Always On VPN at MMSMOA 2022

I am excited to announce that I will be presenting at this year’s Midwest Management Summit at the Mall of America (MMSMOA) in Bloomington, Minnesota. The conference takes place the week of May 2. This is my first time presenting at this event, and I’m looking forward to sharing my experience deploying enterprise mobility and security infrastructure solutions with systems management professionals from around the world.

Sessions

I will be delivering three talks at the conference addressing various secure remote access and certificate services topics.

Managing Always On VPN with Intune

This session will provide administrators with everything they need to know about provisioning and managing Always On VPN client configuration settings using Intune. I’ll be providing tips, tricks, and best practices for Always On VPN profile configuration and demonstrating many of the limitations associated with using Intune. I will provide workarounds whenever possible.

Managing Always On VPN with Intune: The Good, The Bad, and the Ugly

Always On VPN Gateway Options in Azure

Deploying Always On VPN in Azure is increasingly common. However, administrators are unaware of the limitations of supporting Always On VPN connections with native Azure VPN gateway solutions. In this session, I’ll describe in detail what’s required to support Always On VPN and, importantly, what the limitations are.

Always On VPN Gateway Options in Azure

Deploying On-premises PKI Certificates with Intune

As organizations continue to migrate applications, services, and infrastructure to the cloud, the requirement for endpoints to be joined to an on-premises domain is fading. Moving to full Intune management and native Azure Active Directory join for endpoints is increasingly common. However, deploying enterprise PKI certificates o these endpoints is often required. This session will provide detailed guidance for choosing the best solution to deliver on-premises certificates to Azure AD joined devices using Intune.

Deploying on-premises PKI Certificates with Intune

Let’s Connect

I’m looking forward to meeting so many folks who have helped me get up to speed with Microsoft Endpoint Manager/Intune over the years. If you’re attending the conference, or if you are in the area, be sure to reach out. Let’s grab a beer and chat!

Additional Information

Midwest Management Summit at Mall of America (MMSMOA) 2022

Managing Always On VPN with Intune: The Good, The Bad, and the Ugly

Always On VPN Gateway Options in Azure

Deploying on-premises PKI Certificates with Intune

Always On VPN Error -2146762495

DirectAccess Troubleshooting and the Windows 10 Network Connectivity Assistant

Always On VPN Administrators may encounter a scenario where Always On VPN connections suddenly stop working for all clients using the Secure Socket Tunneling Protocol (SSTP) VPN protocol. IKEv2 VPN connections continue to work, however.

Event Log

Reviewing the event log on a client machine reveals an error event ID 20227 from the RasClient source. The error message states the following.

“The user [username] dialed a connection named [connection name] which has failed. The error code returned on failure is -2146762495.”

Error -2146762495?

Always On VPN administrators will be familiar with error codes such as 809, 691 and 812, 853, 858, and even 13801, 13806, and 13868. However, this error code seems to be formatted much differently. As it turns out, this message is in decimal format. Thankfully it’s pretty easy to convert it to something more meaningful, like hexadecimal. To do this, open the Windows calculator (calc.exe) and switch to programmer mode. Highlight DEC and enter -2146762495. The hexadecimal value will be displayed in the HEX field, as shown here.

Error 0x800B0101

After converting the error message from decimal to hex, use the Microsoft Error Lookup tool (err.exe) to translate the hex value of this error. As shown here, 0x800B0101 translates to CERT_E_EXPIRED.

Expired TLS Certificate

Once again, an expired certificate is to blame! In this case, the TLS certificate installed on the VPN server has expired and is no longer valid.

Resolution

The problem is simple enough to resolve, of course. Obtain a new TLS certificate from your certification authority (CA) of choice and update your VPN server configuration. You can find detailed guidance for updating the RRAS VPN server’s TLS certificate here. You will also find a video demonstration of the RRAS SSL/TLS certificate renewal process here.

Additional Information

Installing or Renewing an SSL/TLS Certificate on Windows Server RRAS for Always On VPN and SSTP

VIDEO: Installing or Renewing an SSL/TLS certificate on Windows Server RRAS for Always On VPN and SSTP

Microsoft Windows Always On VPN SSTP Security Configuration

Microsoft Windows Always On VPN SSL/TLS Certificate Requirements for SSTP

Microsoft Windows Always On VPN SSTP with Let’s Encrypt Certificates

Always On VPN SSTP Certificate Renewal

Windows Server Routing and Remote Access Service (RRAS) is popular for Always On VPN deployments because it supports the Secure Socket Tunneling Protocol (SSTP). The SSTP VPN protocol is recommended for use with the Always On VPN user tunnel because it is firewall friendly. Installing a TLS certificate on the VPN server is necessary to support SSTP VPN connections. Administrators should use a TLS certificate signed by a public certification authority (CA) for optimal reliability and performance.

Click here to view a video demonstration of the procedures outlined in this article.

Certificate Expiration

Of course, all certificates expire, and the TLS certificate used for SSTP is no exception. When using a public TLS certificate, the certificate lifetime is typically no more than one year, which means Always On VPN administrators will be renewing this certificate regularly.

Certificate Renewal

The process of “renewing” an SSTP TLS certificate is essentially the same as installing a new one, as it is best to create a new public/private key pair when renewing a certificate. The following outlines the steps required to generate a Certificate Signing Request (CSR), import the certificate, then assign the certificate to the SSTP listener on the VPN server.

Note: The guidance provided here assumes using an ECC certificate, which is best for optimal security and performance. More details here.

Certificate Request

Open the local computer certificate store (certlm.msc) on the VPN server and perform the following steps to generate a new CSR.

  1. Expand Certificates – Local Computer > Personal.
  2. Right-click the Certificates folder and choose All Tasks > Advanced Operations > Create Custom Request.
  3. Click Next.
  4. Highlight Proceed without enrollment policy.
  5. Click Next.
    1. Select (No template) CNG key from the Template drop-down list.
    2. Select PKCS #10 in the Request format section.
    3. Click Next.
  6. Click on the down arrow next to Details.
    Always On VPN ECDSA SSL Certificate Request for SSTP
  7. Click on the Properties button.
  8. Select the General tab.
    1. Enter the public hostname for the certificate in the Friendly name field.
  9. Select the Subject tab.
    1. Select Common name from the Type drop-down list in the Subject name section.
    2. Enter the public hostname for the certificate in the Value field.
    3. Click Add.
    4. In the Alternative name section, select DNS from the Type drop-down list.
    5. Enter the public hostname for the certificate in the Value field.
    6. Click Add.
      Always On VPN ECDSA SSL Certificate Request for SSTP
  10. Select the Extensions tab.
    1. Expand the Extended Key Usage section.
    2. Select Server Authentication from the Available options section.
    3. Click Add.
      Always On VPN ECDSA SSL Certificate Request for SSTP
  11. Select the Private Key tab.
    1. Expand the Cryptographic Service Provider section.
      1. Uncheck the box next to RSA,Microsoft Software Key Storage Provider.
      2. Check the box next to ECDSA_P256,Microsoft Software Key Storage Provider.
    2. Expand the Key options section.
      1. Check the box next to Make private key exportable.
        Always On VPN ECDSA SSL Certificate Request for SSTP
  12. Click Ok.
  13. Click Next.
  14. Enter a name for the file in the File Name field.
  15. Select Base 64 in the File format section.
  16. Click Finish.

Import Certificate

Once complete, submit the file created to a public CA for signing. When the CA returns the signed certificate, perform the following steps to import it to the local compute certificate store.

  1. Right-click the Certificates folder and choose All Tasks > Import.
  2. Click Next.
  3. Enter the name of the certificate file returned by the public CA in the File name field.
  4. Click Next.
  5. Select Place all certificates in the following store and ensure that Personal is listed in the Certificate store field.
  6. Click Next.
  7. Click Finish.
  8. Click Ok.

Assign Certificate

After importing the new TLS certificate in the local computer’s certificate store, open the Routing and Remote Access management console (rrasmgmt.msc) and perform the following steps to assign the TLS certificate to the SSTP listener.

  1. Right-click the VPN server and choose Properties.
  2. Select the Security tab.
    1. Select the new TLS certificate from the Certificate drop-down list in the SSL Certificate Binding section. When replacing an existing certificate, you may see a certificate with the same name more than once. Click the View button and ensure the new certificate is selected.
    2. Click Ok.
    3. Click Yes to restart the RemoteAccess service.

Demonstration Video

A recorded video demonstration of this process can be found here. The video recording also includes guidance for making these changes on Windows Server Core servers.

Additional Information

Installing or Renewing an SSL/TLS Certificate on Windows Server for Always On VPN and SSTP.

Microsoft Windows Always On VPN SSTP Security Configuration

Microsoft Windows Always On VPN SSL Certificate Requirements for SSTP

Microsoft Windows Always On VPN ECDSA TLS Certificate Request for SSTP

Microsoft Windows Always On VPN SSTP with Let’s Encrypt Certificates

%d bloggers like this: