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350-701Chapter 9 of 18Objective 2.4

Site-to-Site VPN Technologies

Site-to-site VPN technologies solve the problem of connecting two separate company networks securely across the public internet. This matters because businesses have offices in different locations that need to share resources like files, emails, and databases as if they were in the same building. For the 350-701 exam, you must understand how these technologies work and why they are used.

12 min read
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Updated Jul 23, 2026
Reviewed by Johnson Ajibi· Senior Network & Security Engineer · MSc IT Security

A simple way to picture Site-to-Site VPN Technologies

The Diplomatic Courier Analogy

A diplomatic courier is responsible for securely transporting a sealed diplomatic bag between two embassies. The two embassies are in different cities, and the courier must travel through public roads and airports where anyone could try to open the bag or intercept it. The courier never carries the bag's contents exposed; everything is inside a tamper-proof, locked pouch. The bag itself is encrypted: only the sending and receiving ambassadors have the keys to open it. The courier's route is a dedicated, secure path through the public environment. This is exactly what a site-to-site VPN does. The two embassies are the two company offices or sites. The public roads are the internet. The diplomatic bag is the encrypted data. The courier is the VPN gateway device at each site. The bag's lock is the encryption algorithm. The keys are the pre-shared keys or digital certificates used to encrypt and decrypt the traffic. The entire journey is the VPN tunnel: a secure, private connection over a public network. No one else can read the letters inside the bag, even if they intercept it. Similarly, a site-to-site VPN protects company data as it travels across the internet between two sites.

How It Actually Works

A site-to-site Virtual Private Network (VPN) is a secure connection between two or more entire networks over a public network, usually the internet. The key idea is that the VPN creates a 'tunnel' through the public internet. All data passing through this tunnel is encrypted so that no one else can read or modify it. This allows two offices to behave as if they are on the same private network, even though they might be in different countries.

The most common technology for implementing site-to-site VPNs is IPsec (Internet Protocol Security). IPsec provides two main services: encryption to keep data secret, and authentication to ensure that the data comes from a trusted source and has not been tampered with. IPsec operates in two modes: tunnel mode and transport mode. In tunnel mode, the entire original IP packet (including its header) is encrypted and placed inside a new IP packet. This is the mode used for site-to-site VPNs. In transport mode, only the payload of the packet is encrypted, which is more commonly used for end-to-end connections between individual devices.

When using IPsec for a site-to-site VPN, the process begins with two VPN gateways (the devices at each site, often routers or firewalls) establishing a secure connection. This is done through a series of steps called the Internet Key Exchange (IKE). IKE has two phases. Phase 1 creates a secure, but not yet tunnel-ready, channel between the two gateways. They authenticate each other using a pre-shared key (a secret password shared in advance) or digital certificates. Phase 2 establishes the actual IPsec tunnel and negotiates the encryption keys and algorithms that will be used for the data traffic.

Once the tunnel is set up, all traffic between the two networks is encapsulated and encrypted at one end and decapsulated and decrypted at the other. Imagine sending a sealed envelope inside a locked box. The box goes through the public mail system, but only the intended recipient has the key to open the box and read the envelope. The network devices at each site handle this without the users needing to think about it.

There are different types of site-to-site VPN technologies. The most traditional is the policy-based VPN, where the administrator defines rules about which traffic should be encrypted (e.g., traffic between the 192.168.1.0 network and the 10.0.0.0 network). The second is the route-based VPN, which uses a virtual tunnel interface (VTI). In this model, you create a virtual interface on the router, and you use routing protocols to decide which traffic goes into the tunnel. This is more flexible and easier to manage at scale.

Another important concept is the difference between a full mesh and a hub-and-spoke VPN. In a full mesh, every site can connect directly to every other site. This is good for performance but becomes complicated when you have many sites. In a hub-and-spoke, all sites connect to a central hub site. Remote offices connect through the hub to reach each other, which simplifies management but can create a bottleneck.

Why does this matter? Before site-to-site VPNs, companies had to lease dedicated private lines (leased lines) from telecom providers to securely connect offices. This was extremely expensive. Site-to-site VPNs replaced those expensive leased lines by using the cheaper internet, while still providing the same level of security through encryption. For the 350-701 exam, you should also understand that site-to-site VPNs are not the same as remote-access VPNs, which allow individual employees to connect from their home computers to the office. In a site-to-site VPN, the two networks are always connected, so resources are always available to both offices, just like a single large network.

A simple flowchart showing two networks connected through VPN gateways over the internet with an encrypted IPsec tunnel.

Walk-Through

1

Define the networks

Identify the IP address ranges (subnets) at each site. For example, Site A uses 192.168.1.0/24 and Site B uses 192.168.2.0/24. This determines which traffic should be encrypted.

2

Configure IKE Phase 1

Set up the parameters for the secure management channel. This includes choosing an encryption algorithm (e.g., AES-256), an integrity algorithm (e.g., SHA-256), an authentication method (e.g., pre-shared key), and a Diffie-Hellman group for key exchange.

3

Configure IKE Phase 2

Define the actual IPsec tunnel parameters: which traffic is allowed (the interesting traffic), the encryption and integrity algorithms for the data, and the lifetime of the tunnel. This phase creates the encryption keys for the data stream.

4

Apply the configuration to the VPN gateways

Enter the commands or use a GUI to apply the Phase 1 and Phase 2 policies to each site's firewall or router. Ensure both devices have matching settings.

5

Test and verify the tunnel

Use commands like 'ping' from a device on one network to a device on the other network over the VPN. Check the VPN status with 'show crypto isakmp sa' (Phase 1) and 'show crypto ipsec sa' (Phase 2) on Cisco devices. Verify that packets are being encrypted and decrypted.

What This Looks Like on the Job

An IT professional securing a company with two branch offices needs to connect the main office in London to a branch office in Manchester so that employees in Manchester can access the company's central file server and database. Instead of paying for an expensive private leased line, the IT professional will configure a site-to-site IPsec VPN between the two office firewalls.

Here is what happens step by step:

First, the IT professional identifies the public IP addresses of the two firewalls. The London firewall has a public IP address of 203.0.113.1, and the Manchester firewall has 198.51.100.1. These are the addresses on the internet side of the network.

Next, they configure the IKE settings on both firewalls. This includes setting the same pre-shared key (a complex password like 'L0nd0n2M@nch3st3r!') and choosing encryption algorithms. The 350-701 exam often tests which algorithms are secure, such as AES-256 for encryption and SHA-256 for integrity.

The IT professional then defines the IPsec policy. This specifies exactly which traffic should be encrypted. For example, traffic from the London subnet (192.168.1.0/24) to the Manchester subnet (192.168.2.0/24) must go through the tunnel. This is a policy-based VPN.

After configuration, the IT professional tests the VPN. They ping a device in Manchester from London. If the ping succeeds, the tunnel is working. They will also use tools like 'show crypto isakmp sa' and 'show crypto ipsec sa' on Cisco devices to verify that both phases of IKE have completed successfully.

A common issue the IT professional must troubleshoot is a mismatch in the pre-shared key or encryption algorithms. If one site uses AES-256 and the other uses AES-128, the tunnel will not come up. The IT professional must ensure both ends agree on every parameter.

Finally, the IT professional monitors the VPN for stability. They set up logging to detect if the tunnel drops and configure recovery options like Dead Peer Detection (DPD), which automatically rebuilds the tunnel if it fails.

This scenario shows the practical steps involved. The IT professional does not need to worry about each packet's route through the internet; the VPN handles that. Their job is to configure the gateways correctly, choose strong security parameters, and monitor the connection for issues.

How 350-701 Actually Tests This

The 350-701 exam tests your knowledge of site-to-site VPN technologies through multiple-choice questions and scenario-based questions. They will ask you to select the correct protocol, the correct configuration option, or the correct troubleshooting step. Here is exactly what you need to focus on:

Concepts you must know by heart:

The difference between IPsec tunnel mode and transport mode. The exam loves to ask: 'Which mode is used for a site-to-site VPN?' The answer is tunnel mode.

The two phases of IKE. Phase 1 uses UDP port 500 and establishes a secure management channel. Phase 2 uses UDP port 4500 (for NAT traversal) or 500 and establishes the data tunnel.

Encryption protocols: AES (Advanced Encryption Standard) is preferred. 3DES is deprecated. DES is weak. The exam expects you to recognise which are acceptable.

Integrity protocols: HMAC-SHA-256 is preferred. SHA-1 is deprecated in favour of SHA-2 or SHA-3.

Authentication methods: pre-shared keys (PSK) and digital certificates. The exam will ask which is more scalable for many sites (certificates) and which is simpler (PSK).

The difference between policy-based and route-based VPNs. Route-based using VTI is newer and more flexible.

The use of NAT traversal (NAT-T) when both VPN endpoints are behind a device performing Network Address Translation (NAT). The exam might ask what happens if NAT-T is not used.

Trap patterns to watch for:

They will give you a scenario where the tunnel is not forming and ask for the most likely cause. Common traps: mismatched pre-shared keys, mismatched encryption algorithms, firewall blocking UDP port 500, or IP addresses on the wrong subnets.

They might ask about the 'IKE lifetime'. The exam often sets a trap by making you think a longer lifetime is always better, but there is a security trade-off. The correct answer is typically a balance (e.g., 86400 seconds for Phase 1, 3600 seconds for Phase 2).

They will present 'faster' or 'simpler' options that are insecure. For example, options like 'Use DES for speed' are correct but insecure. The exam will ask you to select the best security practice.

What the exam does NOT test: deep mathematical details of encryption algorithms or advanced BGP routing over VPNs. Stick to the basics of configuration, troubleshooting, and security properties.

Key Takeaways

A site-to-site VPN connects two entire networks over a public network, using encryption to create a secure tunnel.

IPsec tunnel mode is the standard for site-to-site VPNs; it encrypts the entire original IP packet, including the header.

The Internet Key Exchange (IKE) has two phases: Phase 1 establishes a secure management channel, and Phase 2 establishes the data tunnel.

Route-based VPNs using Virtual Tunnel Interfaces (VTI) are more flexible and scalable than traditional policy-based VPNs.

Common reasons for a VPN tunnel failing include mismatched pre-shared keys, mismatched encryption algorithms, or firewall rules blocking UDP ports 500 and 4500.

Remote-access VPNs and site-to-site VPNs are distinct technologies; the first connects individual devices, the second connects entire networks.

Easy to Mix Up

These come up on the exam all the time. Here's how to tell them apart.

IPsec Tunnel Mode

Encrypts the entire original IP packet

Used for site-to-site VPNs

Adds a new IP header to the encrypted packet

IPsec Transport Mode

Encrypts only the payload of the packet

Used for host-to-host or host-to-gateway connections

Original IP header remains visible

Policy-Based VPN

Uses access lists to define interesting traffic

Less flexible; changes require modifying ACLs

Can be simpler for small, static networks

Route-Based VPN (VTI)

Uses a virtual tunnel interface and routing

More flexible; routing updates handle changes

Better for dynamic routing protocols and scaling

Pre-Shared Key (PSK)

Simpler to set up

Less scalable for many sites

Each pair of sites needs a unique key

Digital Certificate

More secure and scalable

Requires a Public Key Infrastructure (PKI)

Each device has a unique certificate issued by a Certificate Authority (CA)

Site-to-Site VPN

Connects two entire networks

Always-on connection between sites

No client software needed on user devices

Remote-Access VPN

Connects individual devices to a network

On-demand connection

Requires client software (e.g., AnyConnect) on each device

Watch Out for These

Mistake

A site-to-site VPN is the same as a remote-access VPN, just for two offices.

Correct

They are different. A remote-access VPN connects individual devices (like a laptop) to a network. A site-to-site VPN connects two entire networks so that all devices on each network can communicate as if they were local.

Beginners confuse the two because both use the term 'VPN'. The architecture and configuration are fundamentally different.

Mistake

IPsec encryption makes the connection faster than a leased line.

Correct

IPsec adds overhead; it can make the connection slightly slower due to encryption processing. Leased lines are dedicated and offer consistent latency, but VPNs are cheaper.

People assume encryption = security = efficiency = speed. Encryption adds processing time and packet overhead.

Mistake

If the internet is down, the VPN still works because it is a 'private' tunnel.

Correct

The VPN tunnel runs over the internet. If the internet connection at either office fails, the VPN tunnel is broken.

The word 'private' in VPN misleads beginners into thinking it is a separate physical network.

Mistake

Setting up a site-to-site VPN requires special software on user computers.

Correct

No software is needed on user computers. The VPN is configured on network devices (routers/firewalls) at each site, and users do not need to do anything.

Beginners associate VPNs with client software like OpenVPN or Cisco AnyConnect, which are for remote-access VPNs.

Mistake

The two sites must have public static IP addresses for the VPN to work.

Correct

While static IPs are easiest, dynamic IPs can be used with Dynamic Multipoint VPN (DMVPN) or by using a VPN concentrator that accepts connections from dynamic addresses.

Many examples in study materials use static IPs, leading beginners to believe it is the only way.

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Frequently Asked Questions

What is the difference between IPsec tunnel mode and transport mode?

In tunnel mode, the entire original IP packet (header and payload) is encrypted and placed into a new IP packet. This is used for site-to-site VPNs. In transport mode, only the payload is encrypted, leaving the original IP header visible; this is used for connections between individual devices.

Can I use a site-to-site VPN with only one public IP address?

Yes, if your router or firewall can perform NAT and use NAT traversal (NAT-T). This allows the VPN to work even if one or both gateways are behind a NAT device. You may need to configure port forwarding or allow UDP port 4500.

What is a pre-shared key (PSK) in a VPN?

A pre-shared key is a secret password shared between the two VPN gateways before the connection is established. It is used to authenticate each gateway to the other during IKE Phase 1.

Does a site-to-site VPN always use the internet?

Yes, a site-to-site VPN typically runs over the internet or another public IP network. It creates a secure tunnel through that public network. It can also run over a private MPLS network, but that is less common.

What is a Virtual Tunnel Interface (VTI)?

A Virtual Tunnel Interface (VTI) is a logical interface on a router that represents the VPN tunnel. Instead of using policy-based rules, you route traffic into the VTI just like any physical interface. This makes configuration simpler and more scalable.

What does 'Dead Peer Detection' (DPD) do?

Dead Peer Detection (DPD) is a feature that periodically checks if the other VPN gateway is still reachable. If the remote peer does not respond, DPD tears down the tunnel and attempts to re-establish it, preventing traffic from being sent into a dead connection.

Terms Worth Knowing

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