Configuring An Ipsec Tunnel
IPSec can be configured in tunnel mode or transport mode. IPSec tunnel mode can be used as an alternative to a GRE tunnel, or in conjunction with a GRE tunnel. In IPSec tunnel mode, the entire original IP datagram is encrypted, and it becomes the payload in a new IP packet. This mode allows a network device, such as a router, to act as an IPSec proxy. That is, the router performs encryption on behalf of the hosts. The source router encrypts packets and forwards them along the IPSec tunnel. The destination router decrypts the original IP datagram and forwards it on to the destination system. Tunnel mode protects against traffic analysis with tunnel mode, an attacker can only determine the tunnel endpoints and not the true source and destination of the packets passing through the tunnel, even if they are the same as the tunnel endpoints.
Note IPSec tunnel mode configuration instructions are described in detail in the .
Figure 3-6 IPSec in Tunnel and Transport Modes
Special Notice: Licensing Structure
You need to purchase client license from a partner like CDW or through your company’s device procurement. There are options for 1 user or packets of licenses including one year for 25 users . Other license options available as well, including perpetual licenses. For more details on licensing, check out the links in the Licensing Information section below.
For additional information on AnyConnect licensing on the RV340 series routers, check out the article AnyConnect Licensing for the RV340 Series Routers.
Create The VPN Gateway
In this step, you create the virtual network gateway for your VNet. Creating a gateway can often take 45 minutes or more, depending on the selected gateway SKU.
Note
The Basic gateway SKU does not support IKEv2 or RADIUS authentication. If you plan on having Mac clients connect to your virtual network, do not use the Basic SKU.
The virtual network gateway uses specific subnet called the gateway subnet. The gateway subnet is part of the virtual network IP address range that you specify when configuring your virtual network. It contains the IP addresses that the virtual network gateway resources and services use.
When you create the gateway subnet, you specify the number of IP addresses that the subnet contains. The number of IP addresses needed depends on the VPN gateway configuration that you want to create. Some configurations require more IP addresses than others. We recommend that you create a gateway subnet that uses a /27 or /28.
In Search resources, services, and docs type virtual network gateway. Locate Virtual network gateway in the Marketplace search results and select it to open the Create virtual network gateway page.
On the Basics tab, fill in the values for Project details and Instance details.
Important
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How To Set Up Openvpn Access Server For Site
We are assuming that you already have an OpenVPN Access Server installation working, and that it is installed in your private network behind a router with Internet access and has a private IP address, with port forwarding set up so that it can be reached from the outside, and with appropriate settings made so that it is actually reachable with an OpenVPN client program from the outside. In other words, that you have an OpenVPN Access Server installation that works and lets OpenVPN clients connect. If you haven’t installed Access Server yet then please do so first. See the Access Server installation options page for more information.
This section here describes which settings to configure in the OpenVPN Access Server to make a site-to-site setup possible. We are going to assume we’re setting up the site-to-site setup as shown in the pictures above, with the subnets used there. If your subnets are different, and they very likely are, you should adjust as needed to match your situation. Important note: it is required for site-to-site to work that the subnets are different in the two networks.
- Network 172.16.0.0 with subnet mask 255.255.240.0 through gateway 192.168.70.222
- Network 10.0.60.0 with subnet mask 255.255.255.0 through gateway 192.168.70.222
Create A Customer Gateway

A customer gateway provides information to AWS about your customer gateway device or software application. For more information, see Customer gateway.
If you plan to use a private certificate to authenticate your VPN, create a private certificate from a subordinate CA using AWS Certificate Manager Private Certificate Authority. For information about creating a private certificate, see Creating and managing a private CA in the AWS Certificate Manager Private Certificate Authority User Guide.
You must specify either an IP address, or the Amazon Resource Name of the private certificate.
To create a customer gateway using the console
Open the Amazon VPC console at.
In the navigation pane, choose Customer gateways, and then Create customer gateway.
Complete the following and then choose Create customer gateway:
For Name tag, enter a name for your customer gateway. Doing so creates a tag with a key of Name and the value that you specify.
For BGP ASN, enter a Border Gateway Protocol Autonomous System Number for your customer gateway.
For IP address, enter the static, internet-routable IP address for your customer gateway device. If your customer gateway device is behind a NAT device that’s enabled for NAT-T, use the public IP address of the NAT device.
If you want to use a private certificate, forCertificate ARN, choose the Amazon Resource Name of the private certificate.
For Device, enter a name for the device that hosts this customer gateway.
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What Is A VPN
A Virtual Private Network allows to route network traffic over a public network in a private and secure way. In fact, a VPN uses a private tunnel connection enabling traffic flow between your local network and another network.
There are three main use cases for using a VPN:
- Corporate environment: a VPN is used to access a corporate network from a branch office, at a lower cost than a dedicated line.
- Privacy and anonymity: a VPN lets you mask your current IP address and location, using encryption to keep the connection confidential.
- Connecting data centres: a VPN is used to connect two different data centres or cloud regions.
In this tutorial we are going to focus on the first use case. In particular, Im going to explain how to set up a VPN connection between a local network and resources deployed in a VPC within the AWS network. In AWS jargon this is referred to as an AWS Site-to-Site VPN. The diagram below shows what we are going to build.
Note that this tutorial uses a computer running Linux as the customer gateway.
Create A Virtual Network
When you create a virtual network to use for a S2S connection, you need to make sure that the address spaces that you specify do not overlap with any of the client address spaces for the local sites that you want to connect to. If you have overlapping subnets, your connection won’t work properly.
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If you already have a VNet, verify that the settings are compatible with your VPN gateway design. Pay particular attention to any subnets that may overlap with other networks.
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If you don’t already have a virtual network, create one. Screenshots are provided as examples. Be sure to replace the values with your own.
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To Add Or Remove Trusted Root Certificates
You can add and remove trusted root certificates from Azure. When you remove a root certificate, clients that have a certificate generated from that root won’t be able to authenticate, and thus will not be able to connect. If you want a client to authenticate and connect, you need to install a new client certificate generated from a root certificate that is trusted to Azure.
You can add up to 20 trusted root certificate .cer files to Azure. For instructions, see the section Upload a trusted root certificate.
To remove a trusted root certificate:
Create A Local Network Gateway
The local network gateway is a specific object that represents your on-premises location for routing purposes. You give the site a name by which Azure can refer to it, then specify the IP address of the on-premises VPN device to which you’ll create a connection. You also specify the IP address prefixes that will be routed through the VPN gateway to the VPN device. The address prefixes you specify are the prefixes located on your on-premises network. If your on-premises network changes or you need to change the public IP address for the VPN device, you can easily update the values later.
Create a local network gateway using the following values:
- Name: Site1
- Resource Group: TestRG1
- Location: East US
From the Azure portal, in Search resources, services, and docs type local network gateway. Locate local network gateway under in the search results and select it. This opens the Create local network gateway page.
On the Create local network gateway page, specify the values for your local network gateway.
Note
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Why Turning Off Implied Rules Blocks Firewall Control Connections
If you turn off implicit rules, you may not be able to install an Access Control Policy on a remote Security Gateway. Even if you configure explicit rules rather than implied rules, you may still not be able to install the policy:
To configure a VPN between Security Gateways A and B through SmartConsole, the administrator must install a Policy from the Security Management Server to the Security Gateways.
The Security Management Server successfully installs the Policy on Security Gateway A. Security Gateway A recognizes that Security Gateways A and B now belong to the same VPN Community. However, Security Gateway B does not yet have the Policy.
The Security Management Server opens a connection to Security Gateway B to install the Policy.
Security Gateway A allows the connection because of the explicit rules that allow the control connections. Security Gateway A starts IKE negotiation with Security Gateway B to build a VPN tunnel for the control connection.
Security Gateway B cannot negotiate with Security Gateway A because it does not yet have the Policy. Therefore, Policy installation on Security Gateway B fails.
Make sure that control connections do not have to pass through a VPN tunnel.
By Step Description Of How Traffic Flows
We have created a series of pictures that show how a request from a client computer in the subsidiary office reaches an application server at the headquarter office, and how a response gets sent back. Each step of the process is shown clearly with highlighted lines and relevant network information. Simply go through the images to see a step by step progression. It’s worth noting that this type of setup still allows other VPN clients to log on to the OpenVPN Access Server and gain access to any of the devices in these 2 networks. Also, a site-to-site setup need not be limited to one subsidiary network, it can be multiple just as easily.
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To Connect From A Mac VPN Client
From the Network dialog box, locate the client profile that you want to use, specify the settings from the VPNSettings.xml, and then select Connect. For detailed instructions, see Generate and install VPN client configuration files – macOS.
If you are having trouble connecting, verify that the virtual network gateway is not using a Basic SKU. The Basic SKU is not supported for Mac clients.
What It Looks Like

Site-to-site VPNs are intended to connect entire networks, usually from different locations. They work by routing traffic between two site-to-site VPN tunnels.
For example, an organization which has offices in Los Angeles, Chicago, and New York can utilize a site-to-site VPN to connect all the offices together and secure site-to-site connectivity between all of them.
This, in effect, creates one whole network , where users can exchange data and information with each other from completely different placesall encrypted and secured by the VPN.
For users, there is virtually no difference in their daily working functions.
Since site-to-site VPNs encrypt data at a gateway, users dont have to have any of the VPN software installed on their computerso long as theyre connected to the site , their data is protected.
This is in contrast to a remote access VPN.
If you use a VPN at home, a remote access VPN is almost certainly what it is.
It requires you to launch the application , sign in, and keep it running for as long as you want to use it.
So, with a site-to-site VPN, youre sparing staff in the IT department the chore of having to individually install software on every device that needs protection.
An extranet site-to-site works in much the same way in that employees wont see the VPN or have to run any applicationsjust with the difference being only certain information is shared between the sites.
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Configure Settings For VPN Clients
To connect to the virtual network gateway using P2S, each computer uses the VPN client that is natively installed as a part of the operating system. For example, when you go to VPN settings on your Windows computer, you can add VPN connections without installing a separate VPN client. You configure each VPN client by using a client configuration package. The client configuration package contains settings that are specific to the VPN gateway that you created.
For steps to generate and install VPN client configuration files, see Create and install VPN client configuration files for Azure certificate authentication P2S configurations.
There Are Different Types Of VPN
Yes, and they each serve distinct purposes designed to be implemented based on a companys needs.
VPNs can be split up into three categories:
- Remote access VPNs: Typically consumer-grade VPNs, and what individuals will be accustomed to. Examples include NordVPN and ExpressVPN
- Intranet-based site-to-site: Multiple connected LANs that collectively make up a wide area network useful for securely pooling resources across a company with more than one office
- Extranet-based site-to-site: Commonly used between companies that are partners, allowing them to share specified information externally while still maintaining security and allowing internal networks to be used only by internal workers
Today, well be looking at site-to-site VPNs, and the benefits they can bring to SMBs going forward.
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Additional Configuration Required For Ike Policies
Depending on which authentication method you specify in your IKE policies, you need to complete an additional companion configuration before IKE and IPSec can successfully use the IKE policies.
Each authentication method requires an additional companion configuration as follows:
RSA signatures method:
If you specify RSA signatures as the authentication method in a policy, you must configure the peers to obtain certificates from a certification authority . Configure this certificate support as described in the “Configuring Certification Authority Interoperability” chapter of the Cisco IOS Security Configuration Guide.
The certificates are used by each peer to securely exchange public keys. When both peers have valid certificates, they will automatically exchange public keys with each other as part of any IKE negotiation in which RSA signatures are used.
RSA encrypted nonces method:
If you specify RSA encrypted nonces as the authentication method in a policy, you need to ensure that each peer has the other peers’ public keys.
Unlike RSA signatures, the RSA encrypted nonces method does not use certificates to exchange public keys. Instead, you ensure that each peer has the others’ public keys by doing the following:
Manually configure RSA keys as described in the “Configuring Internet Key Exchange Security Protocol” chapter of the Cisco IOS Security Configuration Guide.
Ensure that an IKE exchange using RSA signatures has already occurred between the peers.
Basic Site To Site VPN Configuration
It is more complex to configure VPN with external Security Gateways than to configure VPN with internal Security Gateways because:
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There are two systems to configure separately.
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Administrators of the peer VPN Security Gateways must coordinate with each other and agree on all details. The administrators must manually supply details such as the IP address and the VPN domain topology. These details cannot be detected automatically.
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Allowing Firewall Control Connections Inside A VPN
If you turn off implied rules, make sure that control connections are not changed by the Security Gateways. Add the services that are used for control connections to the Excluded Services page of the Community object. See sk42815 for details.
Note – Although control connections between the Security Management Server and the Security Gateway are not encrypted by the community, they are still encrypted and authenticated with Secure Internal Communication .
To Connect To A Virtual Machine
These instructions apply to Windows clients.
You can connect to a VM that is deployed to your VNet by creating a Remote Desktop Connection to your VM. The best way to initially verify that you can connect to your VM is to connect by using its private IP address, rather than computer name. That way, you’re testing to see if you can connect, not whether name resolution is configured properly.
Locate the private IP address. You can find the private IP address of a VM by either looking at the properties for the VM in the Azure portal, or by using PowerShell.
Azure portal – Locate your virtual machine in the Azure portal. View the properties for the VM. The private IP address is listed.
PowerShell – Use the example to view a list of VMs and private IP addresses from your resource groups. You don’t need to modify this example before using it.
$VMs = Get-AzVM$Nics = Get-AzNetworkInterface | Where VirtualMachine -ne $nullforeach
Verify that you’re connected to your VNet.
Open Remote Desktop Connection by typing “RDP” or “Remote Desktop Connection” in the search box on the taskbar, then select Remote Desktop Connection. You can also open Remote Desktop Connection using the ‘mstsc’ command in PowerShell.
In Remote Desktop Connection, enter the private IP address of the VM. You can select “Show Options” to adjust additional settings, then connect.
Troubleshoot a connection
If you’re having trouble connecting to a virtual machine over your VPN connection, check the following:
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