Describe remote access and site-to-site VPNs

Describe remote access and site-to-site VPNs

To build the Internet, Internet service providers (ISP) need links to other ISPs as well as links to the ISPs’ customers. The Internet core connects ISPs to each other using a variety of highspeed technologies. Additionally, Internet access links connect an ISP to each customer, again with a wide variety of technologies. The combination of ISP networks and customer networks that connect to the ISPs together create the worldwide Internet.

For these customer access links, the technologies need to be inexpensive so that a typical consumer can afford to pay for the service. But businesses can use many of these same technologies to connect to the Internet. Some WAN technologies happen to work particularly well as Internet access technologies. For example, several use the same telephone line installed into most homes by the phone company so that the ISPs do not have to install additional cabling. Some use the TV cabling, whereas others use wireless. While consumers typically connect to the Internet to reach destinations on the Internet, businesses can also use the Internet as a WAN service. First, the enterprise can connect each business site to the Internet. Then, using virtual private network (VPN) technology, the enterprise can create an Internet VPN. An Internet VPN can keep the enterprise’s packet private through encryption and other means, even while sending the data over the Internet.

Internet VPN Fundamentals

Private WANs have some wonderful security features. In particular, the customers who send data through the WAN have good reason to believe that no attackers saw the data in transit or even changed the data to cause some harm. The private WAN service provider promises to send one customer’s data to other sites owned by that customer, but not to sites owned by other customers, and vice versa. VPNs try to provide the same secure features as a private WAN while sending data over a network that is open to other parties (such as the Internet). Compared to a private WAN, the Internet does not provide for a secure environment that protects the privacy of an enterprise’s data. Internet VPNs can provide important security features, such as the following:

  • Confidentiality (privacy): Preventing anyone in the middle of the Internet (man in the middle) from being able to read the data
  • Authentication: Verifying that the sender of the VPN packet is a legitimate device and not a device used by an attacker
  • Data integrity: Verifying that the packet was not changed as the packet transited the Internet
  • Antireplay: Preventing a man in the middle from copying and later replaying the packets sent by a legitimate user, for the purpose of appearing to be a legitimate user.

To accomplish these goals, two devices near the edge of the Internet create a VPN, sometimes called a VPN tunnel. These devices add headers to the original packet, with these headers including fields that allow the VPN devices to make the traffic secure. The VPN devices also encrypt the original IP packet, meaning that the original packet’s contents are undecipherable to anyone who happens to see a copy of the packet as it traverses the Internet.

Figure shows the general idea of what typically occurs with a VPN tunnel. The figure shows a VPN created between a branch office router and a Cisco firewall. In this case, the VPN is called a site-to-site VPN because it connects two sites of a company.

The figure shows the following steps, which explain the overall flow:

  • Host PC1 ( on the right sends a packet to the web server (, just as it would without a VPN.
  • The router encrypts the packet, adds some VPN headers, adds another IP header (with public IP addresses), and forwards the packet.
  • An attacker in the Internet copies the packet (called a man-in-the-middle attack). However, the attacker cannot change the packet without being noticed and cannot read the contents of the original packet.
  • Firewall FW1 receives the packet, confirms the authenticity of the sender, confirms that the packet has not been changed, and then decrypts the original packet.
  • Server S1 receives the unencrypted packet.

The benefits of using an Internet-based VPN are many. The cost of a high-speed Internet access connection as discussed in the last few pages is usually much less than that of many private WAN options. The Internet is seemingly everywhere, making this kind of solution available worldwide. And by using VPN technology and protocols, the communications are secure.

Site-to-Site VPNs with IPsec

A site-to-site VPN provides VPN services for the devices at two sites with a single VPN tunnel. For instance, if each site has dozens of devices that need to communicate between sites, the various devices do not have to act to create the VPN. Instead, the network engineers configure devices such as routers and firewalls to create one VPN tunnel. The tunnel endpoints create the tunnel and leave it up and operating all the time, so that when any device at either site decides to send data, the VPN is available. All the devices at each site can communicate using the VPN, receiving all the benefits of the VPN, without requiring each device to create a VPN for themselves.

IPsec defines one popular set of rules for creating secure VPNs. IPsec is an architecture or framework for security services for IP networks. The name itself is not an acronym, but rather a name derived from the title of the RFC that defines it (RFC 4301, “Security Architecture for the Internet Protocol”), more generally called IP Security, or IPsec. IPsec defines how two devices, both of which connect to the Internet, can achieve the main goals of a VPN as listed at the beginning of this section: confidentiality, authentication, data integrity, and anti-replay. IPsec does not define just one way to implement a VPN, instead allowing several different protocol options for each VPN feature. One of IPsec’s strengths is that its role as an architecture allows it to be added to and changed over time as improvements to individual security functions are made.

The idea of IPsec encryption might sound intimidating, but if you ignore the math—and thankfully, you can—IPsec encryption is not too difficult to understand. IPsec encryption uses a pair of encryption algorithms, which are essentially math formulas, to meet a couple of requirements. First, the two math formulas are a matched set:

  • One to hide (encrypt) the data
  • Another to re-create (decrypt) the original data based on the encrypted data

Besides those somewhat obvious functions, the two math formulas were chosen so that if an attacker intercepted the encrypted text but did not have the secret password (called an encryption key), decrypting that one packet would be difficult. In addition, the formulas are also chosen so that if an attacker did happen to decrypt one packet, that information would not give the attacker any advantages in decrypting the other packets. The process for encrypting data for an IPsec VPN works generally as shown in Figure, Note that the encryption key is also known as the session key, shared key, or shared session key.

The four steps highlighted in the figure are as follows:

  • The sending VPN device feeds the original packet and the session key into the encryption formula, calculating the encrypted data.
  • The sending device encapsulates the encrypted data into a packet, which includes the new IP header and VPN header.
  • The sending device sends this new packet to the destination VPN device.
  • The receiving VPN device runs the corresponding decryption formula, using the encrypted data and session key—the same key value as was used on the sending VPN device—to decrypt the data.

While above describes the basic encryption process, Below figure shows a broader view of IPsec VPNs in an enterprise. First, devices use some related VPN technology like Generic Routing Encapsulation (GRE) to create the concept of a tunnel (a virtual link between the routers), with three such tunnels shown in the figure. Without IPsec, each GRE tunnel could be used to forward unencrypted traffic over the Internet. IPsec adds the security features to the data that flows over the tunnel. (Note that the figure shows IPsec and GRE, but IPsec teams with other VPN technologies as well.)

Remote Access VPNs with TLS

A site-to-site VPN exists to support multiple devices at each site and is typically created by devices supported by the IT staff. In contrast, individual devices can dynamically initiate their own VPN connections in cases where a permanent site-to-site VPN does not exist. For instance, a user can walk into a coffee shop and connect to the free Wi-Fi, but that coffee shop does not have a site-to-site VPN to the user’s enterprise network. Instead, the user’s device creates a secure remote access VPN connection back to the enterprise network before sending any data to hosts in the enterprise. While IPsec and GRE (or other) tunnels work well for site-to-site VPNs, remote access VPNs often use the Transport Layer Security (TLS) protocol to create a secure VPN session.

TLS has many uses today, but most commonly, TLS provides the security features of HTTP Secure (HTTPS). Today’s web browsers support HTTPS (with TLS) as a way to dynamically create a secure connection from the web browser to a web server, supporting safe online access to financial transactions. To do so, the browser creates a TCP connection to server well-known port 443 (default) and then initializes a TLS session. TLS encrypts data sent between the browser and the server and authenticating the user. Then, the HTTP messages flow over the TLS VPN connection.

The built-in TLS functions of a web browser create one secure web browsing session, but each session secures only the data sent in that session. This same TLS technology can be used to create a client VPN that secures all packets from the device to a site by using a Cisco VPN client. The Cisco AnyConnect Secure Mobility Client (or AnyConnect Client for short) is software that sits on a user’s PC and uses TLS to create one end of a VPN remote-access tunnel. As a result, all the packets sent to the other end of the tunnel are encrypted, not just those sent over a single HTTP connection in a web browser.

Figure compares the option to create a VPN remote access VPN session from a computer to a site versus for a single HTTPS session. The figure shows a VPN tunnel for PC using the AnyConnect Client to create a client VPN. The AnyConnect Client creates a TLS tunnel to the firewall that has been installed to expect VPN clients to connect to it. The tunnel encrypts all traffic so that PC A can use any application available at the enterprise network on the right.

Note that while the figure shows a firewall used at the main enterprise site, many types of devices can be used on the server side of a TLS connection as well. The bottom of Figure shows a client VPN that supports a web application for a single web browser tab. The experience is much like when you connect to any other secure website today: the session uses TLS, so all traffic sent to and from that web browser tab is encrypted with TLS. Note that PC B does not use the AnyConnect Client; the user simply opens a web browser to browse to server S2.

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