All posts tagged Certification Authority

Always On VPN Users Prompted for Certificate

Always On VPN Users Prompted for CertificateWhen deploying Windows 10 Always On VPN using Protected Extensible Authentication Protocol (PEAP) authentication with client certificates, administrators may find the VPN connection does not establish automatically. In this specific scenario the client is prompted to select a certificate to use to authenticate to the VPN server.

Always On VPN Users Prompted for Certificate

Multiple Certificates

This can occur when certificates from multiple Certification Authorities (CAs) are issued to the user that include the Client Authentication Enhanced Key Usage (EKU). When this happens, the user is forced to select the correct certificate to use for VPN authentication.

Clearly this is less than ideal, as it not only breaks the seamless and transparent nature of Always On VPN, the user may select the wrong certificate resulting in authentication failure. Ideally the client should be configured to select the correct certificate without user interaction.

Certificate Selection

Follow the steps below to configure automatic certificate selection for VPN authentication.

  1. On a VPN client, right-click the Always On VPN connection and choose Properties.
  2. Select the Security tab.
  3. In the Authentication section click Properties below Use Extensible Authentication Protocol (EAP).
  4. In the Select Authentication Method section click Configure.
  5. In the When connecting section click Advanced.
  6. Check the box next to Certificate Issuer.
  7. Select the root CA used to issue client authentication certificates for VPN authentication.
  8. Click Ok four times to save the configuration.

Always On VPN Users Prompted for Certificate

Once complete, export the EAP configuration to XML from the VPN client and paste the new settings in Intune or in your custom ProfileXML.

Certificate Purpose

By default, a client certificate requires only the Client Authentication EKU to establish a VPN connection. In some cases, this may not be desirable. For example, consider a deployment where Client Authentication certificates are issued to all users for Wi-Fi authentication. Depending on the Network Policy Server (NPS) configuration, these certificates may also be used to authenticate to the VPN.

VPN Specific Certificate

Follow the steps below to create a user authentication certificate template to be used exclusively for VPN authentication.

Certificate Template

  1. On the CA server, open the Certificate Templates management console (certtmpl.msc).
  2. Right-click the certificate template configured for VPN authentication and choose Properties.
  3. Select the Extension tab.
  4. Highlight Application Policies and click Edit.
  5. Click Add.
  6. Click New.
  7. Enter a descriptive name for the new application policy.
  8. Copy the Object identifier for later use and click Ok four times to save the configuration.

    Always On VPN Users Prompted for Certificate

  9. If certificate autoenrollment is configured and the certificate is already provisioned to users, right-click the certificate template and choose Reenroll All Certificate holders.

Client Configuration

  1. On the VPN client, follow the steps outlined previously to configure certificate selection.
  2. In addition to choosing a certificate issuer, select Extended Key Usage (EKU).
  3. Uncheck All Purpose.
  4. Select Client Authentication and the following EKUs.
  5. Click Add.
  6. Click Add once more.
  7. Enter the name of the custom EKU policy created previously.
  8. Enter the custom EKU object identifier copied previously from the custom policy.

    Always On VPN Users Prompted for Certificate

  9. Click Ok twice.
  10. Uncheck AnyPurpose and the following EKUs.
  11. Click Ok four times to save the configuration.

Always On VPN Users Prompted for Certificate

Once complete, export the EAP configuration to XML from the VPN client and paste the new settings in Intune or in your custom ProfileXML.

Additional Information

Windows 10 Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Get-EapConfiguration PowerShell Script on GitHub

Windows 10 Always On VPN Hands-On Training

7 Comments
by Richard M. Hicks on May 28, 2019  •  Permalink
Posted in Always On VPN, AOVPN, authentication, certificates, enterprise mobility, GitHub, Mobility, ProfileXML, public key infrastructure, Remote Access, Security, VPN, Windows 10, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019, XML
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Posted by Richard M. Hicks on May 28, 2019

https://directaccess.richardhicks.com/2019/05/28/always-on-vpn-users-prompted-for-certificate/

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) and Smart Card Logon (1.3.6.1.4.1.311.20.2.2) Enhanced Key Usage (EKU) at a minimum.

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

3 Comments
by Richard M. Hicks on May 20, 2019  •  Permalink
Posted in Always On VPN, AOVPN, authentication, certificates, Encryption, Enterprise, enterprise mobility, Mobility, Remote Access, routing and remote access service, RRAS, Security, troubleshooting, VPN, Windows 10, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019
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Posted by Richard M. Hicks on May 20, 2019

https://directaccess.richardhicks.com/2019/05/20/always-on-vpn-clients-prompted-for-authentication-when-accessing-internal-resources/

Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Certificate Requirements for SSTPThe Windows Server 2016 Routing and Remote Access Service (RRAS) is commonly deployed as a VPN server for Windows 10 Always On VPN deployments. Using RRAS, Always On VPN administrators can take advantage of Microsoft’s proprietary Secure Socket Tunneling Protocol (SSTP) VPN protocol. SSTP is a Transport Layer Security (TLS) based VPN protocol that uses HTTPS over the standard TCP port 443 to encapsulate and encrypt communication between the Always On VPN client and the RRAS VPN server. SSTP is a firewall-friendly protocol that ensures ubiquitous remote network connectivity. Although IKEv2 is the protocol of choice when the highest level of security is required for VPN connections, SSTP can still provide very good security when implementation best practices are followed.

SSTP Certificate

Since SSTP uses HTTPS for transport, a common SSL certificate must be installed in the Local Computer/Personal/Certificates store on the RRAS VPN server. The certificate must include the Server Authentication Enhanced Key Usage (EKU) at a minimum. Often SSL certificates include both the Server Authentication and Client Authentication EKUs, but the Client Authentication EKU is not strictly required. The subject name on the certificate, or at least one of the Subject Alternative Name entries, must match the public hostname used by VPN clients to connect to the VPN server. Multi-SAN (sometimes referred to as UC certificates) and wildcard certificates are supported.

Always On VPN Certificate Requirements for SSTP

Certification Authority

It is recommended that the SSL certificate used for SSTP be issued by a public Certification Authority (CA). Public CAs typically have their Certificate Revocation Lists (CRLs) hosted on robust, highly available infrastructure. This reduces the chance of failed VPN connection attempts caused by the CRL being offline or unreachable.

Using an SSL certificate issued by an internal, private CA is supported if the CRL for the internal PKI is publicly available.

Key Type

RSA is the most common key type used for SSL certificates. However, Elliptic Curve Cryptography (ECC) keys offer better security and performance, so it is recommended that the SSTP SSL certificate be created using an ECC key instead.

Always On VPN Certificate Requirements for SSTP

To use an ECC key, be sure to specify the use of a Cryptographic Next Generation (CNG) key and select the ECDSA_P256 Microsoft Software Key Storage Provider (CSP) (or greater) when creating the Certificate Signing Request (CSR) for the SSTP SSL certificate.

Always On VPN Certificate Requirements for SSTP

Most public CAs will support certificate signing using ECC and Elliptic Curve Digital Signature Algorithm (ECDSA). If yours does not, find a better CA. 😉

Forward Secrecy

Forward secrecy (sometimes referred to as perfect forward secrecy, or PFS) ensures that session keys can’t be compromised even if the server’s private key is compromised. Using forward secrecy for SSTP is crucial to ensuring the highest levels of security for VPN connections.

To enforce the use of forward secrecy, the TLS configuration on the VPN server should be prioritized to prefer cipher suites with Elliptic Curve Diffie-Hellman Ephemeral (ECDHE) key exchange.

Authenticated Encryption

Authenticated encryption (AE) and authenticated encryption with associated data (AEAD) is a form of encryption that provides better data protection and integrity compared to older block or stream ciphers such as CBC or RC4.

To enforce the use of authenticated encryption, the TLS configuration on the VPN server should be prioritized to prefer cipher suites that support Galois/Counter Mode (GCM) block ciphers.

Important Note: In Windows Server 2016, GCM ciphers can be used with both RSA and ECC certificates. However, in Windows Server 2012 R2 GCM ciphers can only be used when an ECC certificate is used.

SSL Offload

Offloading SSL to a load balancer or application delivery controller (ADC) can be enabled to improve scalability and performance for SSTP VPN connections. I will cover SSL offload for SSTP in detail in a future post.

Summary

SSTP can provide good security for VPN connections when implementation and security best practices are followed. For optimum security, use an SSL certificate with an EC key and optimize the TLS configuration to use forward secrecy and authenticated cipher suites.

Additional Information

Always On VPN ECDSA SSL Certificate Request for SSTP

Always On VPN and Windows Server Routing and Remote Access Service (RRAS)

Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN Certificate Requirements for IKEv2

3 Important Advantages of Always On VPN over DirectAccess

Microsoft SSTP Specification on MSDN

22 Comments
by Richard M. Hicks on July 16, 2018  •  Permalink
Posted in Always On VPN, AOVPN, application delivery controller, certificates, ECC, Elliptic Curve Cryptography, encapsulation, Encryption, Enterprise, enterprise mobility, Load Balancing, Mobility, public key infrastructure, Remote Access, Security, SSL, SSL and TLS, TLS, VPN, Windows 10, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on July 16, 2018

https://directaccess.richardhicks.com/2018/07/16/always-on-vpn-ssl-certificate-requirements-for-sstp/

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

62 Comments
by Richard M. Hicks on April 30, 2018  •  Permalink
Posted in Always On VPN, AOVPN, certificates, enterprise mobility, Mobility, PKI, public key infrastructure, Remote Access, Security, Windows 10, Windows Server 2016
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Posted by Richard M. Hicks on April 30, 2018

https://directaccess.richardhicks.com/2018/04/30/always-on-vpn-certificate-requirements-for-ikev2/

Enabling Secure Remote Administration for the NetMotion Mobility Console

During the initial setup of a NetMotion Mobility gateway server, the administrator must choose to allow either Secure (HTTPS) or Non-secure (HTTP) connections when using the web-based Mobility Console.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Configuring HTTPS

Security best practices dictate HTTPS should be enabled to protect credentials used to log on to the gateway remotely. Immediately after selecting the Secure (https:) option, the administrator is prompted to enter server certificate information. Enter this information and click OK to continue and complete the rest of the configuration as necessary.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Self-Signed Certificate

When logging in to the Mobility console, the administrator is presented with a certificate error indicating there is a problem with the website’s security certificate. This is because the certificate is self-signed by the NetMotion Mobility gateway server and is not trusted.

Enabling Secure Remote Administration for the NetMotion Mobility Console

PKI Issued Certificate

The recommended way to resolve this is to request a certificate from a trusted certification authority (CA). To do this, open the Mobility Management Tool on the Mobility gateway server and click on the Web Server tab.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click on the Server Certificate button and then click New in the Certificate Request section.

Enabling Secure Remote Administration for the NetMotion Mobility Console

In the SAN (subject alternative name) field of the Optional Extension section enter the Fully Qualified Domain Name (FQDN) of the server using the syntax dns:fqdn. Include both the FQDN and the single-label hostname (short name) separated by a comma to ensure both names work without issue. For example:

dns:nm1.lab.richardhicks.net,dns:nm1

Enabling Secure Remote Administration for the NetMotion Mobility Console

Before requesting a certificate from a CA, the root and any intermediate CA certificates must first be imported. Click the Import button next to each, as required.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Copy in the Certificate Request section to copy the Certificate Signing Request (CSR) to the clipboard and then save it to a text file. Now submit the CSR to be signed by the CA using the certreq.exe command. Open an elevated command or PowerShell window and enter the following commands.

certreq.exe -attrib “CertificateTemplate:[TemplateName]” -submit [Path_to_CSR_file]

For example:

certreq.exe -attrib “CertificateTemplate:LabWebServer” -submit certreq.txt

Select a CA from the list and click OK, then save the certificate response when prompted.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Response and specify the location of the certificate response file saved in the previous step.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Once complete, the newly issued certificate will be in place. Click Close to complete the process.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Yes when prompted to restart the Mobility console.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Trusted Certificate

Opening the Mobility Console no longer produces a certificate error message with a certificate installed from a trusted CA.

Enabling Secure Remote Administration for the NetMotion Mobility Console

In addition, if you followed the guidance above and included the single-label hostname in the SAN field, accessing the server using the short name will also work without issue.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Summary

Always select the option to use HTTPS to ensure the highest level of security and protection of credentials when remotely administering a NetMotion Mobility gateway server. For optimal security and to provide the best user experience, use a certificate issued and managed by a trusted CA to prevent certificate errors when opening the Mobility console.

Additional Information

NetMotion Mobility as an Alternative to DirectAccess

NetMotion Mobility Device Tunnel Configuration

Comparing NetMotion Mobility and DirectAccess Part 1 – Security

Comparing NetMotion Mobility and DirectAccess Part 2 – Performance

DirectAccess and NetMotion Mobility Webinar

 

3 Comments
by Richard M. Hicks on February 1, 2018  •  Permalink
Posted in Encryption, NetMotion, NetMotion Mobility, Remote Access, Security, SSL and TLS, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on February 1, 2018

https://directaccess.richardhicks.com/2018/02/01/enabling-secure-remote-administration-for-the-netmotion-mobility-console/

KEMP LoadMaster Load Balancer Certificate Format Invalid

When implementing a KEMP LoadMaster load balancer, one of the first configuration tasks performed is importing root and intermediate Certification Authority (CA) certificates. When doing this, it is not uncommon to encounter the following error message.

Certificate Format Invalid.

KEMP LoadMaster Load Balancer Certificate Invalid

To resolve this issue, .CER files must first be converted to .PEM format before being imported in to the LoadMaster. Using OpenSSL, .CER files can quickly be converted to .PEM with the following command.

openssl x509 -inform der -in example.cer -out example.pem

Optionally, .CER files can be converted to .PEM online here.

If the root and/or intermediate certificates are from an internal PKI, export the certificates using the Base-64 encoded x.509 (.CER) option. Certificates exported using this format can be imported directly in to the LoadMaster without first having to be converted to .PEM.

KEMP LoadMaster Load Balancer Certificate Format Invalid

Pro tip: When entering the Certificate Name, it is not necessary to enter a file extension. The name will be appended with .PEM automatically upon import.

KEMP LoadMaster Load Balancer Certificate Format Invalid

KEMP LoadMaster Load Balancer Certificate Format Invalid

Additional Resources

DirectAccess Deployment Guide for KEMP LoadMaster Load Balancers

Maximize Your Investment in Windows 10 with KEMP LoadMaster Load Balancers

DirectAccess and the FREE KEMP LoadMaster Load Balancer

Configure KEMP LoadMaster Load Balancer for DirectAccess Network Location Server (NLS)

Planning and Implementing DirectAccess Video Training Course on Pluralsight

Implementing DirectAccess with Windows Server 2016 Book

1 Comment
by Richard M. Hicks on May 10, 2017  •  Permalink
Posted in ADC, application delivery controller, DirectAccess, High Availability, Kemp, Load Balancing, LoadMaster, SSL and TLS, troubleshooting, Windows 10, Windows 7, Windows 8, Windows 8.1, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on May 10, 2017

https://directaccess.richardhicks.com/2017/05/10/kemp-loadmaster-load-balancer-certificate-format-invalid/

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

A Windows 7 or Windows 8.x/10 client may fail to establish a DirectAccess connection using the IP-HTTPS IPv6 transition technology. When troubleshooting this issue, running ipconfig.exe shows that the media state for the tunnel adapter iphttpsinterface is Media disconnected.

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Running the Get-NetIPHttpsState PowerShell command on Windows 8.x/10 clients or the netsh interface httpstunnel show interface command on Windows 7 clients returns an error code of 0x90320, with an interface status Failed to connect to the IPHTTPS server; waiting to reconnect.

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Error code 0x90320 translates to SEC_I_INCOMPLETE_CREDENTIALS, indicating the client was unable to authenticate to the DirectAccess server during the TLS handshake when establishing the IP-HTTPS IPv6 transition tunnel. This occurs when the DirectAccess server or an Application Delivery Controller (ADC) is configured to perform client certificate authentication for IP-HTTPS connections. The client may fail to authenticate if it does not have a valid certificate issued by the organization’s internal certification authority (CA) or if the DirectAccess server or ADC is configured to perform IP-HTTPS client authentication incorrectly.

To resolve this issue, ensure that a valid certificate is installed on the DirectAccess client. In addition, ensure that the DirectAccess server or ADC is configured to use the correct CA when authenticating clients establishing IP-HTTPS connections.

Additional Information

DirectAccess IP-HTTPS Preauthentication 

DirectAccess IP-HTTPS Preauthentication using Citrix NetScaler

DirectAccess SSL Offload and IP-HTTPS preauthentication using Citrix NetScaler 

DirectAccess IP-HTTPS preauthentication using F5 BIG-IP 

SSL Certificate Considerations for DirectAccess IP-HTTPS 

3 Comments
by Richard M. Hicks on March 20, 2017  •  Permalink
Posted in ADC, application delivery controller, DirectAccess, IP-HTTPS, IPv6, IPv6 Transition, Netscaler, PowerShell, Remote Access, Security, SSL and TLS, troubleshooting, Windows 10, Windows 7, Windows 8, Windows 8.1, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on March 20, 2017

https://directaccess.richardhicks.com/2017/03/20/troubleshooting-directaccess-ip-https-error-code-0x90320/

DirectAccess IP-HTTPS Preauthentication using F5 BIG-IP

Note: For information about configuring the Citrix NetScaler to perform IP-HTTPS preauthentication, click here. For information about configuring Windows Server 2012 R2 to perform IP-HTTPS preauthentication natively, click here.

Introduction

DirectAccess IP-HTTPS Preauthentication using F5 BIG-IPRecently I wrote about security challenges with DirectAccess and the IP-HTTPS IPv6 transition technology. Specifically, IP-HTTPS transition tunnel connections are not authenticated by the DirectAccess server, only the client. This allows an unauthorized device to obtain an IPv6 address on the DirectAccess client network. With it, an attacker can perform network reconnaissance using ICMPv6 and potentially launch a variety of Denial-of-Service (DoS) attacks. For more details, click here.

Note: DirectAccess IPsec data connections not at risk. Data is never exposed at any time with the default configuration.

Mitigation

To mitigate these issues, it is recommended that an Application Delivery Controller (ADC) be used to terminate SSL connections and enforce client certificate authentication. Doing this will ensure that only authorized connections will be accepted by the DirectAccess server. In addition, there are some scalability and performance benefits to implementing this configuration when supporting Windows 7 clients.

Important Considerations

Performing IP-HTTPS preauthentication on the F5 BIG-IP is formally unsupported by Microsoft. In addition, terminating IP-HTTPS on the F5 appliance breaks OTP authentication.

F5 BIG-IP Configuration

To configure the F5 BIG-IP to perform SSL offload for DirectAccess IP-HTTPS, follow the guidance documented here. In addition, to configure the F5 BIG-IP to perform preauthentication for DirectAccess clients, when creating the client SSL profile, click Custom above the Client Authentication section and choose Require from the Client Certificate drop-down list and Always from the Frequency drop-down list. In addition, choose your internal PKI’s root Certification Authority (CA) certificate from the Trusted Certificate Authorities drop-down list and from the Advertised Certificate Authorities drop-down list.

DirectAccess IP-HTTPS Preauthentication using F5 BIG-IP

Summary

Enabling client certificate authentication for IP-HTTPS connections ensures that only authorized DirectAccess clients can establish a connection to the DirectAccess server and obtain an IPv6 address. It also prevents an unauthorized user from performing network reconnaissance or launching IPv6 Denial-of-Service (DoS) attacks.

13 Comments
by Richard M. Hicks on May 23, 2016  •  Permalink
Posted in ADC, application delivery controller, DirectAccess, Encryption, F5, IP-HTTPS, IPv6, IPv6 Transition, Load Balancing, Remote Access, Security, SSL and TLS, Windows 7, Windows Server 2012, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on May 23, 2016

https://directaccess.richardhicks.com/2016/05/23/directaccess-ip-https-preauthentication-using-f5-big-ip/

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Introduction

When preparing a DirectAccess server, an SSL certificate is required for the IP-HTTPS IPv6 transition technology. This certificate is often issued by a public Certification Authority (CA), but it can also be issued an organization’s internal Public Key Infrastructure (PKI).

SSL Certificate

Commonly an SSL certificate is issued for a single hostname, or subject. As long as the hostname matches the subject, everything works fine.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Multi-SAN SSL Certificate

To ease the management burden of using multiple certificates, or reduce the expense associated with using a wildcard certificate, organizations can request a multi-SAN (Subject Alternative Name) certificate, which matches more than one subject. The additional subjects are included in the Subject Alternative Name field on the SSL certificate.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS
A single multi-SAN certificate can be installed on multiple hosts and will work without issue as long as the hostname matches one of the SAN entries.

DirectAccess and Multi-SAN Certificates

When implementing DirectAccess in a multisite configuration, each entry point in the organization will have a unique public hostname. Instinctively, using a multi-SAN SSL certificate in this scenario would seem ideal.

Unfortunately, support for multi-SAN SSL certificates with DirectAccess is limited. To use a multi-SAN certificate for DirectAccess IP-HTTPS, the public hostname must match the name listed in the Subject field. In the example above, the subject is da.richardhicks.net, with SAN entries for da-west.richardhicks.net and da-east.richardhicks.net.

In this scenario, only the public name da.richardhicks.net is supported for use with DirectAccess. It will not work for any of the SAN entries. For example, attempting to configure DirectAccess to use this certificate with the public hostname da-west.richardhicks.net will fail with the following error message.

The subject name of certificate CN=[certificate subject name] is invalid.
Select a certificate with a valid subject name.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Attempting to work around this issue by using the Set-DAServer PowerShell cmdlet also fails to recognize the SSL certificate correctly.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Summary

Using a multi-SAN SSL certificate for the DirectAccess IP-HTTPS IPv6 transition technology is only supported when the public hostname matches the subject name of the certificate. Configuring DirectAccess with a public hostname listed in the SAN list is not supported. For multisite DirectAccess deployments, individual certificates must be issued for each entry point. Alternatively, a wildcard certificate can be used.

5 Comments
by Richard M. Hicks on March 28, 2016  •  Permalink
Posted in DirectAccess, IP-HTTPS, IPv6, IPv6 Transition, Remote Access, SSL and TLS, Windows 8, Windows 8.1, Windows Server 2012 R2, Windows Server 2016
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Posted by Richard M. Hicks on March 28, 2016

https://directaccess.richardhicks.com/2016/03/28/directaccess-and-multi-san-ssl-certificates-for-ip-https/

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