Windows Server 2016 End of Life January 2027: Plan Your AD CS Migration Now

Happy New Year, everyone! As the calendar rolls over to 2026, it’s time to start planning the migration of workloads hosted on Windows Server 2016. Mainstream support ended for Windows Server 2016 on January 11, 2022, after which it entered extended support. However, extended support for Windows Server 2016 ends on January 12, 2027, at which point it will be end of life and no longer supported. Running production workloads on Windows Server 2016 beyond this date exposes organizations to significant security risk, as it no longer receives security updates, leaving these systems vulnerable to exploits.

Active Directory Certificate Services

Many organizations are still running critical infrastructure on Windows Server 2016. Administrators often delay upgrading Microsoft Active Directory Certificate Services (AD CS) due to its complexity. However, a well-planned AD CS migration not only reduces risk but also provides an opportunity to modernize cryptography, certificate templates, and operational practices.

Certificate Authorities

Administrators must carefully migrate Certificate Authorities (CAs) running on Windows Server 2016 to minimize downtime. In environments where ongoing CA maintenance has been limited, migrating the CA database can be especially challenging. If the CA is installed on a domain controller, now is a good time to consider separating these services to ensure reliable operation. Also, it’s a good idea to evaluate the CA’s configuration and security posture during migration to enhance security and improve service resilience.

NDES Servers

Microsoft Network Device Enrollment Services (NDES) servers, commonly deployed to facilitate certificate enrollment via Microsoft Intune, pose a unique challenge during migration. Unfortunately, configuring NDES is exceedingly complex and error-prone. NDES relies on a delicate combination of specialized IIS configuration, AD service accounts, custom certificate templates, and CA permissions, making even minor changes risky without proper planning. Not surprisingly, administrators are often hesitant to touch these systems as they are notoriously difficult to troubleshoot when problems arise.

Pro Tip: We spend an entire day covering NDES configuration in the Mastering Enterprise PKI Certificates with Microsoft Intune training course. The next session is March 10-12, 2026. Register now!

Intune Certificate Connectors

Don’t overlook Windows Server 2016 servers with the Intune Certificate Connector installed. Fortunately, this is one of the more manageable workloads to migrate. All that’s required is to install new connectors on supported servers and delete the old ones.

Summary

With extended support for Windows Server 2016 ending on January 12, 2027, organizations running production workloads—especially critical infrastructure such as Active Directory Certificate Services (AD CS), Certificate Authorities (CAs), and NDES servers—face significant security risks from unpatched vulnerabilities once the OS reaches end-of-life. Careful migration planning to newer versions such as Windows Server 2022 or 2025 is essential to minimize downtime, improve security posture, and ensure long-term resilience.

Start Planning Now

Don’t leave these mission-critical infrastructure services to the last minute! Begin planning your migration today. If you’d like expert guidance, I have many years of experience migrating these workloads. I have developed specialized tools and techniques to ensure a smooth, secure, and successful transition. Fill out the form below to schedule a free one-hour consultation to assess your Windows Server 2016 AD CS workloads, identify migration risks, and outline next steps.

Additional Information

Windows Server 2016 Lifecycle Policy

PKI Fundamentals with Microsoft Active Directory Certificate Services (AD CS) Online Training Course

Mastering Enterprise PKI Certificates with Microsoft Intune Online Training Course

Preventing Port Exhaustion on Entra Private Network Connector Servers

Microsoft Entra Private Access is a powerful zero-trust network access solution that is remarkably simple to install and configure. Administrators can quickly install the Global Secure Access (GSA) agent on their endpoints, then install the Entra Private Network Connector to enable secure remote access to private, internal resources. However, the ease with which Entra Private Access can be configured can potentially lead to connectivity issues in some scenarios. This post demonstrates how to diagnose port exhaustion issues and expand the available port range to address them.

Entra Private Network Connector

The Entra Private Network Connector is a key component of the Entra Private Access solution. The Private Network Connector is essentially the old Azure Application Proxy, enhanced to support TCP and UDP applications in addition to HTTP-based web applications. It is installed on an on-premises Windows server to provide GSA clients with access to internal data and applications.

Network Connectivity

The GSA client is not a virtual network adapter like most traditional VPN clients. Instead, the GSA client installed on the client operates as a filter driver in the network stack, selectively intercepting traffic and tunneling it over the GSA tunnel based on configured policy. As such, it does not appear as a network adapter in the operating system and does not have its own IP address.

Translation

When traffic from the GSA client is routed over the Entra Private Network Connector, the traffic egressing from the connector server to the internal network is effectively translated. That is, the source IP address of traffic destined for an internal resource is the connector server’s IP address, not the client’s original source IP address.

Port Exhaustion

The ephemeral port range on Windows servers spans from 49152 to 65535, leaving only 16,384 ports available. This can easily be exhausted when many clients are connected to a single Entra Private Network Connector server. This pool can also be depleted by poorly written or badly behaving applications that needlessly open many socket connections to internal resources.

Troubleshooting

Administrators can view the ephemeral port configuration for both TCP and UDP by running the following commands.

netsh.exe interface ipv4 show dynamicportrange protocol=tcp

netsh.exe interface ipv4 show dynamicportrange protocol=udp

To determine if port exhaustion is an issue, open an elevated PowerShell command window and run the following command.

Get-NetTcpConnection | Where-Object State -match ‘established’ | Measure-Object

Next, run the following PowerShell command to identify the number of ports consumed exclusively by the Entra Private Network Connector.

$ProcessId = Get-CimInstance -ClassName win32_service | Where-Object Name -eq ‘WAPCSvc’ | Select-Object -ExpandProperty ProcessID

Get-NetTCPConnection | Where-Object { $_.State -match ‘established’ -and $_.OwningProcess -eq $ProcessId } | Measure-Object

If the number of ports consumed by the Entra Private Network Connector approaches the upper limit of available ports, administrators should increase the ephemeral port range to ensure the connector server operates reliably.

Note: Use the Get-NetUdpEndpoint PowerShell command to monitor UDP port consumption on Entra Private Network Connector servers.

Resolution

To increase the ephemeral port range on the Entra Private Network Connector server, open an elevated command window and run the following commands.

netsh.exe interface ipv4 set dynamicportrange protocol=tcp startport=10000 numberofports=55535
netsh.exe interface ipv4 set dynamicportrange protocol=udp startport=10000 numberofports=55535
netsh.exe interface ipv6 set dynamicportrange protocol=tcp startport=10000 numberofports=55535
netsh.exe interface ipv6 set dynamicportrange protocol=udp startport=10000 numberofports=55535

Running these commands will increase the number of available ephemeral ports on the server to more than 50,000, well above the default. In most cases, this should be sufficient to handle many GSA client connections. However, administrators are cautioned to monitor port usage on the Entra Private Network Connector servers to ensure continued reliable operation. It may be necessary to deploy additional connector servers to process the existing workload.

Summary

Entra Private Network Connectors can exhaust the default 16,384-port ephemeral range when many GSA clients access internal TCP/UDP resources. Administrators can diagnose the issue by filtering Get-NetTCPConnection results by the WAPCSvc process, then expanding the range to over 50,000 ports using netsh.exe, as shown above. Monitor usage continuously in high-load environments to ensure consistent and stable access. And if you find you need more than 50,000 ports per server, it’s probably time to deploy additional connector servers. 😊

Additional Information

Microsoft Entra Private Access

Entra Private Access Channels are Unreachable

Microsoft Entra private network connectors

PKI Fundamentals with Microsoft AD CS Training Course

I’m excited to announce that I’ve partnered once again with the fine folks at the ViaMonstra Online Academy to deliver a new live training course entitled PKI Fundamentals with Microsoft Active Directory Certificate Services (AD CS). The event consists of six weekly live webinars beginning on Thursday, January 15, 2026, at 3:00 PM CST.

Why AD CS Training?

Digital certificates are strong, phishing-resistant credentials that are an excellent choice for authentication to critical workloads like Always On VPN and enterprise Wi-Fi. However, managing certificate services infrastructure can be daunting. This course provides administrators with a fundamental understanding of enterprise PKI with Microsoft AD CS.

Course Overview

The event format for this course consists of six weekly live sessions on Thursdays starting on January 15, 2026. The classes are two hours long, running from 3:00 PM CST to 5:00 PM CST each day. During the course, we’ll cover the following topics.

  • PKI concepts and certificate use cases
  • Designing and deploying certificate authorities (CAs)
  • Configuring templates and enrollment
  • Managing revocation and maintenance

Who Should Attend

Organizations planning to use certificate authentication for enterprise VPN and Wi-Fi workloads will benefit from this training course. Also, those considering a new AD CS deployment will find this training beneficial. In addition, administrators managing an existing production AD CS environment will gain valuable insight.

Enroll Now

Registration for this training class is available now. The cost is $295.00—an incredible bargain! Don’t miss out on this fantastic opportunity to gain foundational AD CS skills. Click the registration link below and reserve your spot today!

Additional Information

Public Key Infrastructure (PKI)

Enterprise PKI

Cloud PKI for Microsoft Intune