. However, the newer version, Network Address Translation–Traversal (NAT–T) is used. It allows IPsec traffic to pass through NAT–T compatible servers that are configured to allow traffic on UDP port 4500. All versions of Windows that support IPsec also support NAT–T.

IPsec supports numerous authentication and encryption standards, so two IPsec-capable computers might not support the same sets of standards. And, not all computers can support IPsec. So, before an IPsec connection can be made, whether in transport or tunnel mode, an IPsec negotiation is established to determine if the IPsec supported by the two end points (host-to-host or host-to-server) are supporting the same standards.

IPsec provides security by enveloping the data (the IP payload) in an additional header or trailer that provides data origin authentication, data integrity, data confidentiality, and antireplay protection. The IPsec protocol uses two elements, the authentication header (AH) and the encapsulating security payload (ESP) header and trailer. Applying the AH or ESP to an IP datagram transforms the packet into a secure datagram. As a result, AH and ESP sometimes are referred to as transforms. ESP is widely supported and is therefore the preferred IPsec protocol, but AH is the fallback protocol if both hosts cannot support ESP. Let’s look briefly at the AH and ESP protocols.

IPsec Authentication Header (AH)

The Authentication Header protocol provides data origin authentication, data integrity, and antireplay protection for the entire IP datagram. It does not provide data confidentiality (for that, use ESP, discussed in the next section). AH can be used in transport or tunnel mode. The packet format for both is shown in Figure 1. Notice that when AH is used in transport mode (Figure 10.19A), the AH header is added just after the IP header. The IP header is modified to indicate the presence of AH (the Protocol field is set to 51). This packet type is forwarded by routers just as any other standard IP packet would be. However, firewalls look for the modification of the IP header and might not allow this traffic through due to the modification of the Protocol field in the IP header. For that reason, some firewalls might need to be configured to forward data in which the IP header Protocol field is set to 51.

Figure 1. AH in Transport and Tunnel Mode


In Figure 10.19B, the tunnel mode for AH is shown. In this case, the IP packet is included without modification and the entire packet is authenticated, including the new IP header, the AH header, and the original IP header and payload. This added header allows the packet to pass through firewalls more easily but it does generate more network traffic by adding to the packet size.

Head of the Class ...: IPsec Headers and Footers

A security association (SA) is the combination of security services used by communicating peers. This typically includes security services, protection methods, and cryptographic keys. The SA contains the information needed to negotiate a secure communications between peers. Two types of SAs are created when IPsec peers communicate in a secure mode: ISAKMP SA and IPsec SA.

The Internet Security Association and Key Management Protocol (ISAKMP) SA also is known as the main mode SA and is used to protect IPsec security negotiations themselves. The IPsec SA also is known as the quick mode security association (SA). The IPsec SA cipher information is protected by the ISAKMP SA. In IPsec packets, no information about the type of traffic or the protection mechanisms is sent as plaintext. Recall that for a pair of IPsec peers, there are always two IPsec SAs—one for inbound and one for outbound traffic. The inbound SA for one IPsec peer is the outbound SA for the other IPsec peer.


IPsec Encapsulating Security Payload (ESP)

Encapsulating Security Payload (ESP) provides both a header and a trailer for an IP datagram that secures the packet. ESP provides data origin authentication, data integrity, antireplay, and data confidentiality protection for the ESP-encapsulated portion of the packet. Figure 2 shows the format of the ESP header in transport mode and Figure 3 shows the ESP header in tunnel mode. We’ve also included what the packet looks like if you use both AH and ESP, shown in Figure 2, though typically ESP is used as the default method of security the packet unless you have reason to use AH, which does not provide data confidentiality.

Figure 2. ESP in Transport Mode


Figure 3. ESP in Tunnel Mode


Figure 4. AH and ESP Packet Format


Now that we’ve refreshed your skills on the format of the IPsec AH and ESP data, let’s get back to the practical IPsec skills needed to configure a Windows Server 2008 computer network.

Configuring IPsec in Windows Server 2008

IPsec is configured via Group Policy in Active Directory as well as through Windows Firewall with Advanced Security. In Windows Firewall with Advanced Security, IPsec inbound and outbound traffic rules can be configured along with connection security rules. In this section, we’ll look briefly at IPsec in Group Policy and then we’ll take a more detailed look at the integration of IPsec in Windows Firewall with Advanced Security since this is a new feature in Windows Server 2008.

In Windows Server 2003, configuring IPsec and configuring the Windows Firewall were configured separately and in two different places. This led to the possibility of conflicting settings. In Windows Server 2008, IPsec and the Windows Firewall functionality have been combined, removing the possibility of conflicting settings. IPsec and Windows Firewall are now configured via the Windows Firewall with Advanced Security snap-in. Note that the command line options, within the netsh advfirewall context, can be used for command line configuration of both firewall and IPsec behavior. Again, the command line options are helpful when setting up scripting, batch files, or when administering a remote server—so it’s useful to make note of the commands you’re most likely to need. You’ll also see some of the more commonly used command line commands on the Windows Server 2008 exam, so we’re including them when it seems likely you’ll see it on the exam.

New & Noteworthy...: IPsec in Windows Server 2008

There are many new improvements to the IPsec implementation in Windows Server 2008. According to the Microsoft Web site, these are:

  • Integrated firewall and IPsec configuration

  • Simplified IPsec policy configuration

  • Client-to-DC IPsec protection

  • Improved load balancing and clustering server support

  • Improved IPsec authentication

  • New cryptographic support

  • Integration with Network Access Protection

  • Additional configuration options for protected communication

  • Integrated IPv4 and IPv6 support

  • Extended events and performance monitor counters

  • Network Diagnostics Framework support

[Source: http://technet.microsoft.com/en-us/library/bb726965.aspx]

In the Window Server 2008 exam, expect to see questions that test your knowledge and understanding of the latest implementation of IPsec. Most notably, be familiar with how IPsec is integrated into and configured in the firewall. Also be aware of the Simplified IPsec policy configuration, which will likely show up on your exam in one form or another. Finally, be familiar with the integrated IPsec support with IPv4 and IPv6. Refer to the Microsoft Web site if you need to dig into the vast detail of IPsec in Windows Server 2008.


Creating IPsec Policy

IPsec policy is created either in Active Directory as a Group Policy or via the Windows Server 2008’s Windows Firewall with Advanced Security. Clearly, IPsec settings in these two areas are related but are not interchangeable. Policy set in Active Directory is applied according to policies set at the domain level and will take precedence over local IPsec policy located on a member computer. IPsec policy will be applied according to AD and Windows Firewall with Advanced Security settings on a Windows Server 2008 computer.

We won’t go into too much detail about AD IPsec policy here but we will discuss IPsec in Windows Firewall with Advanced Security in more detail later in this chapter. You can open the IP Security Policy Management console through the MMC snap-in. To open the MMC Console, click Start | Run and type mmc, then click OK. This opens the MMC console from which you can select the IPSecurity Management Snap-in. Right-click IP Security Policies in the left pane then choose Create IP Security Policy from the menu to launch the IPsec Security Policy Wizard.

IPsec Using the Command Line

As with many other functions in Windows Server 2008 management, you can configure IPsec policy via the command line. This section briefly outlines some of the more commonly used IPsec commands. However, you may want to explore the command line options for IPsec on your own so you’re familiar with these options. You can configure static mode and dynamic mode options, as shown in Table 1. You can type netsh ipsec /? to get a full list of command line options related to IPsec.

Table 1. IPsec Command Line Options
IPsec CommandDetails
netsh ipsec static add policy nameCreates an IPsec policy with the specified name.
netsh ipsec static delete [option]Deletes the specific IPsec policy. Can be used with the switch all to remove all IPsec policies, filter lists, and filter actions.
netsh ipsec dynamic set policy nameSets a policy name immediately.
netsh ipsec dynamic delete nameRemoves a specific policy immediately.
netsh ipsec dynamic export policy nameExports all IPsec policies to a specified file.
netsh ipsec dynamic show allUsed to view IPsec policy and statistics.
netsh ipsec dynamic set config ipsecdiagnostics 7Enables IPsec driver logging of dropped inbound and outbound packets.
netsh ipsec dynamic set config ipsecloginterval 60Used to change the default interval the IPsec log file writes entries to the log file. This example sets the interval to 60 seconds. This can be helpful in troubleshooting IPsec issues/.

Head of the Class ...: Saving Command Line Output to a File

Sometimes the output of a command line command, such as a “show all” command, can be quite lengthy and can scroll off the screen making it hard to locate needed information. You can save the output to a file by using this sequence of commands. Although the example is used for the netsh ipsec context, this works anywhere in the command line context.

At the netsh command line context, type set filename filename.txt (where filename.txt is the file you want to create). Then, type ipsec static show all. Finally, type set file close. The contents of the ipsec static show all command have been saved to the filename you specified.

Even faster is the command from the standard command line context (not within netsh): netsh ipsec static show all > filename.txt. Saves time, saves your data.

If you want to see the entire output without dumping it to a file, you can use the |more switch so the command would be netsh ipsec static show all |more.


IPsec Isolation Policy

Server and domain isolation is accomplished through configuring IPsec computers to require protection for inbound traffic (or attempts at inbound traffic) and to request but not require protection for outbound traffic. Trusted computers in an isolation scenario use fallback to clear to initiate communication with hosts on their intranets that are not IPsec-enabled. However, beginning in Windows Server 2003 (and continued in Windows Server 2008), the Simple Policy Update changes the IPsec negotiation process. IPsec negotiation failures will still fallback to clear but because negotiation falls back to clear, it’s possible for two peers using IPsec who cannot validate each others’ credentials to allow unsecured communication with non-IPsec aware computers (if this setting is enabled) or to accept unsecured communication but always respond using IPsec (if the setting is enabled).


Other -----------------
- Windows Server 2008 : Configuring Network Authentication (part 2)
- Windows Server 2008 : Configuring Network Authentication (part 1)
- Windows Server 2008 : Configuring IPv4 and IPv6 Addressing
- Windows Server 2008 : Managing the Terminal Services - Displaying Data Prioritization
- Windows Server 2008 : Managing the Terminal Services - Viewing Processes & Monitoring Sessions
- Windows Server 2008 : Managing the Terminal Services - Limits
- Windows Server : Managing the Terminal Services - RDP Permissions
- Windows Server : Configuring TS Remote Desktop Web Connection
- Windows Server : Configuring TS Web Access
- Windows Server : Configuring TS RemoteApp
- Windows Server 2003 : The Terminal Services Gateway (part 2)
- Windows Server 2003 : The Terminal Services Gateway (part 1)
- Windows Server 2008 : Disaster Scenario Troubleshooting
- Windows Server 2008 : Recovering from a Disaster - When Disasters Strike
- Windows Server 2008 : Ongoing Backup and Recovery Preparedness
- Windows Server 2003 : Restoring Active Directory
- Windows Server 2003 : Backing Up Active Directory
- Windows Server 2003 : Managing Schema Modifications
- Windows Server 2008 : Perform a Full Server Recovery of a Domain Controller by Using the Command Line
- Windows Server 2008 : Perform a Full Server Recovery of a Domain Controller by Using the Windows Interface
 
 
 
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