Understanding concepts of VPN

Gundimeda Santosh
8 min readSep 29, 2022

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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 Access:

In addition to the traditional services shown in the figure, enterprises can also use Internet access technologies more commonly used by consumers, including DSL, cable, 4G/5G, and fiber Ethernet. The chapter includes this information about Internet access technologies to provide useful background information before getting into Internet VPN topics.

Digital Subscriber Line (DSL):

Figure below shows some of the details of how DSL works on a home phone line. The phone can do what it has always done: plug into a phone jack and send analog signals. For the data, a DSL modem connects to a spare phone outlet. The DSL modem sends and receives the data, as digital signals, at higher frequencies, over the same local loop, even at the same time as a telephone call.

Because DSL sends analog (voice) and digital (data) signals on the same line, the telco has to somehow split those signals on the telco side of the connection. To do so, the local loop must be connected to a DSL access multiplexer (DSLAM) located in the nearby telco central office (CO). The DSLAM splits out the digital data over to the router on the lower right in Figure, which completes the connection to the Internet. The DSLAM also splits out the analog voice signals over to the voice switch on the upper right.

Cable Internet:

Like DSL, cable Internet takes full advantage of existing cabling, using the existing cable TV (CATV) cable to send data. Like DSL, cable Internet uses asymmetric speeds, sending data faster downstream than upstream, which works well for most consumer locations. And cable Internet still allows the normal service on the cable (cable TV), at the same time as the Internet access service is working.

Cable Internet also uses the same general idea for in-home cabling as DSL, just using CATV cabling instead of telephone cabling. The left side of Figure shows a TV connected to the CATV cabling, just as it would normally connect. At another cable outlet, a cable modem connects to the same cable. The Internet service flows over one frequency, like yet another TV channel, just reserved for Internet service.

Wireless WAN(3G,4G,LTE,5G):

Mobile phones use radio waves to communicate through a nearby mobile phone tower. The phone has a small radio antenna, and the provider has a much larger antenna sitting at the top of a tower somewhere within miles of you and your phone. Phones, tablet computers, laptops, and even routers (with the correct interface cards) can communicate through to the Internet using this technology, as represented in Figure below

Wireless Internet: This general term refers to Internet services from a mobile phone or from any device that uses the same technology.

3G/4G Wireless: Short for third generation and fourth generation, these terms refer to the major changes over time to the mobile phone companies’ wireless networks.

LTE: Long-Term Evolution is a newer and faster technology considered to be part of fourth generation (4G) technology.

5G Wireless: This is the fifth major generation of wireless phone technology.

Fiber Internet Access:

The consumer-focused Internet access technologies discussed in this section use a couple of different physical media. DSL uses the copper wiring installed between the telco CO and the home. Cable uses the copper CATV cabling installed from the cable company to the home. And, of course, wireless WAN technologies do not use cables for Internet access.

The cabling used by DSL and cable Internet uses copper wires, but, comparing different types of physical media, fiber-optic cabling generally supports faster speeds for longer distances. That is, just comparing physical layer technologies across the breadth of networking, fiber-optic cabling supports longer links, and those links often run at equivalent or faster speeds.

Internet VPN fundamentals:

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

Anti-replay: 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.

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

1. Host PC1 (10.2.2.2) on the right sends a packet to the web server (10.1.1.1), just as it would without a VPN.

2. The router encrypts the packet, adds some VPN headers, adds another IP header (with public IP addresses), and forwards the packet.

3. 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.

4. 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.

5. Server S1 receives the unencrypted packet.

Site-to-Site VPN’s with IPsec:

The above figure is an example of Site-to-Site i.e., there is a single tunnel in between two sites.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 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 encryption example of IPsec can be as shown in the above 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:

1. The sending VPN device (like the remote office router in Figure above) feeds the original packet and the session key into the encryption formula, calculating the encrypted data.

2. The sending device encapsulates the encrypted data into a packet, which includes the new IP header and VPN header.

3. The sending device sends this new packet to the destination VPN device (FW1 back in Figure above).

4. 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.

Figure above 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.

Remote Access VPNs with TLS:

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.

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 Any Connect Secure Mobility Client (or Any Connect 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 above 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.

The bottom of Figure above 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.

The table below serves as a comparison between the different vpn clients.

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