Always On VPN Certificate Requirements for IKEv2

Always On VPN Certificate Requirements for IKEv2Internet Key Exchange version 2 (IKEv2) is one of the VPN protocols supported for Windows 10 Always On VPN deployments. When the VPN server is Windows Server 2016 with the Routing and Remote Access Service (RRAS) role configured, a computer certificate must first be installed on the server to support IKEv2. There are some unique requirements for this certificate, specifically regarding the subject name and Enhanced Key Usage (EKU) configuration. In addition, some deployment scenarios may require a certificate to be provisioned to the client to support IKEv2 VPN connections.

Server Certificate

The IKEv2 certificate on the VPN server must be issued by the organization’s internal private certification authority (CA). It must be installed in the Local Computer/Personal certificate store on the VPN server. The subject name on the certificate must match the public hostname used by VPN clients to connect to the server, not the server’s hostname. For example, if the VPN server’s hostname is VPN1 and the public FQDN is vpn.example.net, the subject field of the certificate must include vpn.example.net, as shown here.

Always On VPN Certificate Requirements for IKEv2

In addition, the certificate must include the Server Authentication EKU (1.3.6.1.5.5.7.3.1). Optionally, but recommended, the certificate should also include the IP security IKE intermediate EKU (1.3.6.1.5.5.8.2.2).

Always On VPN Certificate Requirements for IKEv2

Client Certificate

Client certificate requirements vary depending on the type of VPN tunnel and authentication method being used.

User Tunnel

No certificates are required on the client to support IKEv2 when using MSCHAPv2, EAP-MSCHAPv2, or Protected EAP (PEAP) with MSCHAPv2. However, if the option to verify the server’s identity by validating the certificate is selected when using PEAP, the client must have the certificates for the root CA and any subordinate CAs installed in its Trusted Root Certification and Intermediate Certificate Authorities certificate stores, respectively.

User Tunnel with Certificate Authentication

Using certificate authentication for the user tunnel is the recommended best practice for Always On VPN deployments. A client certificate must be installed in the Current User/Personal store to support PEAP authentication with smart card or certificate authentication. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

Device Tunnel

A computer certificate must be installed in the Local Computer/Personal certificate store to support IKEv2 machine certificate authentication and the Always On VPN device tunnel. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

More information about configuring the Always On VPN device tunnel can be found here.

Additional Information

Always On VPN with Trusted Platform Module (TPM) Certificates

Always On VPN Protocol Recommendations for Windows Server 2016 RRAS

Always On VPN and Windows Server RRAS

Always On VPN Training

Configuring Multiple Windows Server 2012 R2 DirectAccess Instances

DirectAccess in Windows Server 2012 R2 supports many different deployment configurations. It can be deployed with a single server, multiple servers in a single location, multiple servers in multiple locations, edge facing, in a perimeter or DMZ network, etc.

Global Settings

There are a number of important DirectAccess settings that are global in scope and apply to all DirectAccess clients, such as certificate authentication, force tunneling, one-time password, and many more. For example, if you configure DirectAccess to use Kerberos Proxy instead of certificates for authentication, Windows 7 clients are not supported. In this scenario it is advantageous to have a second parallel DirectAccess deployment configured specifically for Windows 7 clients. This allows Windows 8 clients to take advantage of the performance gains afforded by Kerberos Proxy, while at the same time providing an avenue of support for Windows 7 clients.

Parallel Deployments

To the surprise of many, it is indeed possible to deploy DirectAccess more than once in an organization. I’ve been helping customers deploy DirectAccess for nearly five years now, and I’ve done this on more than a few occasions. In fact, there are some additional important uses cases that having more than one DirectAccess deployment can address.

Common Use Cases

QA and Testing – Having a separate DirectAccess deployment to perform testing and quality assurance can be quite helpful. Here you can validate configuration changes and verify updates without potential negative impact on the production deployment.

Delegated Administration – DirectAccess provides support for geographic redundancy, allowing administrators to create DirectAccess entry points in many different locations. DirectAccess in Windows Server 2012 R2 lacks support for delegated administration though, and in some cases it may make more sense to have multiple separate deployments as opposed to a single, multisite deployment. For example, many organizations are divided in to different business units internally and may operate autonomously. They may also have different configuration requirements, which can be better addressed using individual DirectAccess implementations.

Migration – If you have currently deployed DirectAccess using Windows Server 2008 R2 with or without Forefront UAG 2010, migrating to Windows Server 2012 R2 can be challenging because a direct, in-place upgrade is not supported. You can, however, deploy DirectAccess using Windows Server 2012 R2 in parallel to your existing deployment and simply migrate users to the new solution by moving the DirectAccess client computer accounts to a new security group assigned to the new deployment.

Major Configuration Changes – This strategy is also useful for scenarios where implementing changes to the DirectAccess configuration would be disruptive for remote users. For example, changing from a single site to a multisite configuration would typically require that all DirectAccess clients be on the LAN or connect remotely out-of-band to receive group policy settings changes after multisite is first configured. In addition, parallel deployments can significantly ease the pain of transitioning to a new root CA if required.

Unique Client Requirements – Having a separate deployment may be required to take advantage of the unique capabilities of each client operating system. For example, Windows 10 clients do not support Microsoft Network Access Protection (NAP) integration. NAP is a global setting in DirectAccess and applies to all clients. If you still require NAP integration and endpoint validation using NAP for Windows 7 and Windows 8.x, another DirectAccess deployment will be required to support Windows 10 clients.

Requirements

To support multiple Windows Server 2012 R2 DirectAccess deployments in the same organization, the following is required:

Unique IP Addresses – It probably goes without saying, but each DirectAccess deployment must have unique internal and external IPv4 addresses.

Distinct Public Hostname – The public hostname used for each deployment must also be unique. Multi-SAN certificates have limited support for DirectAccess IP-HTTPS (public hostname must be the first entry in the list), so consider using a wildcard certificate or obtain certificates individually for each deployment.

Group Policy Objects – You must use unique Active Directory Group Policy Objects (GPOs) to support multiple DirectAccess deployments in a single organization. You have the option to specify a unique GPO when you configure DirectAccess for the first time by clicking the Change link next to GPO Settings on the Remote Access Review screen.

Configuring Multiple Windows Server 2012 R2 DirectAccess Instances

Enter a distinct name for both the client and server GPOs. Click Ok and then click Apply to apply the DirectAccess settings for this deployment.

Configuring Multiple Windows Server 2012 R2 DirectAccess Instances

Windows 7 DirectAccess Connectivity Assistant (DCA) GPOs – If the DirectAccess Connectivity Assistant (DCA) v2.0 has been deployed for Windows 7 clients, separate GPOs containing the DCA client settings for each individual deployment will have to be configured. Each DirectAccess deployment will have unique Dynamic Tunnel Endpoint (DTE) IPv6 addresses which are used by the DCA to confirm corporate network connectivity. The rest of the DCA settings can be the same, if desired.

Supporting Infrastructure

The rest of the supporting infrastructure (AD DS, PKI, NLS, etc.) can be shared between the individual DirectAccess deployments without issue. Once you’ve deployed multiple DirectAccess deployments, make sure that DirectAccess clients DO NOT belong to more than one DirectAccess client security group to prevent connectivity issues.

Migration Process

Moving DirectAccess client computers from the old security group to the new one is all that’s required to migrate clients from one DirectAccess deployment to another. Client machines will need to be restarted to pick up the new security group membership, at which time they will also get the DirectAccess client settings for the new deployment. This works seamlessly when clients are on the internal network. It works well for clients that are outside the network too, for the most part. Because clients must be restarted to get the new settings, it can take some time before all clients finally moved over. To speed up this process it is recommended that DirectAccess client settings GPOs be targeted at a specific OUs created for the migration process. A staging OU is created for clients in the old deployment and a production OU is created for clients to be assigned to the new deployment. DirectAccess client settings GPOs are then targeted at those OUs accordingly. Migrating then only requires moving a DirectAccess client from the old OU to the new one. Since OU assignment does not require a reboot, clients can be migrated much more quickly using this method.

Summary

DirectAccess with Windows Server 2012 R2 supports many different deployment models. For a given DirectAccess deployment model, some settings are global in scope and may not provide the flexibility required by some organizations. To address these challenges, consider a parallel deployment of DirectAccess. This will enable you to take advantage of the unique capabilities of each client operating system, or allow you to meet the often disparate configuration requirements that a single deployment cannot support.

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