VPN

Virtual Private Network

國立陽明交通大學資工系資訊中心
Computer Center of Department of Computer Science, NYCU
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Introduction
● Uses public telecommunication channels, such as the Internet or
other network service, instead of leased lines channels.
● Described as Virtual because it is distant connection using private
connections.
● Used to widely now because of today's globalization.
● Connects users or branches.
● Used to use dial-up or Leased communication, now using IP-VPN’s

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What is VPN
● Extension of a private network that encompasses links across
shared or public networks like the Internet.
● Enable to send data between two computers across a shared or
public internetwork in a manner that emulates the properties of a
point-to-point private link.

Tunnel VPN Connection VPN

VPN Server Client
Internet
Firewall

Web Server

Private Network
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Common Uses of VPNs (1/3)
1. Remote Access Over the Internet

Virtual Private Networking: An Overview | Microsoft Docs 4

Common Uses of VPNs (2/3)
2. Connecting Networks Over the Internet (Site to Site VPN)

Virtual Private Networking: An Overview | Microsoft Docs 5

Common Uses of VPNs (3/3)
3. Connecting Computers over an Intranet (similar to 1.)

Virtual Private Networking: An Overview | Microsoft Docs 6

Why Use VPN?
● Cheap
○ Legacy private network uses remote connectivity through dial-up
modems or through leased line connections, it’s expensive.
● Scalable
○ Extending a leased line connection is complex.
○ Easy to administer.
● Security
○ Provide encryption and file integrity.

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VPN Key Concept - Tunneling
● VPN consists of a set of point to point connections tunneled over
the Internet.
● In order to achieve tunneling, the packets are encapsulated as the
payload of packets.
○ Payloads, to and from addresses, port numbers and other standard
protocol packet headers
○ As seen by the external routers carrying the connection
Tunnel Endpoint

Transit Internetwork Header

Host Host
Payload Payload
Tunneled Payload Transit Internet work
Tunnel
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Basic VPN Requirements
● User Authentication
● Key Management
● Address Management
● Data Encryption

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Basic VPN Requirements (1/2)
● User Authentication
○ Verify the VPN client's identity and restrict VPN access to authorized
users only.
○ Provide audit and accounting records to show who accessed what
information and when.
○ X.509, pre-shared key, etc.
● Key Management
○ Generate and refresh encryption keys for the client and the server.
○ Simple Key Management for IP: ISAKMP/Oakley, etc.

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Basic VPN Requirements (2/2)
● Address Management
○ Assign a VPN client's address on the intranet and ensure that private
addresses are kept private
● Data Encryption
○ No one outside the VPN can alter the VPN.
○ Data carried on the public network must be rendered unreadable to
unauthorized clients on the network.

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VPN Security
● Authentication
○ Ensuring that the data originates at the source that it claims.
● Access Control
○ Restricting unauthorized users from gaining admission to the
network.
● Confidentiality
○ Preventing anyone from reading or copying data as it travels across
the Internet.
● Data Integrity
○ Ensuring that no one tampers with data as it travels across the
Internet.
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Common Implementations
● Based on PPP
○ Point-to-Point Tunneling Protocol (PPTP) (PPP + encryption + GRE)
○ Layer Two Tunneling Protocol (L2TP) (PPTP + L2F)
● Based on TCP/IP
○ L2TP/IPsec
○ IPsec Tunnel mode [RFC 4301]
○ BGP/MPLS IP VPN [RFC 4364]
● SSL/TLS
○ Secure Socket Tunneling Protocol (SSTP) (PPTP + SSL)
○ SSL VPN
○ OpenVPN
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PPP - Point-to-Point Protocol
● PPP [RFC 1661] provides a standard method for transporting multi-protocol
datagrams over point-to-point (direct) links.
○ Data link layer (layer 2) protocol
● Three components
○ Encapsulation (for transporting purpose)
○ Link Control Protocol (for data-link connectability)
○ Network Control Protocols (NCP) family (L3 management support)
● Extra Options
○ Authentication: PAP, CHAP, EAP, MS-CHAP, MS-CHAPv2, etc.
○ Link Quality and error detection
○ Compression
○ Encryption: MPPC + MPPE, etc.
○ Multilink (MP, The PPP Multilink Protocol)
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Tunneling Protocol
● Allows a network user to access or provide a network service that the
underlying network does not support or provide directly. (Wikipedia)
● GRE (Generic Routing Encapsulation): Establish a virtual point-to-
point connection between two networks.
○ IP as a delivery protocol
○ Virtual Tunnel: (Tunnel) IP header + GRE packet header
○ Encapsulation, not encryption
● PPTP / L2TP
● IPsec
● OpenVPN (with SSL/TLS)
● etc.
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PPTP - Point-to-Point Tunneling Protocol
● PPTP [RFC 2637] uses an enhanced GRE mechanism to provide a
flow- and congestion-controlled (TCP) encapsulated datagram
service for carrying PPP packets.
● PPTP creates a GRE tunnel through which the PPTP GRE packets
are sent.

Encrypted

IP GRE PPP PPP payload

header header header (IP datagram, IPX datagram, MetBEUI frame)

PPP frame

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Security of PPTP
● PPTP has been the subject of many security analyses and
● serious security vulnerabilities have been found
○ MS-CHAP is fundamentally insecure.
○ MS-CHAPv2 is vulnerable to dictionary attack on the captured
challenge response packets.
● The PPP payload can be encrypted by using Microsoft Point to
Point Encryption (MPPE) when using MS-CHAPv1/v2
● EAP-TLS (Extensible Authentication Protocol – TLS) is the
superior authentication choice for PPTP.

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L2TP - Layer Two Tunneling Protocol
● L2TP [RFC 2661]: PPTP + L2F (Layer Two Forwarding)
● High level protocols (e.g., PPP) establish L2TP session (“call”) within the L2TP
tunnel, and traffic for each session is isolated.
● A tunnel can contains multiple connections at once.
● L2TP over IP internetworks uses UDP and a series of L2TP messages for tunnel
maintenance.
● L2TPv3 provides additional security features, improved encapsulation, and the
ability to carry data links other than simply PPP over an IP network. (Wikipedia)

IP UDP L2TP PPP PPP payload

header header header header (IP datagram, IPX datagram, MetBEUI frame)

PPP frame

L2TP frame

UDP message 18
L2TP/IPsec
● L2TP does not provide confidentiality or strong authentication.
● Usually use IPsec ESP (Encapsulating Security Payload) to encrypt the L2TP packet.
○ Data encryption begins before the PPP connection process by negotiating an IPSec security
association.
○ Require computer-level authentication using computer certificates.

IP UDP L2TP PPP PPP payload

header header header header (IP datagram, IPX datagram, MetBEUI frame)

IPSec IPSec IPSec

IP UDP L2TP PPP PPP payload
ESP ESP Auth
header header header header (IP datagram, IPX datagram, MetBEUI frame)
header trailer trailer

Encrypted by IPSec

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IPsec
● IPsec [RFC 4301] is a secure network protocol suite provides authentication and
encryption ability over IPv4 network.
● Two modes in IPsec
○ Transport mode: Insert IPsec header (AH/ESP) between IP and TCP header, then modify
original IP header.
○ Tunnel mode: Encapsulate original packet, and prepend new IP and IPsec header.
● Two functions that ensure confidentiality:
○ Authentication Header (AH)
■ Provide source authentication and integrity without encryption.
○ Encapsulating Security Payload (ESP)
■ Provide both data authentication, data integrity and data encryption.
● Security Associations (SA) provides the parameters necessary for AH and/or ESP
operations.
○ IKE (Internet Key Exchange): Provide authentication and key exchange. e.g., ISAKMP,
OAKLEY 20
IPsec Modes

IPsec VPN Theory | Cisco Routing & Switching and Security ([Link]) 21
SSL VPN
● A form of VPN that can be used with a standard Web browser.
○ Also can be used to tunnel traffic via SSL or TLS protocol
● The traffic is encrypted with the SSL protocol or Transport Layer
Security (TLS) protocol.
● Proprietary software
○ Cisco AnyConnect
○ Juniper Networks Pulse Secure
○ Fortigate
● Open Source
○ OpenVPN

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Appendix
● I Am Anonymous When I Use a VPN – 10 Myths Debunked
● Virtual Private Networking: An Overview
● BeyondCorp by Google: Protected connection from untrusted networks without
the use of a VPN.
○ See also: Role-Based Access Control (RBAC)
● Protocol reference
○ VPN
○ PPP / GRE / PPTP / L2TP
○ IPsec / IKE
○ IP protocol numbers

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