VPN Protocols

Protocols

There are a number of VPN protocols in use that secure the transport of data traffic over a public network infrastructure. Each protocol varies slightly in the way that data is kept secure.

IP security (IPSec) is used to secure communications over the Internet. IPSec traffic can use either transport mode or tunneling to encrypt data traffic in a VPN. The difference between the two modes is that transport mode encrypts only the message within the data packet (also known as the payload) while tunneling encrypts the entire data packet. IPSec is often referred to as a "security overlay" because of its use as a security layer for other protocols.

Secure Sockets Layer (SSL) and Transport Layer Security (TLS) use cryptography to secure communications over the Internet. Both protocols use a "handshake" method of authentication that involves a negotiation of network parameters between the client and server machines. To successfully initiate a connection, an authentication process involving certificates is used. Certificates are cryptographic keys that are stored on both the server and client.

Point-To-Point Tunneling Protocol (PPTP) is another tunneling protocol used to connect a remote client to a private server over the Internet. PPTP is one of the most widely used VPN protocols because of it's straightforward configuration and maintenance and also because it is included with the Windows operating system.

Layer 2 Tunneling Protocol (L2TP) is a protocol used to tunnel data communications traffic between two sites over the Internet. L2TP is often used in tandem with IPSec (which acts as a security layer) to secure the transfer of L2TP data packets over the Internet. Unlike PPTP, a VPN implementation using L2TP/IPSec requires a shared key or the use of certificates.

VPN technology employs sophisticated encryption to ensure security and prevent any unintentional interception of data between private sites. All traffic over a VPN is encrypted using algorithms to secure data integrity and privacy. VPN architecture is governed by a strict set of rules and standards to ensure a private communication channel between sites. Corporate network administrators are responsible for deciding the scope of a VPN, implementing and deploying a VPN, and ongoing monitoring of network traffic across the network firewall. A VPN requires administrators to be continually be aware of the overall architecture and scope of the VPN to ensure communications are kept private.

Point-to-Point Tunneling Protocol PPTP

The Point-to-Point Tunneling Protocol (PPTP) is a method for implementing virtual private networks. PPTP uses a control channel over TCP and a GRE tunnel operating to encapsulate PPP packets.

The PPTP specification does not describe encryption or authentication features and relies on the PPP protocol being tunneled to implement security functionality. However the most common PPTP implementation, shipping with the Microsoft Windows product families, implements various levels of authentication and encryption natively as standard features of the Windows PPTP stack. The intended use of this protocol is to provide similar levels of security and remote access as typical VPN products.

Specification

A specification for PPTP was published as RFC 2637[1] and was developed by a vendor consortium formed by Microsoft, Ascend Communications (today part of Alcatel-Lucent), 3Com, and others. PPTP has not been proposed nor ratified as a standard by the IETF.

A PPTP tunnel is instantiated by communication to the peer on TCP port 1723. This TCP connection is then used to initiate and manage a second GRE tunnel to the same peer.

The PPTP GRE packet format is non standard, including an additional acknowledgement field replacing the typical routing field in the GRE header. However, like in a normal GRE connection, those modified GRE packets are directly encapsulated into IP packets, and seen as IP protocol number 47.

The GRE tunnel is used to carry encapsulated PPP packets, allowing the tunnelling of any protocols that can be carried within PPP, including IP, NetBEUI and IPX.

In the Microsoft implementation, the tunneled PPP traffic can be authenticated with PAP, CHAP, MS-CHAP v1/v2 or EAP-TLS. The PPP payload is encrypted using Microsoft Point-to-Point Encryption (MPPE) when using MS-CHAPv1/v2 or EAP-TLS. MPPE is described by RFC 3078

Implementations

PPTP was the first VPN protocol that was supported by Microsoft Dial-up Networking. All releases of Microsoft Windows since Windows 95 OSR2 are bundled with a PPTP client, although they are limited to only 2 concurrent outbound connections. Microsoft Windows Mobile 2003 and higher also support the PPTP protocol. The Routing and Remote Access Service for Microsoft Windows contains a PPTP server. The Microsoft implementation uses single DES in the MS-CHAP authentication protocol which many find unsuitable for data protection needs.

Windows Vista and later support the use of PEAP with PPTP. The authentication mechanisms supported are PEAPv0/EAP-MSCHAPv2 (passwords) and PEAP-TLS (smartcards and certificates). Windows Vista removed support for using the MSCHAP-v1 protocol to authenticate remote access connections.

Linux server-side support for PPTP is provided by the PoPToP daemon. and kernel modules for PPP and MPPE. The first PPTP implementation was developed by Matthew Ramsay in 1999. and initially distributed under the GNU GPL by Moreton Bay. However, Linux distributions initially lacked full PPTP support because MPPE was believed to be patent encumbered. Full MPPE support was added to the Linux kernel in the 2.6.14 release on October 28, 2005. SuSE Linux 10 was the first Linux distribution to provide a complete working PPTP client. There is also ACCEL-PPP - PPTP/L2TP/PPPoE server for Linux. which supports PPTP in kernel-mode.

OS X and iOS are bundled with a PPTP client. Cisco and Efficient Networks sell PPTP clients for older Mac OS releases. Palm PDA devices with Wi-Fi are bundled with the Mergic PPTP client.[citation needed]

Many different Mobile phones with Android as operating system support PPTP as well

Security

PPTP has been the subject of many security analyses and serious security vulnerabilities have been found in the protocol. The known vulnerabilities relate to the underlying PPP authentication protocols used, the design of the MPPE protocol as well as the integration between MPPE and PPP authentication for session key establishment.

A summary of these vulnerabilities is below:

    MSCHAP-v1 is fundamentally insecure. Tools exist to trivially extract the NT Password hashes from a captured MSCHAP-v1 exchange.
    When using MSCHAP-v1, MPPE uses the same RC4 session key for encryption in both directions of the communication flow. This can be cryptanalysed with standard methods by XORing the streams from each direction together.
    MSCHAP-v2 is vulnerable to dictionary attack on the captured challenge response packets. Tools exist to perform this process rapidly.
    In 2012 it was shown that brute-force attack on MSCHAP-v2 is equivalent to single DES key brute-force attack. Online service was presented, which is capable to restore MSCHAP-v2 passphrase's MD4 in 23 hours.
    MPPE uses RC4 stream cipher for encryption. There is no method for authentication of the ciphertext stream and therefore the ciphertext is vulnerable to a bit-flipping attack. An attacker could modify the stream in transit and adjust single bits to change the output stream without possibility of detection. These bit flips may be detected by the protocols themselves through checksums or other means.

EAP-TLS is seen as the superior authentication choice for PPTP;  however, it requires implementation of a Public Key Infrastructure for both client and server certificates. As such it is not a viable authentication option for many remote access installations.