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Chapter 9
IP Security
“If a secret piece of news is divulged by a spy before the time is ripe, he
must be put to death, together with the man to whom the secret was told.”
—The Art of War, Sun Tzu
objectives
• Present an overview of IP security (IPsec).
• Understand the concept of security association.
• Explain the difference between transport mode and tunnel
mode.
• Discuss the alternatives for combining security
associations.
• Present an overview of Internet Key Exchange.
IP Security Overview
• RFC 1636
• “Security in the Internet Architecture”
• Issued in 1994 by the Internet Architecture Board (IAB)
• Identifies key areas for security mechanisms
• Need to secure the network infrastructure from unauthorized
monitoring and control of network traffic
• Need to secure end-user-to-end-user traffic using authentication
and encryption mechanisms

• IAB included authentication and encryption as necessary
security features in the next generation IP (IPv6)
• The IPsec specification now exists as a set of Internet standards
• IPsec provides the
capability to secure
communications
across a LAN, private
and public WANs,
and the Internet
• Principal feature of
IPsec is that it can
encrypt and/or
authenticate all traffic
at the IP level
• Thus all distributed
applications
(remote logon,
client/server, email, file transfer,
Web access) can
be secured
Applications of IPsec
Examples of IPsec applications include:
• Secure branch office connectivity over the Internet: A company can build a
secure virtual private network over the Internet or over a public WAN. This
enables a business to rely heavily on the Internet and reduce its need for private
networks, saving costs and network management overhead.
• Secure remote access over the Internet: An end user whose system is equipped
with IP security protocols can make a local call to an Internet Service Provider
(ISP) and gain secure access to a company network. This reduces the cost of
toll charges for traveling employees and telecommuters.
• Establishing extranet and intranet connectivity with partners: IPsec can be
used to secure communication with other organizations, ensuring
authentication and confidentiality and providing a key exchange mechanism.
• Enhancing electronic commerce security: Even though some Web and
electronic commerce applications have built-in security protocols, the use of
IPsec enhances that security. IPsec guarantees that all traffic designated by the
network administrator is both encrypted and authenticated, adding an
additional layer of security to whatever is provided at the application layer.
Benefits of IPSec
• Some of the benefits of IPsec:
• When IPsec is implemented in a firewall or router, it provides strong
security that can be applied to all traffic crossing the perimeter
• Traffic within a company or workgroup does not incur the overhead of securityrelated processing

• IPsec in a firewall is resistant to bypass if all traffic from the outside must
use IP and the firewall is the only means of entrance from the Internet into
the organization
• IPsec is below the transport layer (TCP, UDP) and so is transparent to
applications
• There is no need to change software on a user or server system when IPsec is
implemented in the firewall or router

• IPsec can be transparent to end users
• There is no need to train users on security mechanisms, issue keying material on a
per-user basis, or revoke keying material when users leave the organization

• IPsec can provide security for individual users if needed
• This is useful for offsite workers and for setting up a secure virtual
subnetwork within an organization for sensitive applications
Routing
Applications
• IPsec can play a vital role in the routing architecture required
for internetworking

IPsec can assure that:
A router
advertisement comes
from an authorized
router

A router seeking to
establish or maintain
a neighbor
relationship with a
router in another
routing domain is an
authorized router

A redirect message
comes from the
router to which the
initial IP packet was
sent

A routing update is
not forged
Confidentiality

Encapsulating Security
Payload (ESP)
• Consists of an encapsulating
header and trailer used to
provide encryption or
combined
encryption/authentication
• The current specification is
RFC 4303, IP Encapsulating
Security Payload (ESP)

Internet Key Exchange (IKE)
• A collection of documents
describing the key management
schemes for use with IPsec
• The main specification is RFC
5996, Internet Key Exchange
(IKEv2) Protocol, but there are a
number of related RFCs

Key
Management

Authentication
Authentication Header (AH)
• An extension header to
provide message
authentication
• The current specification is
RFC 4302, IP Authentication
Header

Architecture
• Covers the general concepts,
security requirements,
definitions, and mechanisms
defining IPsec technology
• The current specification is
RFC4301, Security Architecture
for the Internet Protocol

IPsec
Documents

Cryptographic algorithms
• This category encompasses
a large set of documents
that define and describe
cryptographic algorithms for
encryption, message
authentication,
pseudorandom functions
(PRFs), and cryptographic
key exchange

Other
• There are a variety of
other IPsec-related RFCs,
including those dealing
with security policy and
management information
base (MIB) content
IPsec Services
• IPsec provides security services at the IP layer by enabling a system
to:
• Select required security protocols
• Determine the algorithm(s) to use for the service(s)
• Put in place any cryptographic keys required to provide the requested
services

• RFC 4301 lists the following services:
•
•
•
•
•
•

Access control
Connectionless integrity
Data origin authentication
Rejection of replayed packets (a form of partial sequence integrity)
Confidentiality (encryption)
Limited traffic flow confidentiality
IPSec Services
Authentication
Header

Encapsulating Security Payload
Security Association
(SA)
• A one-way logical connection
between a sender and a receiver
that affords security services to
the traffic carried on it
• In any IP packet, the SA is
uniquely identified by the
Destination Address in the
IPv4 or IPv6 header and the
SPI in the enclosed extension
header (AH or ESP)

Uniquely identified by three parameters:

Security Parameters
Index (SPI)
• A 32-bit unsigned integer
assigned to this SA and
having local significance only

Security protocol
identifier
• Indicates whether the
association is an AH or
ESP security
association

IP Destination
Address
• Address of the
destination endpoint of
the SA, which may be
an end-user system or a
network system such as
a firewall or router
Transport and
Tunnel Modes
Transport Mode
• Provides protection primarily for
upper-layer protocols
• Examples include a TCP or UDP
segment or an ICMP packet
• Typically used for end-to-end
communication between two hosts
• ESP in transport mode encrypts
and optionally authenticates the IP
payload but not the IP header
• AH in transport mode authenticates
the IP payload and selected
portions of the IP header

Both AH and ESP support two
modes of use: transport and tunnel
mode.

Tunnel Mode
• Provides protection to the entire IP
packet
• Used when one or both ends of a
security association (SA) are a security
gateway
• A number of hosts on networks behind
firewalls may engage in secure
communications without implementing
IPsec
• ESP in tunnel mode encrypts and
optionally authenticates the entire inner
IP packet, including the inner IP header
• AH in tunnel mode authenticates the
entire inner IP packet and selected
portions of the outer IP header
Transport
and Tunnel
Mode
Protocols
Tunnel Mode and Transport Mode
Functionality
Authentication header
(ah)
• Provides support for data integrity and authentication (MAC
code) of IP packets.
• Guards against replay attacks.
Before Applying AH
Transport Mode (AH Authentication)

Tunnel Mode (AH Authentication)
Encapsulating security
payload (ESP)
• ESP provides confidentiality services.

• Encryption:
•
•
•
•
•
•

Three-key triple DES
RC5
IDEA
Three-key triple IDEA
CAST
Blowfish

• Authentication:
• HMAC-MD5-96
• HMAC-SHA-1-96
Transport Mode (ESP Encryption & Authentication)

Tunnel Mode (ESP Encryption & Authentication)
End-to-end vs end-to-intermediate
authentication
Transport Mode SA

Transport Mode SA
Tunnel Mode SA
Combining Security
Associations
• An individual SA can implement either the AH or ESP protocol but not both
• Security association bundle
• Refers to a sequence of SAs through which traffic must be processed to provide
a desired set of IPsec services
• The SAs in a bundle may terminate at different endpoints or at the same
endpoint
• May be combined into bundles in two ways:

Transport
adjacency

• Refers to applying more than one security protocol to the
same IP packet without invoking tunneling
• This approach allows for only one level of combination

Iterated
tunneling

• Refers to the application of multiple layers of security
protocols effected through IP tunneling
• This approach allows for multiple levels of nesting
Combining Security
Associations
Possible combinations:
a) AH in transport
mode.
b) ESP in transport
mode.
c) ESP followed by AH
in transport mode.
(ESP SA inside AH
SA)
d) Any a,b or c inside
AH or ESP in tunnel
mode.
Combining Security
Associations
• Security is provided
only between
gateways (routers,
firewalls, etc.) and
no hosts implement
IPsec.
• Simple VPN support
• Tunnel could
support AH, ESP or
ESP with
authentication
option
Combining Security
Associations
•
•

•

•

Combination of case 1 and
case 2
The gateway-to-gateway
tunnel provides either
authentication,
confidentiality, or both for all
traffic between end systems.
When gateway-to-gateway
tunnel is ESP, it also provides
limited form of traffic
confidentiality.
Individual hosts can
implement any additional
IPsec services required for
given applications or given
users by means of end-to-end
SAs.
Combining Security
Associations
• Combination of case
1 and case 2
• Provides support for
a remote host that
uses the Internet to
reach an
organization’s
firewall and then to
gain access to some
server or
workstation behind
the firewall.
• Only tunnel mode is
required between the
remote host and the
firewall.
Internet Key Exchange
The IPsec Architecture document mandates
• The key management
support for two types of key management:
portion of IPsec
• A system administrator
involves the
manually configures each
determination and
system with its own keys and
distribution of secret with the keys of other
communicating systems
keys
• This is practical for small,
• A typical
requirement is four
keys for
communication
between two
applications
• Transmit and
receive pairs for
both integrity and
confidentiality

relatively static environments

Manual

Automated
• Enables the on-demand
creation of keys for SAs and
facilitates the use of keys in a
large distributed system with
an evolving configuration
ISAKMP/Oakley
• The default automated key management protocol of IPsec

• Consists of:
• Oakley Key Determination Protocol
• A key exchange protocol based on the Diffie-Hellman algorithm but
providing added security
• Generic in that it does not dictate specific formats

• Internet Security Association and Key Management Protocol
(ISAKMP)
• Provides a framework for Internet key management and provides the
specific protocol support, including formats, for negotiation of
security attributes
• Consists of a set of message types that enable the use of a variety of
key exchange algorithms
ISAKMP/Oakley
• ISAKMP does not dictate a specific key exchange algorithm;
rather ISAKMP consists of a set of message types that enable
the use of a variety of key exchange algorithms.
• Oakley is the specific key exchange algorithm mandated for
use with the initial version of ISAKMP.

• Three authentication methods can be used with Oakley:
• Digital signatures
• Public-key encryption
• Symmetric-key encryption
Summary
• IP security overview
•
•
•
•
•
•
•

Applications of IPsec
Benefits of IPsec
Routing applications
IPsec documents
IPsec services
Security associations
Transport and tunnel
modes
• Authentication Header
(AH)
• Encapsulating Security
Payload (ESP)

• Combining security
associations
• Authentication plus
confidentiality
• Basic combinations of
security associations

• Internet key exchange
• ISAKMP/Oakley
• IKE Formats

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BAIT1103 Chapter 6

  • 1. Chapter 9 IP Security “If a secret piece of news is divulged by a spy before the time is ripe, he must be put to death, together with the man to whom the secret was told.” —The Art of War, Sun Tzu
  • 2. objectives • Present an overview of IP security (IPsec). • Understand the concept of security association. • Explain the difference between transport mode and tunnel mode. • Discuss the alternatives for combining security associations. • Present an overview of Internet Key Exchange.
  • 3. IP Security Overview • RFC 1636 • “Security in the Internet Architecture” • Issued in 1994 by the Internet Architecture Board (IAB) • Identifies key areas for security mechanisms • Need to secure the network infrastructure from unauthorized monitoring and control of network traffic • Need to secure end-user-to-end-user traffic using authentication and encryption mechanisms • IAB included authentication and encryption as necessary security features in the next generation IP (IPv6) • The IPsec specification now exists as a set of Internet standards
  • 4. • IPsec provides the capability to secure communications across a LAN, private and public WANs, and the Internet • Principal feature of IPsec is that it can encrypt and/or authenticate all traffic at the IP level • Thus all distributed applications (remote logon, client/server, email, file transfer, Web access) can be secured
  • 5. Applications of IPsec Examples of IPsec applications include: • Secure branch office connectivity over the Internet: A company can build a secure virtual private network over the Internet or over a public WAN. This enables a business to rely heavily on the Internet and reduce its need for private networks, saving costs and network management overhead. • Secure remote access over the Internet: An end user whose system is equipped with IP security protocols can make a local call to an Internet Service Provider (ISP) and gain secure access to a company network. This reduces the cost of toll charges for traveling employees and telecommuters. • Establishing extranet and intranet connectivity with partners: IPsec can be used to secure communication with other organizations, ensuring authentication and confidentiality and providing a key exchange mechanism. • Enhancing electronic commerce security: Even though some Web and electronic commerce applications have built-in security protocols, the use of IPsec enhances that security. IPsec guarantees that all traffic designated by the network administrator is both encrypted and authenticated, adding an additional layer of security to whatever is provided at the application layer.
  • 6. Benefits of IPSec • Some of the benefits of IPsec: • When IPsec is implemented in a firewall or router, it provides strong security that can be applied to all traffic crossing the perimeter • Traffic within a company or workgroup does not incur the overhead of securityrelated processing • IPsec in a firewall is resistant to bypass if all traffic from the outside must use IP and the firewall is the only means of entrance from the Internet into the organization • IPsec is below the transport layer (TCP, UDP) and so is transparent to applications • There is no need to change software on a user or server system when IPsec is implemented in the firewall or router • IPsec can be transparent to end users • There is no need to train users on security mechanisms, issue keying material on a per-user basis, or revoke keying material when users leave the organization • IPsec can provide security for individual users if needed • This is useful for offsite workers and for setting up a secure virtual subnetwork within an organization for sensitive applications
  • 7. Routing Applications • IPsec can play a vital role in the routing architecture required for internetworking IPsec can assure that: A router advertisement comes from an authorized router A router seeking to establish or maintain a neighbor relationship with a router in another routing domain is an authorized router A redirect message comes from the router to which the initial IP packet was sent A routing update is not forged
  • 8. Confidentiality Encapsulating Security Payload (ESP) • Consists of an encapsulating header and trailer used to provide encryption or combined encryption/authentication • The current specification is RFC 4303, IP Encapsulating Security Payload (ESP) Internet Key Exchange (IKE) • A collection of documents describing the key management schemes for use with IPsec • The main specification is RFC 5996, Internet Key Exchange (IKEv2) Protocol, but there are a number of related RFCs Key Management Authentication Authentication Header (AH) • An extension header to provide message authentication • The current specification is RFC 4302, IP Authentication Header Architecture • Covers the general concepts, security requirements, definitions, and mechanisms defining IPsec technology • The current specification is RFC4301, Security Architecture for the Internet Protocol IPsec Documents Cryptographic algorithms • This category encompasses a large set of documents that define and describe cryptographic algorithms for encryption, message authentication, pseudorandom functions (PRFs), and cryptographic key exchange Other • There are a variety of other IPsec-related RFCs, including those dealing with security policy and management information base (MIB) content
  • 9. IPsec Services • IPsec provides security services at the IP layer by enabling a system to: • Select required security protocols • Determine the algorithm(s) to use for the service(s) • Put in place any cryptographic keys required to provide the requested services • RFC 4301 lists the following services: • • • • • • Access control Connectionless integrity Data origin authentication Rejection of replayed packets (a form of partial sequence integrity) Confidentiality (encryption) Limited traffic flow confidentiality
  • 11. Security Association (SA) • A one-way logical connection between a sender and a receiver that affords security services to the traffic carried on it • In any IP packet, the SA is uniquely identified by the Destination Address in the IPv4 or IPv6 header and the SPI in the enclosed extension header (AH or ESP) Uniquely identified by three parameters: Security Parameters Index (SPI) • A 32-bit unsigned integer assigned to this SA and having local significance only Security protocol identifier • Indicates whether the association is an AH or ESP security association IP Destination Address • Address of the destination endpoint of the SA, which may be an end-user system or a network system such as a firewall or router
  • 12. Transport and Tunnel Modes Transport Mode • Provides protection primarily for upper-layer protocols • Examples include a TCP or UDP segment or an ICMP packet • Typically used for end-to-end communication between two hosts • ESP in transport mode encrypts and optionally authenticates the IP payload but not the IP header • AH in transport mode authenticates the IP payload and selected portions of the IP header Both AH and ESP support two modes of use: transport and tunnel mode. Tunnel Mode • Provides protection to the entire IP packet • Used when one or both ends of a security association (SA) are a security gateway • A number of hosts on networks behind firewalls may engage in secure communications without implementing IPsec • ESP in tunnel mode encrypts and optionally authenticates the entire inner IP packet, including the inner IP header • AH in tunnel mode authenticates the entire inner IP packet and selected portions of the outer IP header
  • 13.
  • 15. Tunnel Mode and Transport Mode Functionality
  • 16. Authentication header (ah) • Provides support for data integrity and authentication (MAC code) of IP packets. • Guards against replay attacks.
  • 18. Transport Mode (AH Authentication) Tunnel Mode (AH Authentication)
  • 19. Encapsulating security payload (ESP) • ESP provides confidentiality services. • Encryption: • • • • • • Three-key triple DES RC5 IDEA Three-key triple IDEA CAST Blowfish • Authentication: • HMAC-MD5-96 • HMAC-SHA-1-96
  • 20. Transport Mode (ESP Encryption & Authentication) Tunnel Mode (ESP Encryption & Authentication)
  • 21. End-to-end vs end-to-intermediate authentication Transport Mode SA Transport Mode SA Tunnel Mode SA
  • 22. Combining Security Associations • An individual SA can implement either the AH or ESP protocol but not both • Security association bundle • Refers to a sequence of SAs through which traffic must be processed to provide a desired set of IPsec services • The SAs in a bundle may terminate at different endpoints or at the same endpoint • May be combined into bundles in two ways: Transport adjacency • Refers to applying more than one security protocol to the same IP packet without invoking tunneling • This approach allows for only one level of combination Iterated tunneling • Refers to the application of multiple layers of security protocols effected through IP tunneling • This approach allows for multiple levels of nesting
  • 23. Combining Security Associations Possible combinations: a) AH in transport mode. b) ESP in transport mode. c) ESP followed by AH in transport mode. (ESP SA inside AH SA) d) Any a,b or c inside AH or ESP in tunnel mode.
  • 24. Combining Security Associations • Security is provided only between gateways (routers, firewalls, etc.) and no hosts implement IPsec. • Simple VPN support • Tunnel could support AH, ESP or ESP with authentication option
  • 25. Combining Security Associations • • • • Combination of case 1 and case 2 The gateway-to-gateway tunnel provides either authentication, confidentiality, or both for all traffic between end systems. When gateway-to-gateway tunnel is ESP, it also provides limited form of traffic confidentiality. Individual hosts can implement any additional IPsec services required for given applications or given users by means of end-to-end SAs.
  • 26. Combining Security Associations • Combination of case 1 and case 2 • Provides support for a remote host that uses the Internet to reach an organization’s firewall and then to gain access to some server or workstation behind the firewall. • Only tunnel mode is required between the remote host and the firewall.
  • 27. Internet Key Exchange The IPsec Architecture document mandates • The key management support for two types of key management: portion of IPsec • A system administrator involves the manually configures each determination and system with its own keys and distribution of secret with the keys of other communicating systems keys • This is practical for small, • A typical requirement is four keys for communication between two applications • Transmit and receive pairs for both integrity and confidentiality relatively static environments Manual Automated • Enables the on-demand creation of keys for SAs and facilitates the use of keys in a large distributed system with an evolving configuration
  • 28. ISAKMP/Oakley • The default automated key management protocol of IPsec • Consists of: • Oakley Key Determination Protocol • A key exchange protocol based on the Diffie-Hellman algorithm but providing added security • Generic in that it does not dictate specific formats • Internet Security Association and Key Management Protocol (ISAKMP) • Provides a framework for Internet key management and provides the specific protocol support, including formats, for negotiation of security attributes • Consists of a set of message types that enable the use of a variety of key exchange algorithms
  • 29. ISAKMP/Oakley • ISAKMP does not dictate a specific key exchange algorithm; rather ISAKMP consists of a set of message types that enable the use of a variety of key exchange algorithms. • Oakley is the specific key exchange algorithm mandated for use with the initial version of ISAKMP. • Three authentication methods can be used with Oakley: • Digital signatures • Public-key encryption • Symmetric-key encryption
  • 30.
  • 31. Summary • IP security overview • • • • • • • Applications of IPsec Benefits of IPsec Routing applications IPsec documents IPsec services Security associations Transport and tunnel modes • Authentication Header (AH) • Encapsulating Security Payload (ESP) • Combining security associations • Authentication plus confidentiality • Basic combinations of security associations • Internet key exchange • ISAKMP/Oakley • IKE Formats