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

Always On VPN IKEv2 Load Balancing and NAT

Always On VPN IKEv2 Load Balancing and NATOver the last few weeks, I’ve worked with numerous organizations and individuals troubleshooting connectivity and performance issues associated with Windows 10 Always On VPN, and specifically connections using the Internet Key Exchange version 2 (IKEv2) VPN protocol. An issue that appears with some regularity is when Windows 10 clients fail to connect with error 809. In this scenario, the server will accept connections without issue for a period of time and then suddenly stop accepting requests. When this happens, existing connections continue to work without issue in most cases. Frequently this occurs with Windows Server Routing and Remote Access Service (RRAS) servers configured in a clustered array behind an External Load Balancer (ELB).

Network Address Translation

It is not uncommon to use Network Address Translation (NAT) when configuring Always On VPN. In fact, for most deployments the public IP address for the VPN server resides not on the VPN server, but on an edge firewall or load balancer connected directly to the Internet. The firewall/load balancer is then configured to translate the destination address to the private IP address assigned to the VPN server in the perimeter/DMZ or the internal network. This is known a Destination NAT (DNAT). Using this configuration, the client’s original source IP address is left intact. This configuration presents no issues for Always On VPN.

Source Address Translation

When troubleshooting these issues, the common denominator seems to be the use of Full NAT, which includes translating the source address in addition to the destination. This results in VPN client requests arriving at the VPN server as appearing not to come from the client’s original IP address, but the IP address of the network device (firewall or load balancer) that is translating the request. Full NAT may be explicitly configured by an administrator, or in the case of many load balancers, configured implicitly because the load balancer is effectively proxying the connection.

Known Issues

IKEv2 VPN connections use IPsec for encryption, and by default, Windows limits the number of IPsec Security Associations (SAs) coming from a single IP address. When a NAT device is performing destination/full NAT, the VPN server sees all inbound IKEv2 VPN requests as coming from the same IP address. When this happens, clients connecting using IKEv2 may fail to connect, most commonly when the server is under moderate to heavy load.

Resolution

The way to resolve this issue is to ensure that any load balancers or NAT devices are not translating the source address but are performing destination NAT only. The following is configuration guidance for F5, Citrix ADC (formerly NetScaler), and Kemp load balancers.

F5

On the F5 BIG-IP load balancer, navigate to the Properties > Configuration page of the IKEv2 UDP 500 virtual server and choose None from the Source Address Translation drop-down list. Repeat this step for the IKEv2 UDP 4500 virtual server.

Always On VPN IKEv2 Load Balancing and NAT

Citrix ADC

On the Citrix ADC load balancer, navigate to System > Settings > Configure Modes and check the option to Use Subnet IP.

Always On VPN IKEv2 Load Balancing and NAT

Next, navigate to Traffic Management > Load Balancing > Service Groups and select the IKEv2 UDP 500 service group. In the Settings section click edit and select Use Client IP. Repeat these steps for the IKEv2 UDP 4500 service group.

Always On VPN IKEv2 Load Balancing and NAT

Kemp

On the Kemp LoadMaster load balancer, navigate to Virtual Services > View/Modify Services and click Modify on the IKEv2 UDP 500 virtual service. Expand Standard Options and select Transparency. Repeat this step for the IKEv2 UDP 4500 virtual service.

Always On VPN IKEv2 Load Balancing and NAT

Caveat

Making the changes above may introduce routing issues in your environment. When configuring these settings, it may be necessary to configure the VPN server’s default gateway to use the load balancer to ensure proper routing. If this is not possible, consider implementing the workaround below.

Workaround

To fully resolve this issue the above changes should be made to ensure the VPN server can see the client’s original source IP address. If that’s not possible for any reason, the following registry key can be configured to increase the number of established SAs from a single IP address. Be advised this is only a partial workaround and may not fully eliminate failed IKEv2 connections. There are other settings in Windows that can prevent multiple connections from a single IP address which are not adjustable at this time.

To implement this registry change, open an elevated PowerShell command window on the RRAS server and run the following commands. Repeat these commands on all RRAS servers in the organization.

New-ItemProperty -Path ‘HKLM:SYSTEM\CurrentControlSet\Services\IKEEXT\Parameters\’ -Name IkeNumEstablishedForInitialQuery -PropertyType DWORD -Value 50000 -Force

Restart-Service IKEEXT -Force -PassThru

Additional Information

IPsec Traffic May Be Blocked When A Computer is Behind a Load Balancer

Windows 10 Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Windows 10 Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Always On VPN SSTP Load Balancing with Citrix NetScaler ADCThe Internet Key Exchange version 2 (IKEv2) VPN protocol is the protocol of choice when the highest level of security is required for Always On VPN connections. It uses IPsec and features configurable security parameters that allow administrators to adjust policies to meet their specific security requirements. IKEv2 is not without some important limitations, but organizations may insist on the use of IKEv2 to provide the greatest protection possible for remote connected clients. Due to complexities of the IKEv2 transport, special configuration on the Citrix ADC (formerly NetScaler) is required when load balancing this workload.

Special Note: In December 2019 a serious security vulnerability was discovered on the Citrix ADC that gives an unauthenticated attacker the ability to arbitrarily execute code on the appliance. As of this writing a fix is not available (due end of January 2020) but a temporary workaround can be found here.

Load Balancing IKEv2

When an Always On VPN client establishes a connection using IKEv2, communication begins on UDP port 500, but switches to UDP port 4500 if Network Address Translation (NAT) is detected in the communication path between the client and the server. Because UDP is connectionless, custom configuration is required to ensure that VPN clients maintain connectivity to the same backend VPN server during this transition.

Initial Configuration

Load balancing IKEv2 using the Citrix ADC is similar to other workloads. Below are specific settings and parameters required to load balance IKEv2 using the Citrix ADC.

Note: This article is not a comprehensive configuration guide for the Citrix ADC. It assumes the administrator is familiar with basic load balancing concepts and has experience configuring the Citrix ADC.

Service Settings

The load balancing services for IKEv2 VPN will use UDP ports 500 and 4500. Create the service group and assign group members for UDP 500 as follows.

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Repeat the steps above to create the service group for UDP port 4500.

Virtual Server Settings

Two virtual servers are required, one for UDP port 500 and one for UDP port 4500. Ensure that the service group using UDP port 500 is bound to the virtual server using the same port.

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Repeat the steps above to create the virtual service for UDP port 4500.

Service Monitoring

Since IKEv2 uses the UDP protocol, the only option for service monitoring is to use PING, which is configured by default. Ensure that the firewall on the VPN server allows inbound ICMPv4 and ICMPv6 Echo Request. The default PING monitor on the Citrix ADC will ping the resource every 5 seconds. If a different interval is required, the administrator can edit the PING monitor and bind that to the service or service group as necessary.

Persistency Group

A Persistency Group on the Citrix ADC will be configured to ensure that IKEv2 VPN client requests from the same client are always routed to the same backend server. Follow the steps below to create a Persistency Group and assign it to both IKEv2 virtual servers created previously.

  1. In the Citrix ADC management console expand Traffic Management > Load Balancing > Persistency Groups.
  2. Click Add.
  3. Enter a descriptive name for the Persistency Group.
  4. Select SOURCEIP from the Persistence drop-down list.
  5. Next to the Virtual Server Name section click the Add button.
  6. Add both previously configured IKEv2 virtual servers for UDP 500 and 4500.
  7. Click Create.

Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Use Client IP

To ensure reliable connectivity for IKEv2 VPN connections it is necessary for the VPN server to see the client’s original source IP address. Follow the steps below to configure the Service Group to forward the client’s IP address to the VPN server.

  1. In the Citrix ADC management console expand System, click Settings, and then click Configure Modes.
  2. Select Use Subnet IP.
  3. Click Ok.Always On VPN IKEv2 Load Balancing and NAT
  4. Expand Traffic Management, click Load Balancing, and then click Service Groups.
  5. Select the IKEv2 UDP 500 Service Group.
  6. Click Edit in the Settings section.
  7. Select Use Client IP.
  8. Repeat these steps on the IKEv2 UDP 4500 Service Group.Always On VPN IKEv2 Load Balancing and NAT

Note: Making the above changes will require configuring the VPN server to use the Citrix ADC as its default gateway.

Additional Information

Windows 10 Always On VPN IKEv2 Load Balancing and NAT

Windows 10 Always On VPN SSTP Load Balancing with Citrix NetScaler ADC

Windows 10 Always On VPN IKEv2 Features and Limitations

Windows 10 AlWAYS On VPN and IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Certificate Requirements for IKEv2