Webinar: Certificate Automation in Practice – A Technical Deep Dive

If you manage Windows Server workloads that require public TLS certificates like Always On VPN, DirectAccess, Remote Desktop Gateway, Internet Information Services (IIS), and others, you know that certificate expirations don’t send friendly reminders. Certificates expire quietly. Too often, end users are the ones who sound the alarm—when resources are already unavailable. Of course, this never happens at a convenient time. It’s usually the middle of the night, on the weekend.

Current State

Most Windows IT teams are still managing certificates the same way they did years ago, using spreadsheets, calendar reminders, and an assortment of renewal scripts. It usually works… until it suddenly doesn’t.

Free Webinar

I’m pleased to announce that I’ll be joining Todd Gardner from CertKit for a free live webinar on Tuesday, June 16, at 11:00 AM CDT, in which we will break down the following:

  • Why certificate mismanagement causes so much pain at scale
  • How to build real automation that works across your full environment, including internal services and vendor appliances
  • A live demonstration of CertKit showing end-to-end discovery, monitoring, and automated renewal

There will also be time for live Q&A, so bring your questions!

Join Us!

If you’re tired of patching the problem with fragile scripts and assorted reminders, join us to learn about a fully automated solution that can dramatically improve the situation. Register now and don’t miss this opportunity to reduce your TLS certificate management burden and end the need for 2 AM certificate renewal fire drills.

Webinar Details

Webinar: TLS Certificate Automation for Windows Infrastructure
Hosts: Todd Gardner (CertKit) and Richard Hicks (Richard M. Hicks Consulting, Inc.)
Date: Tuesday, June 16
Time: 11:00 AM CDT
Registration: Click here to register!

Recording

If you are unable to attend the live session, be sure to register to receive a link to the recorded session for on-demand viewing.

Leave a comment
by Richard M. Hicks on June 5, 2026  •  Permalink
Posted in Automation, Certificate Authentication, Certificate Lifecycle Management, Certificate Services, certificates, CertKit, CLM, Microsoft, SSL and TLS, TLS, Windows 10, Windows 11, Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025
Tagged , , , , , , , , , , , , , , , , , ,

Posted by Richard M. Hicks on June 5, 2026

https://directaccess.richardhicks.com/2026/06/05/webinar-certificate-automation-in-practice-a-technical-deep-dive/

What’s New in Entra Global Secure Access Client v2.31.125

On June 2, 2026, Microsoft released version 2.31.125 of the Entra Global Secure Access (GSA) client. This update introduces several enhancements designed to improve client resiliency, simplify troubleshooting, and provide administrators with better visibility into network connection status.

Changes in v2.31.125

GSA client v2.31.125 includes new features to streamline connectivity troubleshooting.

Network Status

The new GSA client can now distinguish between a complete network disconnection and a scenario where the device remains connected to a local network but lacks internet access. This distinction helps administrators and users more quickly identify the source of connectivity issues and reduce troubleshooting time.

Network Disconnected

No Internet Connectivity

Local Access

When Intelligent Local Access (ILA) is enabled, the client now clearly indicates when a device is connected to a trusted private network. This provides additional visibility into ILA decision-making and helps confirm that local access policies are functioning as expected.

Sign Out

The new GSA client includes an account picker when a user signs out on Entra-registered or Entra-joined devices. This enhancement simplifies account management on shared or multi-user devices by allowing users to switch identities without fully reinstalling or reconfiguring the client.

The sign out option is disabled by default. It must be enabled by setting the following registry key.

HKLM\Software\Microsoft\Global Secure Access Client\HideSignOutButton DWORD = 0

User Session Detection

Because the GSA client supports only a single interactive Windows session, this new indicator helps quickly identify unsupported multi-session scenarios that may impact client functionality or troubleshooting efforts.

Other Changes

In addition to the new features and capabilities outlined above, these changes are also included.

  • Updated embedded .NET Runtime to version 8.0.26.
  • GSA Forwarding Profile Service now automatically restarts after a failure.
  • Improved detection and tunneling of agentic network connections.
  • Various bug fixes and performance improvements.

Summary

GSA Client v2.31.125 introduces several useful enhancements focused on troubleshooting, resiliency, and user experience. Improved network status visibility, Intelligent Local Access awareness, account sign-out support, and enhanced session detection provide administrators with better diagnostic capabilities while making the client easier for end users to understand and manage. Although this release remains in preview, administrators are encouraged to begin testing this latest release soon.

Additional Information

Microsoft Entra Global Secure Access (GSA) Client v2.31.125

Microsoft Entra Private Access Intelligent Local Access

Leave a comment
by Richard M. Hicks on June 4, 2026  •  Permalink
Posted in administration, Azure Active Directory, Azure AD, Azure AD Join, cloud, Cloud Service, Deployment, Device Management, Enterprise, enterprise mobility, Entra, Entra Global Secure Access, Entra ID, Entra Internet Access, Entra Private Access, Global Secure Access, GSA, Hybrid Azure AD Join, Hybrid Entra ID Join, Hybrid Entra Join, ILA, Intelligent Local Access, Microsoft, Microsoft Entra, Microsoft Entra Global Secure Access, Microsoft Entra ID, Microsoft Entra Internet Access, Microsoft Entra Private Access, Mobility, Operational Support, Remote Access, SASE, Secure Access Service Edge, Security, Security Service Edge, Windows 10, Windows 11, Zero Trust, Zero Trust Network Access, ZTNA
Tagged , , , , , , , , , , , , , ,

Posted by Richard M. Hicks on June 4, 2026

https://directaccess.richardhicks.com/2026/06/04/whats-new-in-entra-global-secure-access-client-v2-31-125/

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

With just over six months remaining before Windows Server 2016 reaches end of support, now is the time to begin planning migrations for workloads hosted on this platform. Mainstream support ended on January 11, 2022, and Windows Server 2016 has since remained in extended support. However, extended support ends on January 12, 2027. After that date, Microsoft will no longer provide security updates or technical support, increasing the risk of running production workloads due to exposure to newly discovered vulnerabilities and 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 September 1-3, 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

Leave a comment
by Richard M. Hicks on June 1, 2026  •  Permalink
Posted in Active Directory Certificate Services, AD CS, ADCS, authentication, CBA, Certificate Authentication, Certificate Authority, Certificate Connector for Intune, Certificate Services, Certificate-Based Authentication, certificates, Consulting Services, Cryptography, Encryption, end of life, Enterprise, Entra Certificate-Based Authentication, EOL, Infrastructure, Intune, Intune Certificate Connector, Intune PFX Connector, Microsoft, Microsoft Intune, NDES, Network Device Enrollment Service, Network Device Enrollment Services, Operational Support, PFX Connector, PKCS, PKI, Professional Services, public key infrastructure, SCEP, Security, Simple Certificate Enrollment Protocol, Update, Windows 10, Windows 11, Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025
Tagged , , , , , , , , , , , , , , , , ,

Posted by Richard M. Hicks on June 1, 2026

https://directaccess.richardhicks.com/2026/06/01/reminder-windows-server-2016-end-of-life-january-2027-plan-your-ad-cs-migration-now/

« Older Posts