IPsec made simple

Understanding IP security protocol (IPsec) terminology and principles can be a hard task due to the wide range of documentation. This tutorial facilitates this task by providing a succinct documentation and a chronological description of the main steps needed to establish an IPsec tunnel.

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IPsec is a set of protocols developed by the IETF to support secure exchange of packets at the IP layer. IPsec includes protocols for establishing mutual authentication between peers at the beginning of the session and negotiation of cryptographic keys to be used during the session. IPsec is available for both IPv4 and IPv6 and has been deployed widely to implement Virtual Private Networks (VPNs). This tutorial covers IKEv1 and IPv4 only.

Interrelationship of IPsec core documents is illustrated in the following schema:

The Architecture document covers the general concepts, security requirements, definitions, and mechanisms defining IPsec technology.

The ESP Protocol and AH Protocol documents cover the packet format and general issues regarding the respective protocols.

The Encryption Algorithms document is the set of documents describing how various encryption algorithms are used for ESP.

The Authentication Algorithm is the set of documents describing how various authentication algorithms are used for both ESP and AH.

The DOI document contains values needed for the other documents to relate to each other. This includes for example encryption algorithms, authentication algorithms, and operational parameters.

The Key Management Documents are the documents describing the IETF standards-track key management schemes (ISAKMP/Oakley, IKE).

How IPsec works

An IPsec tunnel establishment process can be broken down into five main steps: tunnel initiation, IKE Phase 1, IKE Phase 2, data transfer and tunnel termination.

Tunnel initiation: IPsec tunnel initiation can be triggered manually or automatically when network traffic is flagged for protection according to the IPsec security policy configured in the IPsec peers. In both cases, the Internet Key Exchange Protocol (IKE) process starts.

IKE Phase 1, IKE Phase 2: IKE offers a means to automatically negotiate security parameters and derive suitable keying material. IKE also manages the process of re-creating, or refreshing, frequently keys to ensure data confidentiality between peers. The basic operation of IKE can be broken down into two phases: IKE phase 1 and IKE phase 2.

IKE phase 1: This phase is used to negotiate the parameters and key material required to establish an ISAKMP Security Association (ISAKMP SA). The ISAKMP SA is then used to protect future IKE exchanges and to set up a secure channel for negotiating IPsec SAs in IKE phase 2.

IKE Phase 2: This phase is used to negotiate the parameters and key material required to establish two unidirectional IPsec SAs for incoming and outgoing traffic. The IPSEC SAs are then used to protect network traffic during Data transfer phase.

Data transfer: Incoming and outgoing network traffic is encapsulated according to the bundle of algorithms and parameters provided by their respective negotiated IPsec SA to provide confidentiality and authenticity (ESP protocol) or authenticity only (AH protocol).

Tunnel termination: A tunnel is closed when its IPsec SAs terminate through deletion or by timing out. An IPsec SA can time out when a specified number of seconds have elapsed or when a specified number of bytes have passed through the tunnel.

IKE Phase 1

IKE phase 1’s purpose is to establish a secure authenticated communication channel by using the Diffie–Hellman key exchange algorithm to generate a shared secret key to encrypt further IKE communications. This negotiation results in one single bi-directional ISAKMP SA. The authentication can be performed using either pre-shared key (shared secret), digital signatures, or public key encryption as described by RFC 2409.

IKE Phase 1 operates in either Main Mode or Aggressive Mode. Main Mode protects the identity of the peers but Aggressive Mode does not.

Main Mode has three two-way exchanges between the initiator and the receiver.

    • First exchange: The algorithms and hashes used to secure the IKE communications are agreed upon in matching ISAKMP SAs in each peer.
    • Second exchange: Uses a Diffie-Hellman exchange to generate shared secret keying material used to generate shared secret keys and to pass nonces numbers sent to the other party and then signed and returned to prove their identity.
    • Third exchange: Verifies the other side’s identity (the identity value is an IP address, an FQDN, an email address, a DNS or a KEY ID form in encrypted form). The main outcome of main mode is matching ISAKMP SAs between peers to provide a protected pipe for subsequent protected ISAKMP exchanges between the IKE peers. The ISAKMP SA specifies values for the IKE exchange: the authentication method used, the encryption and hash algorithms, the Diffie-Hellman group used, the lifetime of the ISAKMP SA in seconds or kilobytes, and the shared secret key values for the encryption algorithms. The ISAKMP SA in each peer is bi-directional.

Aggressive Mode has fewer exchanges with fewer packets. On the first exchange, almost everything is squeezed into the proposed ISAKMP SA values: the Diffie-Hellman public key (a nonce that the other party signs) and an identity packet, which can be used to verify identity via a third party. The receiver sends everything back that is needed to complete the exchange. The only thing left is for the initiator to confirm the exchange. The weakness of using the aggressive mode is that both sides have exchanged information before there’s a secure channel. Therefore, it’s possible to sniff the wire and discover who formed the new SA. However, it is faster than main mode.

NAT Traversal also known as UDP encapsulation is a general term for techniques that establish and maintain Internet protocol connections traversing network address translation (NAT) gateways and devices. RFC 3947 defines the negotiation during the Internet key exchange (IKE) phase and RFC 3948 defines the UDP encapsulation.

Dead Peer Detection (DPD) is used to monitor the peer and quickly detect when it gets unreachable. It works by exchanging probe packets, and if the peer does not answer for some time, the security associations are killed. DPD is documented by RFC 3706.

XAUTH, Mode config and Hybrid authentication are optional extensions of the IKE phase 1 described in RFC drafts.

Extended Authentication (XAUTH) provides additional user authentication by prompting the user for a username and password.

Mode config is used to deliver parameters such as IP address and DNS address to the client.

Hybrid authentication makes the IKE phase 1 asymmetric: the VPN IPsec server authenticates to the IPsec clients by using a certificate, and the client does not authenticate in IKE phase 1. This extension is usually used with XAUTH to provide a high security level.

IKE Phase 2

The purpose of IKE phase 2 is to negotiate IPsec SAs to set up the IPsec tunnel. IKE phase 2 performs the following functions:

    • Negotiates IPsec SA parameters protected by an existing ISAKMP SA.
    • Establishes IPsec security associations.
    • Periodically renegotiates IPsec SAs to ensure security.
    • Optionally performs an additional Diffie-Hellman exchange.

IKE phase 2 has one mode called quick mode. Quick mode occurs after IKE has established the secure tunnel in IKE phase 1. It negotiates a shared IPsec policy, derives shared secret keying material used for the IPsec security algorithms, and establishes IPsec SAs. Quick mode exchanges nonces that provide replay protection. The nonces are used to generate new shared secret key material and prevent replay attacks from generating bogus SAs.

Quick mode is also used to renegotiate a new IPsec SA when the IPsec SA lifetime expires. Base quick mode is used to refresh the keying material used to create the shared secret key based on the keying material derived from the Diffie-Hellman exchange in IKE phase 1.

If perfect forward secrecy (PFS) is specified in the IPsec policy, a new Diffie-Hellman exchange is performed with each quick mode, providing keying material that has greater entropy (key material life) and thereby greater resistance to cryptographic attacks. Each Diffie-Hellman exchange requires large exponentiations, thereby increasing CPU use and exacting a performance cost.

When the IPsec SAs terminate, the keys are also discarded. When subsequent IPsec SAs are needed for a flow, IKE performs a new IKE phase 2 and, if necessary, a new IKE phase 1 negotiation. A successful negotiation results in new IPsec SAs and new keys. New IPsec SAs can be established before the existing SAs expire, so that a given flow can continue uninterrupted.

Data transfer

IPsec protocols are AH (Authentication Header) and ESP (Encapsulating Security Payloads):
AH is a format protocol defined in RFC 2402 that provides data authentication, integrity, and non repudiation but does not provide data confidentiality. This protocol has largely been superseded by ESP.
ESP is a format protocol defined in RFC 2406 that provides data confidentiality, integrity and data origin authentication, replay attack protection.
ESP supports the use of symmetric encryption algorithms, including DES, 3DES, and AES, for confidentiality and the use of MD5 HMAC and SHA1 HMAC for data authentication and integrity.

AH and ESP protocols support two modes of use: Transport and Tunnel.
Transport mode encrypts only the data portion of each packet, but leaves the header untouched. Tunnel mode is more secure and encrypts both the header and the payload.

The figures below describe the most common ways to encapsulate original IP packets:

Tunnel/Transport modes using AH protocol

 Tunnel/Transport modes using ESP protocol


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