Generate and export certificates for Point-to-Site connections using PowerShell on Windows 10

Point-to-Site connections use certificates to authenticate. This article shows you how to create a self-signed root certificate and generate client certificates using PowerShell on Windows 10. If you are looking for Point-to-Site configuration steps, such as how to upload root certificates, select one of the 'Configure Point-to-Site' articles from the following list:

You must perform the steps in this article on a computer running Windows 10. The PowerShell cmdlets that you use to generate certificates are part of the Windows 10 operating system and do not work on other versions of Windows. The Windows 10 computer is only needed to generate the certificates. Once the certificates are generated, you can upload them, or install them on any supported client operating system.

If you do not have access to a Windows 10 computer, you can use MakeCert to generate certificates. The certificates that you generate using either method can be installed on any supported client operating system.

Create a self-signed root certificate

Use the New-SelfSignedCertificate cmdlet to create a self-signed root certificate. For additional parameter information, see New-SelfSignedCertificate.

  1. From a computer running Windows 10, open a Windows PowerShell console with elevated privileges.
  2. Use the following example to create the self-signed root certificate. The following example creates a self-signed root certificate named 'P2SRootCert' that is automatically installed in 'Certificates-Current User\Personal\Certificates'. You can view the certificate by opening certmgr.msc, or Manage User Certificates.

    $cert = New-SelfSignedCertificate -Type Custom -KeySpec Signature `
    -Subject "CN=P2SRootCert" -KeyExportPolicy Exportable `
    -HashAlgorithm sha256 -KeyLength 2048 `
    -CertStoreLocation "Cert:\CurrentUser\My" -KeyUsageProperty Sign -KeyUsage CertSign
    

Export the public key (.cer)

Point-to-Site connections require the certificate public key .cer file (not the private key) to be uploaded to Azure. The following steps help you export the .cer file for your self-signed root certificate:

  1. To obtain a .cer file from the certificate, open Manage user certificates. Locate the self-signed root certificate, typically in 'Certificates - Current User\Personal\Certificates', and right-click. Click All Tasks, and then click Export. This opens the Certificate Export Wizard.
  2. In the Wizard, click Next. Select No, do not export the private key, and then click Next.
  3. On the Export File Format page, select Base-64 encoded X.509 (.CER)., and then click Next.
  4. On the File to Export, Browse to the location to which you want to export the certificate. For File name, name the certificate file. Then, click Next.
  5. Click Finish to export the certificate. You see The export was successful. Click OK to close the wizard.

The exported.cer file must be uploaded to Azure. For instructions, see Configure a Point-to-Site connection. To add an additional trusted root certificate, this section of the article.

Export the self-signed root certificate and public key to store it (optional)

You may want to export the self-signed root certificate and store it safely. If need be, you can later install it on another computer and generate more client certificates, or export another .cer file. To export the self-signed root certificate as a .pfx, select the root certificate and use the same steps as described in Export a client certificate.

Generate a client certificate

Each client computer that connects to a VNet using Point-to-Site must have a client certificate installed. You generate a client certificate from the self-signed root certificate, and then export and install the client certificate. If the client certificate is not installed, authentication fails.

The following steps walk you through generating a client certificate from a self-signed root certificate. You may generate multiple client certificates from the same root certificate. When you generate client certificates using the steps below, the client certificate is automatically installed on the computer that you used to generate the certificate. If you want to install a client certificate on another client computer, you can export the certificate.

The examples use the New-SelfSignedCertificate cmdlet to generate a client certificate that expires in one year. For additional parameter information, such as setting a different expiration value for the client certificate, see New-SelfSignedCertificate.

Example 1

This example uses the declared '$cert' variable from the previous section. If you closed the PowerShell console after creating the self-signed root certificate, or are creating additional client certificates in a new PowerShell console session, use the steps in Example 2.

Modify and run the example to generate a client certificate. If you run the following example without modifying it, the result is a client certificate named 'P2SChildCert'. If you want to name the child certificate something else, modify the CN value. Do not change the TextExtension when running this example. The client certificate that you generate is automatically installed in 'Certificates - Current User\Personal\Certificates' on your computer.

New-SelfSignedCertificate -Type Custom -KeySpec Signature `
-Subject "CN=P2SChildCert" -KeyExportPolicy Exportable `
-HashAlgorithm sha256 -KeyLength 2048 `
-CertStoreLocation "Cert:\CurrentUser\My" `
-Signer $cert -TextExtension @("2.5.29.37={text}1.3.6.1.5.5.7.3.2")

Example 2

If you are creating additional client certificates, or are not using the same PowerShell session that you used to create your self-signed root certificate, use the following steps:

  1. Identify the self-signed root certificate that is installed on the computer. This cmdlet returns a list of certificates that are installed on your computer.

    Get-ChildItem -Path “Cert:\CurrentUser\My”
    
  2. Locate the subject name from the returned list, then copy the thumbprint that is located next to it to a text file. In the following example, there are two certificates. The CN name is the name of the self-signed root certificate from which you want to generate a child certificate. In this case, 'P2SRootCert'.

    Thumbprint                                Subject
    
    AED812AD883826FF76B4D1D5A77B3C08EFA79F3F  CN=P2SChildCert4
    7181AA8C1B4D34EEDB2F3D3BEC5839F3FE52D655  CN=P2SRootCert
    
  3. Declare a variable for the root certificate using the thumbprint from the previous step. Replace THUMBPRINT with the thumbprint of the root certificate from which you want to generate a child certificate.

    $cert = Get-ChildItem -Path "Cert:\CurrentUser\My\THUMBPRINT"
    

    For example, using the thumbprint for P2SRootCert in the previous step, the variable looks like this:

    $cert = Get-ChildItem -Path "Cert:\CurrentUser\My\7181AA8C1B4D34EEDB2F3D3BEC5839F3FE52D655"
    
  4. Modify and run the example to generate a client certificate. If you run the following example without modifying it, the result is a client certificate named 'P2SChildCert'. If you want to name the child certificate something else, modify the CN value. Do not change the TextExtension when running this example. The client certificate that you generate is automatically installed in 'Certificates - Current User\Personal\Certificates' on your computer.

    New-SelfSignedCertificate -Type Custom -KeySpec Signature `
    -Subject "CN=P2SChildCert" -KeyExportPolicy Exportable `
    -HashAlgorithm sha256 -KeyLength 2048 `
    -CertStoreLocation "Cert:\CurrentUser\My" `
    -Signer $cert -TextExtension @("2.5.29.37={text}1.3.6.1.5.5.7.3.2")
    

Export a client certificate

When you generate a client certificate, it's automatically installed on the computer that you used to generate it. If you want to install the client certificate on another client computer, you need to export the client certificate that you generated.

  1. To export a client certificate, open Manage user certificates. The client certificates that you generated are, by default, located in 'Certificates - Current User\Personal\Certificates'. Right-click the client certificate that you want to export, click all tasks, and then click Export to open the Certificate Export Wizard.
  2. In the Wizard, click Next, then select Yes, export the private key, and then click Next.
  3. On the Export File Format page, leave the defaults selected. Make sure that Include all certificates in the certification path if possible is selected. Selecting this also exports the root certificate information that is required for successful authentication. Then, click Next.
  4. On the Security page, you must protect the private key. If you select to use a password, make sure to record or remember the password that you set for this certificate. Then, click Next.
  5. On the File to Export, Browse to the location to which you want to export the certificate. For File name, name the certificate file. Then, click Next.
  6. Click Finish to export the certificate.

Install an exported 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.

  1. 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 click Next.
  2. On the File to import page, don't make any changes. Click Next.
  3. On the Private key protection page, input the password for the certificate, or verify that the security principal is correct, then click Next.
  4. On the Certificate Store page, leave the default location, and then click Next.
  5. Click Finish. On the Security Warning for the certificate installation, click Yes. You can feel comfortable clicking 'Yes' because you generated the certificate. The certificate is now successfully imported.

Next steps

Continue with your Point-to-Site configuration.