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Ultimate Guide to Site-to-Site VPN Technologies on Cisco ASA

Demand for secure communications over the internet rapidly grows daily within organizations. There’s no big surprise why. After all, CPO Magazine reported that the FBI reported about 847,376 cybersecurity complaints last year, representing almost $7 billion in business losses.

In this changing landscape, organizations are forced to implement appropriate technologies to satisfy requirements and provide a simple, secure base for exchanging data between geographically connected dispersed sites.

The simplest and best approach to these new business trends that follows modern security standards is to implement an appropriate VPN deployment based on the organization’s requirements.

Such an arrangement provides high-level protection for transferred data over high-speed broadband internet connections and virtually connects all remote corporate sites, allowing full access to all services.

In this article, we will:

  • Provide an overview and cover the basics of site-to-site VPN technology.
  • Find out more about the benefits it provides.
  • Take a look at the configuration steps for implementing a site-to-site VPN on a Cisco ASA firewall by using the ASDM management tool.

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An Overview of Site-to-Site VPN

Back in the day, organizations relied heavily on classic router WANs to interconnect geographically dispersed sites, exchange data and offer access to internal services.

Today, WANs are considered obsolete and not appropriate for modern business requirements, and have been replaced with site-to-site VPNs. This type of VPN allows secure connectivity between enterprise sites and the ability to partner networks over an untrusted public network, such as the internet.

Site-to-site IPsec VPN deployment between headquarters and a branch office

The site-to-site VPNs are usually deployed between branch offices and the headquarters, but they can also be deployed between offices from the same organization.

This VPN type integrates the IPsec framework as a mechanism for applying various security algorithms to provide confidentiality, integrity, authentication and anti-reply protection.

At the same time, the basic requirements — such as high reliability and extensive scalability — are satisfied with the site-to-site VPN deployments and achieved more cost-effectively. On top of that, this VPN type provides more scalable performance and greater flexibility.

Because of the support for various topologies and technologies, the IPsec VPNs can be deployed in many different variants. Ensure you are familiar with all of those options to choose and apply the most appropriate one when designing an IPsec site-to-site VPN solution.

Site-to-Site VPN Topologies

A network topology represents how certain entities are interconnected with each other over a public or private network. The same approach applies to VPNs as well.

Geographically dispersed sites are connected to the headquarters or between each other over the internet, which defines the VPN topology, which generally means a logical one.

Support for hub-and-spoke, point-to-point and full mesh VPN topologies

Even though numerous logical VPN topologies can be used in site-to-site VPNs, three of them are most commonly used in deployments. They are:

  • Point-to-point VPN: A direct VPN tunnel between two sites that need to connect securely. Some networks may consist of several individual point-to-point VPN connections when enterprise requirements demand it.

  • Hub-and-spoke: This is the most commonly deployed topology in general. The way this topology functions is quite simple. There is one central site that represents the hub, and the rest of the sites (also called spokes) exclusively connect with the hub. In a real case scenario, the headquarters represents the hub, while the branch offices are the spokes.

    Typically, most of the traffic that is exchanged between the spokes goes through the hub, however, direct communication between spokes is also possible. This is supported in Cisco Dynamic Multipoint VPN, or DMVPN, in which case the hub acts as a relay and facilitates the spoke-to-spoke communication.

  • Full mesh: Probably the best yet the most expensive and complex solution. With this topology, each site is connected to every other site, which results in a fully-meshed network. This provides any-to-any communication, the most optimal paths in the network, and the greatest flexibility.

Besides the three main VPN topologies that are commonly used, three additional more complex topologies can be used in site-to-site VPN deployments when there are special requirements. These VPN topologies are:

  • Partial mesh, which acts as a light version of the full mesh topology.

  • Tiered hub-and-spoke, where a single device can function as a hub for one part of the topology and spoke for the other.

  • Joined hub-and-spoke, where two topologies such as point-to-point, hub-and-spoke or full mesh form a point-to-point tunnel when connecting to each other.


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Site-to-Site VPN Deployment Types You Need to Know

Even though we will focus on configuring a simple site-to-site (point-to-point) VPN later on in the article, you should be aware that there are a few additional site-to-site VPN deployments that you can implement:

  • Basic P2P: Solution that provides a point-to-point connection between two locations that need to connect, such as a headquarters and a branch office.

  • DMVPN: Cisco solution that allows scalable IPsec VPN, supporting hub-and-spoke and spoke-to-spoke VPN tunnels for greater flexibility, lower bandwidth consumption, and simpler implementation and management.

  • FlexVPN: Cisco solution that greatly simplifies the overall VPN implementation when organization requirements demand several VPN types deployed at the same time.

  • GET VPN: Tunnel-less solution suitable for deployment in MPLS networks that efficiently secures IP unicast and multicast traffic. This VPN type combines IPsec with Group Domain of Interpretation (GDOI) to provide any-to-any connectivity.

Understanding the Site-to-Site Tunnel Negotiation Process

Before we start with the site-to-site VPN implementation on a Cisco ASA firewall, we first need to take a look at the site-to-site VPN tunnel negotiation process.

This is essential to easily understand the IPsec site-to-site VPN configuration steps used later on in the article, but most importantly the overall configuration process.

Overview of the site-to-site tunnel negotiation process between two Cisco ASA firewalls

The tunnel negotiation process is quite simple and involves several steps, so let’s take a look at the figure above and find out what those steps are. The main requirement in our use case is for firewalls ASA1 and ASA2 to establish a VPN tunnel so PC1 and PC2 can securely exchange data with each other over the internet.

For the VPN to get established, PC1 must send some data (also known as “interesting traffic”) to PC2 to trigger the negotiation process between the firewalls. The process consists of two phases, and each phase is responsible for building different tunnels.

In Phase 1, ASA1 and ASA2 negotiate security parameters among executing other things to build a secure tunnel. In other words, they need to find common support for cryptographic algorithms that will be used for encryption, authentication, and integrity to protect the data that will be sent through the VPN.

Upon agreement, they build something called ISAKMP Security Association (SA), which represents a bi-directional secure tunnel, through which Phase 2 takes place.

Then, in Phase 2, both firewalls continue with the VPN establishment process and they negotiate security parameters one more time. This step is needed to create the “real” VPN tunnel that will be used to protect the data exchanged between PC1 and PC2.

Keep in mind that the whole communication of Phase 2 is now secured because it goes through the tunnel established in Phase 1. Now, ASA1 uses the active ISAKMP SA to initiate negotiation of an IPsec SA to ASA2, which is the goal of the negotiation process in the first place.

This IPsec SA is a unidirectional tunnel whose responsibility is to protect the real data exchanged from the sender to the receiver. Since Phase 2 IPsec ESP SAs are unidirectional, ASA2 must also negotiate an additional IPsec SA towards ASA1.

To summarize, the result of the negotiation process is to establish a tunnel within a tunnel. The ISAKMP SA is the outer tunnel and is needed to protect the negotiation of the IPsec SAs, while the IPsec SAs represent the inner tunnels and protect the exchanged data. When the existing IPsec SAs expire, they are replaced with new IPsec SAs, negotiated using the ISAKMP SA.

Configuring a Site-to-Site VPN on a Cisco ASA

Configuring a site-to-site VPN on a Cisco ASA firewall is no different than configuring it on a Cisco router or Cisco Firepower NGFW firewall. In our use case in the figure below, we will see how it can be deployed on a Cisco ASA in the branch office, so it can establish a VPN to the Cisco ASA in the Headquarters.

This would allow a secure transfer of data between the finance network in the branch office to the finance servers, located behind the ASA firewall at the headquarters.

A topology representation of Cisco ASA firewalls included in a site-to-site IPsec VPN deployment

Recommendation for Pre-deployment

It is very important to have the following information ready before starting with the deployment:

  • Peer IP addresses: These are the public IP addresses that both devices will use on the internet. In our case, the branch ASA uses, while the headquarters ASA has the IP address of

  • Local and remote networks: These are the protected networks. In other words, data going out of these networks will be sent through the VPN tunnel.

  • PSK: Peers must have the same pre-shared key to authenticate successfully with each other. However, keep in mind that this authentication solution is not scalable and is suitable for small networks in general. For greater scalability, a preferred authentication method is to use digital certificates.

  • ISAKMP policy: A matching policy between the peers must exist for Phase 1 to finish successfully. The matching criteria are encryption, authentication, hashing, Diffie-Hellman Group, and lifetime.

  • Transform set: A matching transform set defines how the exchanged data will be protected. It is recommended to use at least AES-128bit for encryption and SHA-256 for hashing.

Configuration Steps on a Cisco ASDM for Implementing Site-to-Site VPN

Configuring a site-to-site VPN on a Cisco ASA firewall can be done in two different ways. The first approach is by using the CLI (which is the more difficult option because you must know the exact commands) while the other is to use the Adaptive Security Device Manager (ASDM) management tool, which allows the Cisco ASA to be managed through a graphical user interface.

However, if the ASDM is selected for configuring the VPN, there are not one but three different approaches that can be used. The first two options rely on a manual configuration and you can use the advanced menus or the connection profiles menus, which most of the time is the preferred method.

The last one offers an automated procedure to get the same result in a much easier way by using the site-to-site VPN wizard. In our use case, we will use this automated option, so let’s go step by step and take a look at how simple the configuration process is.

Starting the site-to-site VPN wizard on a Cisco ASA firewall

As you can notice, there are multiple VPN wizards available to choose from, however, we will choose the site-to-site VPN wizard.

Introduction of the site-to-site VPN wizard on a Cisco ASA firewall

The first step (introduction) after you start the site-to-site VPN wizard provides optional guidance on how to use the wizard, however, we will skip that part and go “next.”

Peer device identification step of the site-to-site VPN wizard on a Cisco ASA firewall

The second step is the start of the site-to-site VPN configuration. It requires providing the peer IP address and the local exit interface that will be used to connect to the peer.

In our case, the IP address of the peer device (headquarters ASA) is and the local interface that will be used on the branch ASA is “outside.” Keep in mind that when using Cisco ASA, the interfaces are represented by names.

Step of the site-to-site VPN wizard on a Cisco ASA firewall for defining traffic to protect

In the third step, we need to define the local and remote networks that will be protected by the IPsec VPN. In our case, the local network behind the branch ASA is the Finance network (an object that represents the IP network), while the remote network behind the headquarters ASA is, where the finance servers belong.

Step of the site-to-site VPN wizard on a Cisco ASA firewall for defining security

The fourth step is about defining the authentication method. In our case, we will choose a simple configuration, therefore the correct pre-shared key must be applied.

Step of the site-to-site VPN wizard on a Cisco ASA firewall for configuring NAT exemption

The last step is all about network address translation (NAT). If it is required, here you can exempt local hosts or networks from NAT.

Final step of the site-to-site VPN wizard on a Cisco ASA firewall

When we finish with the configuration steps, a summary of the configuration is displayed. It contains all data that has been defined during the configuration steps and the cryptographic algorithms that are supported and can be used in the VPN deployment.

Preview of the CLI commands configured during the site-to-site VPN wizard on a Cisco ASA firewall

The last part provides a preview of the CLI commands that will be sent to the Cisco ASA.

As you can notice from the configuration example above, using the wizard is not a difficult process at all, and in just a few steps you can easily set up your Cisco ASA firewall with a VPN tunnel to the peer device on the other side.

A Look Ahead

Once the site-to-site VPN is successfully established, the Cisco ASA and the peer on the other side can securely exchange data without any risk of eavesdropping or man-in-the-middle attacks.

By following these helpful tips, you’ll understand the basics of utilizing site-to-site VPN technology — the best way to capitalize on evolving trends and for your organization, providing protection for transferred data and equipping you to worry about more important things.

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