Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Always On VPN Clients Prompted for Authentication when Accessing Internal ResourcesWhen deploying Windows 10 Always On VPN using Protected Extensible Authentication Protocol (PEAP) with client authentication certificates, the administrator may encounter a scenario in which the user can establish a VPN connection without issue, but when accessing internal resources they are prompted for credentials and receive the following error message.

“The system cannot contact a domain controller to service the authentication request. Please try again later.”

Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Resolution

This can occur if one or more domain controllers in the enterprise have expired or missing domain controller authentication certificates. To ensure seamless single sign-on to internal resources, ensure that all domain controllers have a certificate issued by the internal certification authority (CA) that includes the Server Authentication (1.3.6.1.5.5.7.3.1), Client Authentication (1.3.6.1.5.5.7.3.2), KDC Authentication (1.3.6.1.5.2.3.5), and Smart Card Logon (1.3.6.1.4.1.311.20.2.2) Enhanced Key Usage (EKU). Administrators can duplicate the Kerberos Authentication template for this purpose.

Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Additional Information

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Hands-On Training

 

What is the Difference Between DirectAccess and Always On VPN?

Always On VPN Device Tunnel Configuration Guidance Now AvailableDirectAccess has been around for many years, and with Microsoft now moving in the direction of Always On VPN, I’m often asked “What’s the difference between DirectAccess and Always On VPN?” Fundamentally they both provide seamless and transparent, always on remote access. However, Always On VPN has a number of advantages over DirectAccess in terms of security, authentication and management, performance, and supportability.

Security

DirectAccess provides full network connectivity when a client is connected remotely. It lacks any native features to control access on a granular basis. It is possible to restrict access to internal resources by placing a firewall between the DirectAccess server and the LAN, but the policy would apply to all connected clients.

Windows 10 Always On VPN includes support for granular traffic filtering. Where DirectAccess provides access to all internal resources when connected, Always On VPN allows administrators to restrict client access to internal resources in a variety of ways. In addition, traffic filter policies can be applied on a per-user or group basis. For example, users in accounting can be granted access only to their department servers. The same could be done for HR, finance, IT, and others.

Authentication and Management

DirectAccess includes support for strong user authentication with smart cards and one-time password (OTP) solutions. However, there is no provision to grant access based on device configuration or health, as that feature was removed in Windows Server 2016 and Windows 10. In addition, DirectAccess requires that clients and servers be joined to a domain, as all configuration settings are managed using Active Directory group policy.

Windows 10 Always On VPN includes support for modern authentication and management, which results in better overall security. Always On VPN clients can be joined to an Azure Active Directory and conditional access can also be enabled. Modern authentication support using Azure MFA and Windows Hello for Business is also supported. Always On VPN is managed using Mobile Device Management (MDM) solutions such as Microsoft Intune.

Performance

DirectAccess uses IPsec with IPv6, which must be encapsulated in TLS to be routed over the public IPv4 Internet. IPv6 traffic is then translated to IPv4 on the DirectAccess server. DirectAccess performance is often acceptable when clients have reliable, high quality Internet connections. However, if connection quality is fair to poor, the high protocol overhead of DirectAccess with its multiple layers of encapsulation and translation often yields poor performance.

The protocol of choice for Windows 10 Always On VPN deployments is IKEv2. It offers the best security and performance when compared to TLS-based protocols. In addition, Always On VPN does not rely exclusively on IPv6 as DirectAccess does. This reduces the many layers of encapsulation and eliminates the need for complex IPv6 transition and translation technologies, further improving performance over DirectAccess.

Supportability

DirectAccess is a Microsoft-proprietary solution that must be deployed using Windows Server and Active Directory. It also requires a Network Location Server (NLS) for clients to determine if they are inside or outside the network. NLS availability is crucial and ensuring that it is always reachable by internal clients can pose challenges, especially in very large organizations.

Windows 10 Always On VPN supporting infrastructure is much less complex than DirectAccess. There’s no requirement for a NLS, which means fewer servers to provision, manage, and monitor. In addition, Always On VPN is completely infrastructure independent and can be deployed using third-party VPN servers such as Cisco, Checkpoint, SonicWALL, Palo Alto, and more.

Summary

Windows 10 Always On VPN is the way of the future. It provides better overall security than DirectAccess, it performs better, and it is easier to manage and support.

Here’s a quick summary of some important aspects of VPN, DirectAccess, and Windows 10 Always On VPN.

Traditional VPN DirectAccess Always On VPN
Seamless and Transparent No Yes Yes
Automatic Connection Options None Always on Always on, app triggered
Protocol Support IPv4 and IPv6 IPv6 Only IPv4 and IPv6
Traffic Filtering No No Yes
Azure AD Integration No No Yes
Modern Management Yes No (group policy only) Yes (MDM)
Clients must be domain-joined? No Yes No
Requires Microsoft Infrastructure No Yes No
Supports Windows 7 Yes Yes Windows 10 only

Always On VPN Hands-On Training

If you are interested in learning more about Windows 10 Always On VPN, consider registering for one of my hands-on training classes. More details here.

Additional Resources

Always On VPN and the Future of Microsoft DirectAccess

5 Important Things DirectAccess Administrators Should Know about Windows 10 Always On VPN

3 Important Advantages of Windows 10 Always On VPN over DirectAccess

Managing and Supporting DirectAccess with Windows Server 2016 Video Training Course on Pluralsight

Planning and Implementing DirectAccess with Windows Server 2016I’m pleased to announce my newest video training course, Managing and Supporting DirectAccess with Windows Server 2016, is now available on Pluralsight! This new course is a follow-up to my previous course, Planning and Implementing DirectAccess with Windows Server 2016. This latest course builds upon the first one and covers advanced configuration such as enabling load balancing, configuring geographic redundancy, and enforcing strong user authentication using one-time passwords (OTP) and smart cards.

In addition, monitoring and reporting is covered, as well as implementing manage out for DirectAccess clients in supported scenarios. The course also includes a full hour of in-depth DirectAccess configuration and connectivity troubleshooting that will be valuable for all DirectAccess administrators.

The course includes the following training modules:

Configuring High Availability
Enabling Strong User Authentication
DirectAccess Monitoring and Reporting
Implementing Outbound Management for DirectAccess Clients
DirectAccess Troubleshooting

Throughout the course, I share valuable knowledge and insight gained from more than 5 years of experience deploying DirectAccess for some of the largest organizations in the world. Pluralsight offers a free trial subscription if you don’t already have one, so watch my latest DirectAccess video training course today!

Additional Resources

Planning and Implementing DirectAccess with Windows Server 2016 on Pluralsight
Managing and Supporting DirectAccess with Windows Server 2016 on Pluralsight
Implementing DirectAccess with Windows Server 2016 book