1.

Collision domains are unsecure

2. The employees often need to remote access to
corporate network resources
 The Internet traffic is much more vulnerable to
eavesdropping than the one that runs in an internal
company network (think at a hotel wifi).
3. More remote offices may need to have access to
the same resources
 Idea: creating a collision domain using a artificial
underlying physical network (Internet) as the transmission
media and through a tunneling protocol encapsulating the
data to be transmitted (and possibly encrypting it)
 Goal: get a transparent and secure subnet at low cost

 a secure tunnel is created

from the point of origin to
the arrival
 data can be transmitted
both encrypted and signed
 The term is generic, it can describe different
configurations of networks and protocols ...
 Virtual: it is an artificial network that relies on an
underlying physical network
 Private: data is transmitted encapsulated and ensuring
some form of confidentiality
 It works as a “pipe within a pipe” where the outside is
formed by the connection of the underlying network
◦ Internet can be used as a communication platform
◦ Establishes the logical channels that are totally logic and safe
between sections
 Data encryption
 Confidential communications

 Verifiability of the identity of each station

 Authentication mechanisms

 The remote sections logically belong to the same

local network as the central section
 Users can access all applications and databases of the
central section, as if they were physically on the same
LAN
 Cost reduction (for the use of the Internet)
 Connecting remote locations without the costs of a dedicated
line
 Scalability
 Add a potentially unlimited number of new sections or
roadwarriors
 Security and protection of data transmitted over the
network
 Possibility to access the corporate network users outside
the company
 Protocol independent, no need to support SSL at layer 4/5
 Overhead and loss of bandwidth
 Configuration far from automatic
 Vulnerabilities exist, they are not the universal
solution
 If used also as a proxy service, ONLY the
virtual link between client and VPN server is
under protection
 Type of Tunneling protocol
 Localization of the "tunnel termination“
 user side (LAN) or network provider
 Access type
 site-to-site, remote access connectivity
 Guaranteed security level
 OSI layer that is exposed to the network
connection
 Layer 2 circuits, Layer 3 network connectivity
 Intranet VPN: connecting remote offices or
locations of a company
 Remote access VPN: connect head office of a
company with remote or mobile users
 Extranet VPN: connect the central office with
partners, customers, suppliers
◦ Intranet VPN: information security, performance of
responses, scalability
◦ Remote VPN access: strong authentication, efficient
system of centralized account management
◦ Extranet VPN: use of standard and open platforms
 Authentication mechanisms for the endpoints of
the tunnel (during the setup of the tunnel)
 Transit traffic encryption
 The traffic is encrypted and this creates a
"Tunnel" between two networks / hosts
 The "Secure VPN" have one or more tunnels and
each tunnel has two endpoints
 To be called Secure, a VPN must provide:
 an authentication system
 the data must be transmitted encrypted
 Cryptography must be strong and can be changed
over time
 Are used:
 to protect the traffic when the Internet is the network of
support or if the level of security offered by the
underlying network differs from that required by domestic
traffic to the VPN

 In a remote access scenario, where a VPN client (end

user) connects securely to a remote office network
 For example, utilities offer remote access to employees of an
organization
 Technologies and protocols used (some non-
standard IETF)
 SSH Tunneling
 SSL/TLS VPN (with SSL/TLS)
 OpenVPN
 PPTP/SSTP (with MPPE).
 IPsec ‘pure’
 Ipsec+L2TP
 Ipsec (Internet Protocol Security)

 Developed for IPv6, but also used for IPv4

 Introduction of security
 Traffic encryption: traffic read only by target
 Integrity
 Authentication of peers
 IPsec (Internet Protocol Security)
 Standard
 Encapsulating Security Payload (ESP): provides
authentication, confidentiality and integrity check of the
message;
 Authentication Header (AH): ensures authentication and
integrity of the messagebut does not offer the confidentiality;
 Internet key exchange (IKE): implements "exchange keys" to
realize the encrypted stream;
 AH authenticates the complete package, instead ESP
authenticates data only.
iptables –A FORWARD –i eth1 –p tcp –dport 22 –j ACCEPT
iptables –A FORWARD –i eth0 –p tcp –sport 22 \
–m state –state ESTABLISHED, RELATED–j ACCEPT
iptables –A FORWARD –p 47 –j ACCEPT
iptables –A FORWARD –i eth1 –p tcp –-dport 1723 \
–m state –state ESTABLISHED, RELATED–j ACCEPT
iptables –FORWARD –eth0 –p tcp –-sport 1723 \
–m state –state ESTABLISHED, RELATED–j ACCEPT
iptables –A FORWARD –p esp –j ACCEPT
iptables –A FORWARD –i eth1 –p udp –-dport 500 \
–m state –state ESTABLISHED, RELATED–j ACCEPT
iptables –A FORWARD –i eth0 –p udp –-sport 500 \
–m state –state ESTABLISHED, RELATED–j ACCEPT
 set of network protocols
 a protocol is encapsulated in another of equal or
higher layer
The tunneling creates virtual circuits
where network traffic is transmitted
 Protocols used for the Tunneling:
 L2TP (Layer 2 Tunneling Protocol)
 MPLS (Multi-Protocol Label Switching)
 GRE (Generic Routing Encapsulation)
 PPTP(Point-to-Point Tunneling Protocol)
 Ipsec
 IEEE 802.1Q (Ethernet VLANs)
Point to Point Tunneling Developed by Microsoft, is a Point to Point Protocol
Protocol (PPTP) (PPP) extension that encapsulates IP, IPX, NetBEUI
into IP packets
Layer 2 Forwarding (L2F) Developed by Cisco, used for the “tunneling” of link
protocols
Layer 2 Forwarding Protocol Created with an agreement to Microsoft and Cisco,
(L2TP) allows the “tunneling” of PPP traffic on serveral
network. Gives a multi-protocol dial-up service for ISP
and POP provider.
As L2F, L2TP does not provide encryption.

Socksv5 L2TP alternative developed by Nec

 Transport Layer Security (SSL/TLS)
◦ Can be used for tunneling the entire network traffic (SSL/TLS
VPN) or to make it secure a individual connection
◦ SSL (essential for providing remote access to VPN services)
 Advantage of SSL VPN is that it can also be accessed from locations that
restrict access to SSL-based Web sites without the support of IPsec.
 SSL-based VPNs may be vulnerable to denial-of-service targeted to TCP
connections, being unauthenticated
◦ Ensures confidentiality and reliability of communications over a
public network
◦ Protects from intrusion, alteration or falsification
 Datagram Transport Layer Security (DTLS)
◦ Cisco AnyConnect VPN.
◦ DTLS resolve tunneling problem on TCP, in the same way SSL /
TLS
 Microsoft Point-to-Point Encryption (MPPE)
◦ Used with PPTP
◦ PPTP (point-to-point tunneling protocol):
 Data encryption
 Developed by Microsoft, ensures authentication, encryption and
compression of data
◦ Generic Routing Encapsulation (GRE): GRE creates a virtual
link point-to-point and this is done in a way that none of the two
ends have to worry about the infrastructure on which the
communication passes
 Secure Socket Tunneling Protocol (SSTP)
(Microsoft)
◦ Windows Server 2008, Windows Vista Service Pack 1.
◦ SSTP tunnels PPP o L2TP traffic via a SSL 3.0 channel
 MPVPN (Multi Path Virtual Private Network)
◦ Developed by Ragula Systems Development Company
 SSH VPN -- OpenSSH
◦ Provides VPN tunneling to ensure secure remote
connections to a network
 L2TP (Layer 2 Tunnelling Protocol)
◦ Secure/Trusted VPN
◦ Standard IETF
◦ Is a layer 5 protocol (session) that works as a layer 2 protocol
(data link) using UDP packets to encapsulate L2TP packets and
to maintain a Point-to-Point connection.
◦ Has to be combined with another protocol to implement
authentication, confidentiality and integrity of data (usually
IPSec).
 L2TPv3 (Layer 2 Tunnelling Protocol version 3)
◦ Secure/Trusted VPN
◦ Evoluzione di L2TP creato come alternativa a MPLS
 Data confidentiality: Encrypts packets before transmission (ESP)
 Data integrity: Authenticates packets to help ensure that the data has
not been altered during transmission
 Data origin authentication: Authenticates the source of received
packets, in conjunction with data integrity service (Internet Key
Exchange protocol)
 Antireplay: Detects aged or duplicate packets, rejecting them
 Alternative to IPSec for remote-access VPNs
 SSL provides access special client software
 Secure connectivity by authenticating the communicating parties
and encrypting the traffic
 SSL operates at the session layer and doesn’t not support
applications not coded for SSL
 SP can provide granular access control, limiting individual users'
access to resources
 Include application proxies (SSL must be aware of each individual
connection )
 SSL is computing-intensive
(encryption processes )
 The tunnel endpoints have to authenticate
before establish a secure VPN circuit
 Tunnel End user-created can use passwords,
biometrics, two-factor authentication, other
encryption methods
 Network-to-network tunnels using passwords or
digital certificates, since it must be stored
permanently and does not require manual
intervention for the activation of the tunnel.