Webinar: Certificate Automation for Windows Infrastructure

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, May 26, 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, May 26
Time: 11:00 AM CDT
Registration: Click here to register!

Always On VPN with PEAP Fails in Windows 11 26H1

Always On VPN RasMan Errors in Windows 10 1903

There appears to be a bug in the latest Windows 11 26H1 (no, that’s not a typo – 26H1) build affecting Protected Extensible Authentication Protocol (PEAP). In my testing, all VPN connection attempts (Always On VPN and manual/ad-hoc) failed when PEAP was used for authentication.

Windows 11 26H1

Recently, while reviewing downloads and product keys in Visual Studio, I noticed a new Windows 11 release listed: Windows 11 26H1 (business and consumer editions). I initially thought 26H1 would be ARM-only, but the download is available for x64 as well.

I’m not sure whether this is intended as a general release, because Microsoft describes it as an Insider Experimental Preview Build (28200.1873). I also don’t recall seeing Insider builds offered through Visual Studio downloads, so I’m not sure what to make of it. Either way, if you’re evaluating this build, the notes below document a VPN issue I was able to reproduce.

Troubleshooting

After preparing a Windows 11 26H1 test client, I found that the Always On VPN user tunnel would not connect. The same configuration worked on earlier Windows 11 versions. In the event log, I observed the following errors.

Error 619

When using SSTP, the event log records error code 619 (event ID 20227) from the RasClient event source, with the following error message.

The user [domain\user] dialed a connection named [connection name] which has failed. The error code returned on failure is 619.

Error 691

When using IKEv2, the event log records error code 691 (event ID 20227) from the RasClient event source, with the following error message.

The user [domain\user] dialed a connection named [connection name] which has failed. The error code returned on failure is 691.

Workaround

At the time of writing, the only workaround I’ve found to restore Always On VPN connectivity is to switch authentication from PEAP to EAP-TLS. This may not be a drop-in change for every environment, so evaluate the security and operational impact before rolling it out broadly. You’ll need to enable EAP-TLS on both the client and the NPS/RADIUS server.

Summary

I’m not convinced Windows 11 26H1 will be widely deployed soon, since it appears to be an experimental/Insider build rather than a general release. If you decide to evaluate it, plan to use the workaround above to maintain Always On VPN connectivity.

Feedback

Have you tested Always On VPN with Windows 11 26H1? If so, do you see the same behavior? Share your findings in the comments.

Additional Information

Windows 11 Insider Experimental (26H1) Preview Build 28200.1873

Entra Private Access and VPN Migration Strategies on Entra.News

I recently had the opportunity to connect with Merill Fernando from Microsoft as a guest on his popular Entra.News podcast to discuss Microsoft Entra Private Access, which is part of the Entra Global Secure Access Security Service Edge (SSE) service. We spent the hour talking about the similarities and differences between classic VPN technologies and zero-trust network access (ZTNA). In addition, we discussed some technical aspects of Entra Private Access, and I shared migration and coexistence strategies to help ease the transition to zero trust. Also, we discussed the importance of integrating Entra Conditional Access and the shift from network to application access. You’ll find the interview at Entra.News and also on YouTube. Enjoy!

Additional Information

How to Migrate from Legacy VPN to Entra Private Access – Entra.News

Microsoft Entra Private Access

Always On VPN vs. Entra Private Access

Microsoft Entra Private Access Network Connector Overview and Deployment Strategies

Microsoft Entra Private Access Intelligent Local Access