VPN and conditional access

The VPN client is now able to integrate with the cloud-based Conditional Access Platform to provide a device compliance option for remote clients. Conditional Access is a policy-based evaluation engine that lets you create access rules for any Microsoft Entra connected application.


Conditional Access is a Microsoft Entra ID P1 or P2 feature.

Conditional Access Platform components used for Device Compliance include the following cloud-based services:

  • Conditional Access Framework
  • Microsoft Entra Connect Health
  • Windows Health Attestation Service (optional)
  • Microsoft Entra Certificate Authority - It's a requirement that the client certificate used for the cloud-based device compliance solution be issued by a Microsoft Entra ID-based Certificate Authority (CA). A Microsoft Entra CA is essentially a mini-CA cloud tenant in Azure. The Microsoft Entra CA can't be configured as part of an on-premises Enterprise CA. See also Always On VPN deployment for Windows Server and Windows 10.
  • Microsoft Entra ID-issued short-lived certificates - When a VPN connection attempt is made, the Microsoft Entra Token Broker on the local device communicates with Microsoft Entra ID, which then checks for health based on compliance rules. If compliant, Microsoft Entra ID sends back a short-lived certificate that is used to authenticate the VPN. Note that certificate authentication methods such as EAP-TLS can be used. When the client reconnects and determines that the certificate has expired, the client will again check with Microsoft Entra ID for health validation before a new certificate is issued.
  • Microsoft Intune device compliance policies: Cloud-based device compliance uses Microsoft Intune Compliance Policies, which are capable of querying the device state and define compliance rules for the following, among other things.
    • Antivirus status
    • Auto-update status and update compliance
    • Password policy compliance
    • Encryption compliance
    • Device health attestation state (validated against attestation service after query)

The following client-side components are also required:

VPN device compliance

At this time, the Microsoft Entra certificates issued to users don't contain a CRL Distribution Point (CDP) and aren't suitable for Key Distribution Centers (KDCs) to issue Kerberos tokens. For users to gain access to on-premises resources such as files on a network share, client authentication certificates must be deployed to the Windows profiles of the users, and their VPNv2 profiles must contain the <SSO> section.

Server-side infrastructure requirements to support VPN device compliance include:

  • The VPN server should be configured for certificate authentication.
  • The VPN server should trust the tenant-specific Microsoft Entra CA.
  • For client access using Kerberos/NTLM, a domain-trusted certificate is deployed to the client device and is configured to be used for single sign-on (SSO).

After the server side is set up, VPN admins can add the policy settings for conditional access to the VPN profile using the VPNv2 DeviceCompliance node.

Two client-side configuration service providers are leveraged for VPN device compliance.

  • VPNv2 CSP DeviceCompliance settings:
    • Enabled: enables the Device Compliance flow from the client. If marked as true, the VPN client attempts to communicate with Microsoft Entra ID to get a certificate to use for authentication. The VPN should be set up to use certificate authentication and the VPN server must trust the server returned by Microsoft Entra ID.
    • Sso: entries under SSO should be used to direct the VPN client to use a certificate other than the VPN authentication certificate when accessing resources that require Kerberos authentication.
    • Sso/Enabled: if this field is set to true, the VPN client looks for a separate certificate for Kerberos authentication.
    • Sso/IssuerHash: hashes for the VPN client to look for the correct certificate for Kerberos authentication.
    • Sso/Eku: comma-separated list of extended key usage (EKU) extensions for the VPN client to look for the correct certificate for Kerberos authentication.
  • HealthAttestation CSP (not a requirement) - functions performed by the HealthAttestation CSP include:
    • Collects TPM data used to verify health states
    • Forwards the data to the Health Attestation Service (HAS)
    • Provisions the Health Attestation Certificate received from the HAS
    • Upon request, forward the Health Attestation Certificate (received from HAS) and related runtime information to the MDM server for verification


It's required that certificates used for obtaining Kerberos tickets to be issued from an on-premises CA, and that SSO to be enabled in the user's VPN profile. This will enable the user to access on-premises resources. In the case of AzureAD-only joined devices (not hybrid joined devices), if the user certificate issued by the on-premises CA has the user UPN from AzureAD in Subject and SAN (Subject Alternative Name), the VPN profile must be modified to ensure that the client does not cache the credentials used for VPN authentication. To do this, after deploying the VPN profile to the client, modify the Rasphone.pbk on the client by changing the entry UseRasCredentials from 1 (default) to 0 (zero).

Client connection flow

The VPN client side connection flow works as follows:

Device compliance workflow when VPN client attempts to connect.

When a VPNv2 Profile is configured with <DeviceCompliance> <Enabled>true</Enabled> the VPN client uses this connection flow:

  1. The VPN client calls into Windows 10's or Windows 11's Microsoft Entra Token Broker, identifying itself as a VPN client.
  2. The Microsoft Entra Token Broker authenticates to Microsoft Entra ID and provides it with information about the device trying to connect. The Microsoft Entra Server checks if the device is in compliance with the policies.
  3. If compliant, Microsoft Entra ID requests a short-lived certificate.
  4. Microsoft Entra ID pushes down a short-lived certificate to the Certificate Store via the Token Broker. The Token Broker then returns control back over to the VPN client for further connection processing.
  5. The VPN client uses the Microsoft Entra ID-issued certificate to authenticate with the VPN server.

Configure conditional access

See VPN profile options and VPNv2 CSP for XML configuration.

Learn more about Conditional Access and Microsoft Entra Health