SSL and TLS Training for Always On VPN Administrators

Understanding Transport Layer Security (TLS) is essential for Always On VPN administrators. TLS (formerly Security Sockets Layer, or SSL) is used not only for Secure Socket Tunneling Protocol (SSTP), the protocol of choice for the Always On VPN user tunnel in most deployments, but many other technologies such as secure websites and email, Remote Desktop Protocol (RDP), secure LDAP (LDAPS), and many more. High-quality, affordable TLS training is challenging to find, however.

UPDATE! This course has been further discounted for a limited time. Details below!

Practical TLS

Thankfully, Ed Harmoush from Practical Networking has a fantastic training course called Practical TLS that meets these requirements. It is the most comprehensive TLS training course I’ve seen and is surprisingly affordable too!

Course Content

The Practical TLS training course includes the following modules.

  • Module 1 – SSL/TLS Overview (free preview!)
  • Module 2 – Cryptography
  • Module 3 – x509 Certificates and Keys
  • Module 4 – Security through Certificates
  • Module 5 – Cipher Suites
  • Module 6 – SSL/TLS Handshake
  • Module 7 – TLS Defenses

TLS 1.3

The Practical TLS training course does not yet include a module on the newest TLS protocol, TLS 1.3. However, it is due out imminently! Ed is working on the content as we speak, and a preview module is included in the course today. Look for the final TLS 1.3 module soon.

Bonus Content

In addition to excellent TLS training, the course includes free OpenSSL training! Administrators working with certificates in non-Microsoft environments are sure to find this helpful. Understanding OpenSSL will benefit administrators working with network and security appliances such as firewalls and load balancers.

Enroll Now

The cost of the Practical TLS training course is regularly $297.00. It is a perpetual license, so you can view the content whenever you like and as often as you wish. You will also have access to future updates, such as the upcoming TLS 1.3 module. In addition, you can save $100.00 on the course by using promotional code RICHARDHICKS when you sign up. Don’t hesitate. Register for Practical TLS training now!

Special Discount

For a limited time, you can use the code PracticalTLS13 to get this entire course for just $49.00! This won’t last long, so register soon!

Additional Information

Practical Networking Blog

Practical TLS Training Course – $100 Off!

OpenSSL Training Course

Microsoft Always On VPN and TLS 1.3

Microsoft Always On VPN SSTP Security Configuration

Microsoft Always On VPN SSTP Certificate Renewal

Microsoft Always On VPN SSTP with Let’s Encrypt Certificates

SSL Certificate Considerations for DirectAccess IP-HTTPS

SSL Certificate Considerations for DirectAccess IP-HTTPSDirectAccess uses IPv6 exclusively for communication between the client and server. IPv6 transition technologies are used to support DirectAccess communication over the IPv4 public Internet. One of those IPv6 transition technologies, IP-HTTPS, uses HTTP for encapsulation and SSL/TLS for authentication of the DirectAccess server.

SSL Certificates

When configuring DirectAccess, an SSL certificate must be provided for IP-HTTPS. There are three different types of SSL certificates that can be used.

Public SSL Certificate – Using an SSL certificate signed by a public certification authority (CA) is the recommended best practice for configuring DirectAccess IP-HTTPS. This provides the highest level of assurance for DirectAccess clients connecting via IP-HTTPS.

Private SSL Certificate – Using an SSL certificate issued by the organization’s internal CA is an acceptable alternative to using a public SSL certificate in most cases. This can reduce the cost associated with obtaining the certificate, especially for multisite deployments.

Self-Signed Certificate – Using a self-signed certificate is not recommended and should be avoided in most deployment scenarios. A self-signed certificate provides no real assurance for DirectAccess clients. Crucially, using a self-signed certificate will disable support for null SSL and TLS cipher suites. This reduces the overall scalability and performance of the remote access solution.

SSL Certificate Considerations for DirectAccess IP-HTTPS

Figure 1. Null cipher suites not supported when using a self-signed SSL certificate for IP-HTTPS.

Certificate Requirements

The SSL certificate must include the Server Authentication ( Enhanced Key Usage (EKU) Object Identifier (OID). It should use an RSA key of 2048 bits and be signed with SHA256. Using stronger keys provides no additional protection and should not be used. In addition, SSL certificates using ECDSA keys is not recommended, as they do not support null cipher suites.


In most cases, using a public SSL certificate is ideal. However, issuing a certificate from a private CA is also acceptable. Using self-signed certificates can be used for non-production testing and in very small production deployments, but should generally be avoided.

Additional Resources

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

DirectAccess and the TLS Logjam Attack

Another critical flaw affecting Transport Layer Security (TLS) was discovered recently that could put some organizations at risk. The “Logjam” attack exploits a weakness in how the Diffie-Hellman key exchange is used. An attacker, acting as a man-in-the-middle, can potentially force a downgrade of the TLS connection, resulting in the use of weak cryptography. The Qualys SSL Labs SSL Server Test has been updated to identify this vulnerability. When testing a DirectAccess server you will receive the following warning message.

“This server supports weak Diffie-Hellman (DH) key exchange parameters. Grade capped to B.”

DirectAccess and the Logjam Attack

DirectAccess leverages SSL and TLS as part of the IP-HTTPS IPv6 transition protocol, which is used to tunnel IPv6 packets over the IPv4 Internet. These IPv6 packets are encrypted using IPsec. If an attacker were to break the SSL/TLS connection they would gain nothing. Because of this, a dedicated DirectAccess server is unaffected by the Logjam attack. Mitigating it would provide no additional protection, so you can safely ignore the warning about weak DH key exchange parameters being supported.

However, if DirectAccess has been configured to use one-time password (OTP) authentication, the client-based VPN role has been enabled and configured, or the Web Application Proxy (WAP) role has been installed on the DirectAccess server, then the Logjam attack represents a serious risk and should be mitigated. Also, in some cases it may be desirable to make this change on a dedicated DirectAccess server just to prevent an audit finding and avoid having to explain why the DirectAccess workload would be unaffected by this attack.

To mitigate this vulnerability it will be necessary to remove support for cipher suites that use the Diffie-Hellman key exchange protocol on the DirectAccess server. This is accomplished by opening the Local Group Policy Editor (gpedit.msc) on the DirectAccess server and expanding Computer Configuration, Administrative Templates, and Network. Select SSL Configuration Settings and then double-click SSL Cipher Suite Order. Select Enabled and then replace the default list of cipher suites with the following list.


DirectAccess and the Logjam Attack

Once complete, restart the DirectAccess server. The Qualys SSL Labs server test should no longer give a warning about the use of weak Diffie-Hellman keys. In addition, this reordering and optimization of cipher suites will also improve the protocol support and key exchange scores, as shown here.

DirectAccess and the Logjam Attack

As a reminder, and overall rating of “F” is expected when testing a dedicated DirectAccess server. By design, DirectAccess provides support for null cipher suites to improve scalability and performance for Windows 8.x and later DirectAccess clients. More details here.

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