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-->This article helps you securely connect individual clients running Windows, Linux, or macOS to an Azure VNet. Point-to-site VPN connections are useful when you want to connect to your VNet from a remote location, such when you are telecommuting from home or a conference. You can also use P2S instead of a Site-to-Site VPN when you have only a few clients that need to connect to a VNet. Point-to-site connections do not require a VPN device or a public-facing IP address. P2S creates the VPN connection over either SSTP (Secure Socket Tunneling Protocol), or IKEv2.
For more information about point-to-site VPN, see About point-to-site VPN. To create this configuration using the Azure portal, see Configure a point-to-site VPN using the Azure portal.
Point-to-site native Azure certificate authentication connections use the following items, which you configure in this exercise:
- A RouteBased VPN gateway.
- The public key (.cer file) for a root certificate, which is uploaded to Azure. Once the certificate is uploaded, it is considered a trusted certificate and is used for authentication.
- A client certificate that is generated from the root certificate. The client certificate installed on each client computer that will connect to the VNet. This certificate is used for client authentication.
- VPN client configuration. The VPN client is configured using VPN client configuration files. These files contain the necessary information for the client to connect to the VNet. The files configure the existing VPN client that is native to the operating system. Each client that connects must be configured using the settings in the configuration files.
Prerequisites
Verify that you have an Azure subscription. If you don't already have an Azure subscription, you can activate your MSDN subscriber benefits or sign up for a free account.
Azure PowerShell
Important
Many of the steps in this article can use the Azure Cloud Shell. However, you can't use Cloud Shell to generate certificates. Additionally, to upload the root certificate public key, you must either use Azure PowerShell locally, or the Azure portal.
This article uses PowerShell cmdlets. To run the cmdlets, you can use Azure Cloud Shell. The Azure Cloud Shell is a free interactive shell that you can use to run the steps in this article. It has common Azure tools preinstalled and configured to use with your account.
To open the Cloud Shell, just select Try it from the upper right corner of a code block. You can also launch Cloud Shell in a separate browser tab by going to https://shell.azure.com/powershell. Select Copy to copy the blocks of code, paste it into the Cloud Shell, and press enter to run it.
You can also install and run the Azure PowerShell cmdlets locally on your computer. PowerShell cmdlets are updated frequently. If you have not installed the latest version, the values specified in the instructions may fail. To find the versions of Azure PowerShell installed on your computer, use the Get-Module -ListAvailable Az cmdlet. To install or update, see Install the Azure PowerShell module.
1. Sign in
If you are running PowerShell locally, open the PowerShell console with elevated privileges and connect to your Azure account. The Connect-AzAccount cmdlet prompts you for credentials. After authenticating, it downloads your account settings so that they are available to Azure PowerShell.
If you are using Azure Cloud Shell instead of running PowerShell locally, you will notice that you don't need to run Connect-AzAccount. Azure Cloud Shell connects to your Azure account automatically after you select Try It.
If you are running PowerShell locally, sign in.
If you have more than one subscription, get a list of your Azure subscriptions.
Specify the subscription that you want to use.
2. Declare variables
We use variables for this article so that you can easily change the values to apply to your own environment without having to change the examples themselves. Declare the variables that you want to use. You can use the following sample, substituting the values for your own when necessary. If you close your PowerShell/Cloud Shell session at any point during the exercise, just copy and paste the values again to re-declare the variables.
3. Configure a VNet
Create a resource group.
Create the subnet configurations for the virtual network, naming them FrontEnd and GatewaySubnet. These prefixes must be part of the VNet address space that you declared.
Create the virtual network.
In this example, the -DnsServer server parameter is optional. Specifying a value does not create a new DNS server. The DNS server IP address that you specify should be a DNS server that can resolve the names for the resources you are connecting to from your VNet. This example uses a private IP address, but it is likely that this is not the IP address of your DNS server. Be sure to use your own values. The value you specify is used by the resources that you deploy to the VNet, not by the P2S connection or the VPN client.
Specify the variables for the virtual network you created.
A VPN gateway must have a Public IP address. You first request the IP address resource, and then refer to it when creating your virtual network gateway. The IP address is dynamically assigned to the resource when the VPN gateway is created. VPN Gateway currently only supports Dynamic Public IP address allocation. You cannot request a Static Public IP address assignment. However, it doesn't mean that the IP address changes after it has been assigned to your VPN gateway. The only time the Public IP address changes is when the gateway is deleted and re-created. It doesn't change across resizing, resetting, or other internal maintenance/upgrades of your VPN gateway.
Request a dynamically assigned public IP address.
4. Create the VPN gateway
In this step, you configure and create the virtual network gateway for your VNet.
- The -GatewayType must be Vpn and the -VpnType must be RouteBased.
- The -VpnClientProtocol is used to specify the types of tunnels that you would like to enable. The tunnel options are OpenVPN, SSTP, and IKEv2. You can choose to enable one of them or any supported combination. If you want to enable multiple types, then specify the names separated by a comma. OpenVPN and SSTP cannot be enabled together. The strongSwan client on Android and Linux and the native IKEv2 VPN client on iOS and OSX will use only the IKEv2 tunnel to connect. Windows clients try IKEv2 first and if that doesn’t connect, they fall back to SSTP. You can use the OpenVPN client to connect to OpenVPN tunnel type.
- The virtual network gateway 'Basic' SKU does not support IKEv2, OpenVPN or RADIUS authentication. If you are planning on having Mac clients connect to your virtual network, do not use the Basic SKU.
- A VPN gateway can take up to 45 minutes to complete, depending on the gateway sku you select. This example uses IKEv2.
Configure and create the virtual network gateway for your VNet. It takes approximately 45 minutes for the gateway to create.
Once your gateway is created, you can view it using the following example. If you closed PowerShell or it timed out while your gateway was being created, you can declare your variables again.
5. Add the VPN client address pool
After the VPN gateway finishes creating, you can add the VPN client address pool. The VPN client address pool is the range from which the VPN clients receive an IP address when connecting. Use a private IP address range that does not overlap with the on-premises location that you connect from, or with the VNet that you want to connect to.
In this example, the VPN client address pool is declared as a variable in an earlier step.
6. Generate certificates
Important
You can't generate certificates using Azure Cloud Shell. You must use one of the methods outlined in this section. If you want to use PowerShell, you must install it locally.
Certificates are used by Azure to authenticate VPN clients for point-to-site VPNs. You upload the public key information of the root certificate to Azure. The public key is then considered 'trusted'. Client certificates must be generated from the trusted root certificate, and then installed on each client computer in the Certificates-Current User/Personal certificate store. The certificate is used to authenticate the client when it initiates a connection to the VNet.
If you use self-signed certificates, they must be created using specific parameters. You can create a self-signed certificate using the instructions for PowerShell and Windows 10, or, if you don't have Windows 10, you can use MakeCert. It's important that you follow the steps in the instructions when generating self-signed root certificates and client certificates. Otherwise, the certificates you generate will not be compatible with P2S connections and you receive a connection error.
Root certificate
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Obtain the .cer file for the root certificate. You can use either a root certificate that was generated with an enterprise solution (recommended), or generate a self-signed certificate. After you create the root certificate, export the public certificate data (not the private key) as a Base64 encoded X.509 .cer file. You upload this file later to Azure.
Enterprise certificate: If you're using an enterprise solution, you can use your existing certificate chain. Acquire the .cer file for the root certificate that you want to use.
Self-signed root certificate: If you aren't using an enterprise certificate solution, create a self-signed root certificate. Otherwise, the certificates you create won't be compatible with your P2S connections and clients will receive a connection error when they try to connect. You can use Azure PowerShell, MakeCert, or OpenSSL. The steps in the following articles describe how to generate a compatible self-signed root certificate:
- Windows 10 PowerShell instructions: These instructions require Windows 10 and PowerShell to generate certificates. Client certificates that are generated from the root certificate can be installed on any supported P2S client.
- MakeCert instructions: Use MakeCert if you don't have access to a Windows 10 computer to use to generate certificates. Although MakeCert is deprecated, you can still use it to generate certificates. Client certificates that you generate from the root certificate can be installed on any supported P2S client.
- Linux instructions.
After you create the root certificate, export the public certificate data (not the private key) as a Base64 encoded X.509 .cer file.
Client certificate
Each client computer that you connect to a VNet with a Point-to-Site connection must have a client certificate installed. You generate it from the root certificate and install it on each client computer. If you don't install a valid client certificate, authentication will fail when the client tries to connect to the VNet.
You can either generate a unique certificate for each client, or you can use the same certificate for multiple clients. The advantage to generating unique client certificates is the ability to revoke a single certificate. Otherwise, if multiple clients use the same client certificate to authenticate and you revoke it, you'll need to generate and install new certificates for every client that uses that certificate.
You can generate client certificates by using the following methods:
Enterprise certificate:
If you're using an enterprise certificate solution, generate a client certificate with the common name value format name@yourdomain.com. Use this format instead of the domain nameusername format.
Make sure the client certificate is based on a user certificate template that has Client Authentication listed as the first item in the user list. Check the certificate by double-clicking it and viewing Enhanced Key Usage in the Details tab.
Self-signed root certificate: Follow the steps in one of the following P2S certificate articles so that the client certificates you create will be compatible with your P2S connections.
When you generate a client certificate from a self-signed root certificate, it's automatically installed on the computer that you used to generate it. If you want to install a client certificate on another client computer, export it as a .pfx file, along with the entire certificate chain. Doing so will create a .pfx file that contains the root certificate information required for the client to authenticate.
The steps in these articles generate a compatible client certificate, which you can then export and distribute.
Windows 10 PowerShell instructions: These instructions require Windows 10 and PowerShell to generate certificates. The generated certificates can be installed on any supported P2S client.
MakeCert instructions: Use MakeCert if you don't have access to a Windows 10 computer for generating certificates. Although MakeCert is deprecated, you can still use it to generate certificates. You can install the generated certificates on any supported P2S client.
Linux instructions.
After you create client certificate, export it. The client certificate will be distributed to the client computers that will connect.
7. Upload the root certificate public key information
Verify that your VPN gateway has finished creating. Once it has completed, you can upload the .cer file (which contains the public key information) for a trusted root certificate to Azure. Once a.cer file is uploaded, Azure can use it to authenticate clients that have installed a client certificate generated from the trusted root certificate. You can upload additional trusted root certificate files - up to a total of 20 - later, if needed.
Note
You can't upload the .cer file using Azure Cloud Shell. You can either use PowerShell locally on your computer, or you can use the Azure portal steps.
Declare the variable for your certificate name, replacing the value with your own.
Replace the file path with your own, and then run the cmdlets.
Upload the public key information to Azure. Once the certificate information is uploaded, Azure considers it to be a trusted root certificate. When uploading, make sure you are running PowerShell locally on your computer, or instead, you can use the Azure portal steps. You can't upload using Azure Cloud Shell.
8. Install an exported client certificate
The following steps help you install on a Windows client. For additional clients and more information, see Install a client certificate.
If you want to create a P2S connection from a client computer other than the one you used to generate the client certificates, you need to install a client certificate. When installing a client certificate, you need the password that was created when the client certificate was exported.
- Locate and copy the .pfx file to the client computer. On the client computer, double-click the .pfx file to install. Leave the Store Location as Current User, and then select Next.
- On the File to import page, don't make any changes. Select Next.
- On the Private key protection page, input the password for the certificate, or verify that the security principal is correct, then select Next.
- On the Certificate Store page, leave the default location, and then select Next.
- Select Finish. On the Security Warning for the certificate installation, select Yes. You can comfortably select 'Yes' for this security warning because you generated the certificate.
- The certificate is now successfully imported.
Make sure the client certificate was exported as a .pfx along with the entire certificate chain (which is the default). Otherwise, the root certificate information isn't present on the client computer and the client won't be able to authenticate properly.
9. Configure the VPN client
In this section, you configure the native client for your computer to connect to the virtual network gateway. For example, when you go to VPN settings on your Windows computer, you can add VPN connections. A point-to-site connection requires specific configuration settings. These steps help you create a package with the specific settings your native VPN client needs to be able connect to the virtual network over a point-to-site connection.
You can use the following quick examples to generate and install the client configuration package. For more information about package contents and additional instructions about to generate and install VPN client configuration files, see Create and install VPN client configuration files.
If you need to declare your variables again, you can find them here.
To generate configuration files
To install the client configuration package
You can use the same VPN client configuration package on each Windows client computer, as long as the version matches the architecture for the client. For the list of client operating systems that are supported, see the Point-to-Site section of the VPN Gateway FAQ.
Note
You must have Administrator rights on the Windows client computer from which you want to connect.
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Use the following steps to configure the native Windows VPN client for certificate authentication:
- Select the VPN client configuration files that correspond to the architecture of the Windows computer. For a 64-bit processor architecture, choose the 'VpnClientSetupAmd64' installer package. For a 32-bit processor architecture, choose the 'VpnClientSetupX86' installer package.
- Double-click the package to install it. If you see a SmartScreen popup, click More info, then Run anyway.
- On the client computer, navigate to Network Settings and click VPN. The VPN connection shows the name of the virtual network that it connects to.
- Before you attempt to connect, verify that you have installed a client certificate on the client computer. A client certificate is required for authentication when using the native Azure certificate authentication type.
10. Connect to Azure
Windows VPN client
Note
You must have Administrator rights on the Windows client computer from which you are connecting.
To connect to your VNet, on the client computer, navigate to VPN settings and locate the VPN connection that you created. It's named the same name as your virtual network. Select Connect. A pop-up message may appear that refers to using the certificate. Select Continue to use elevated privileges.
On the Connection status page, select Connect to start the connection. If you see a Select Certificate screen, verify that the client certificate showing is the one that you want to use to connect. If it is not, use the drop-down arrow to select the correct certificate, and then select OK.
Your connection is established.
If you have trouble connecting, check the following items:
If you exported a client certificate with Certificate Export Wizard, make sure that you exported it as a .pfx file and selected Include all certificates in the certification path if possible. When you export it with this value, the root certificate information is also exported. After you install the certificate on the client computer, the root certificate in the .pfx file is also installed. To verify that the root certificate is installed, open Manage user certificates and select Trusted Root Certification AuthoritiesCertificates. Verify that the root certificate is listed, which must be present for authentication to work.
If you used a certificate that was issued by an Enterprise CA solution and you can't authenticate, verify the authentication order on the client certificate. Check the authentication list order by double-clicking the client certificate, selecting the Details tab, and then selecting Enhanced Key Usage. Make sure Client Authentication is the first item in the list. If it isn't, issue a client certificate based on the user template that has Client Authentication as the first item in the list.
For additional P2S troubleshooting information, see Troubleshoot P2S connections.
Mac VPN client
From the Network dialog box, locate the client profile that you want to use, then click Connect.Check Install - Mac (OS X) for detailed instructions. If you are having trouble connecting, verify that the virtual network gateway is not using a Basic SKU. Basic SKU is not supported for Mac clients.
To verify a connection
These instructions apply to Windows clients.
To verify that your VPN connection is active, open an elevated command prompt, and run ipconfig/all.
View the results. Notice that the IP address you received is one of the addresses within the point-to-site VPN Client Address Pool that you specified in your configuration. The results are similar to this example:
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 are 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.
Verify that you are connected to your VNet using the Point-to-Site VPN connection.
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 click 'Show Options' to adjust additional settings, then connect.
Troubleshoot a connection
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If you are having trouble connecting to a virtual machine over your VPN connection, check the following:
Verify that your VPN connection is successful.
Verify that you are connecting to the private IP address for the VM.
If you can connect to the VM using the private IP address, but not the computer name, verify that you have configured DNS properly. For more information about how name resolution works for VMs, see Name Resolution for VMs.
For more information about RDP connections, see Troubleshoot Remote Desktop connections to a VM.
Verify that the VPN client configuration package was generated after the DNS server IP addresses were specified for the VNet. If you updated the DNS server IP addresses, generate and install a new VPN client configuration package.
Use 'ipconfig' to check the IPv4 address assigned to the Ethernet adapter on the computer from which you are connecting. If the IP address is within the address range of the VNet that you are connecting to, or within the address range of your VPNClientAddressPool, this is referred to as an overlapping address space. When your address space overlaps in this way, the network traffic doesn't reach Azure, it stays on the local network.
To add or remove a root certificate
You can add and remove trusted root certificates from Azure. When you remove a root certificate, clients that have a certificate generated from the root certificate can't authenticate and won't 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 (uploaded) to Azure. These steps require Azure PowerShell cmdlets installed locally on your computer (not Azure Cloud Shell). You can also use the Azure portal to add root certificates.
To add:
You can add up to 20 root certificate .cer files to Azure. The following steps help you add a root certificate.
Prepare the .cer file to upload:
Upload the file. You can only upload one file at a time.
To verify that the certificate file uploaded:
To remove:
Declare the variables. Modify the variables in the example to match the certificate that you want to remove.
Remove the certificate.
Use the following example to verify that the certificate was removed successfully.
To revoke or reinstate a client certificate
You can revoke client certificates. The certificate revocation list allows you to selectively deny point-to-site connectivity based on individual client certificates. This is different than removing a trusted root certificate. If you remove a trusted root certificate .cer from Azure, it revokes the access for all client certificates generated/signed by the revoked root certificate. Revoking a client certificate, rather than the root certificate, allows the other certificates that were generated from the root certificate to continue to be used for authentication.
The common practice is to use the root certificate to manage access at team or organization levels, while using revoked client certificates for fine-grained access control on individual users.
To revoke:
Retrieve the client certificate thumbprint. For more information, see How to retrieve the Thumbprint of a Certificate.
Copy the information to a text editor and remove all spaces so that it is a continuous string. This string is declared as a variable in the next step.
Declare the variables. Make sure to declare the thumbprint you retrieved in the previous step.
Add the thumbprint to the list of revoked certificates. You see 'Succeeded' when the thumbprint has been added.
Verify that the thumbprint was added to the certificate revocation list.
After the thumbprint has been added, the certificate can no longer be used to connect. Clients that try to connect using this certificate receive a message saying that the certificate is no longer valid.
To reinstate:
You can reinstate a client certificate by removing the thumbprint from the list of revoked client certificates.
Declare the variables. Make sure you declare the correct thumbprint for the certificate that you want to reinstate.
Remove the certificate thumbprint from the certificate revocation list.
Check if the thumbprint is removed from the revoked list.
Point-to-Site FAQ
For additional point-to-site information, see the VPN Gateway point-to-site FAQ
Next steps
Once your connection is complete, you can add virtual machines to your virtual networks. For more information, see Virtual Machines. To understand more about networking and virtual machines, see Azure and Linux VM network overview.
For P2S troubleshooting information, Troubleshooting: Azure point-to-site connection problems.