The Case for 6-Day Public TLS Certificates

In February 2025, Let’s Encrypt introduced the option to enroll for public TLS certificates with a 6-day validity period.  This represents a significant shift toward short-lived certificates and aligns with the broader industry trend of reducing certificate lifetimes to improve security. While this may seem aggressive at first glance, organizations that have embraced automation will find that extremely short-lived certificates offer compelling security and operational advantages in some scenarios.

Benefits

Extremely short-lived TLS certificates offer several important security and operational benefits, particularly for organizations that have already embraced automation for certificate lifecycle management. Key advantages include:

  • Minimized Risk of Key Compromise – 6-day certificates dramatically reduce the exposure window of private key compromise events, giving attackers a limited window of opportunity to exploit key access.
  • Automation Validation – Short-lived certificates force organizations to adopt and validate automated enrollment and renewal processes, ensuring that certificate lifecycle management is reliable and resilient.
  • IP Address Support – 6-day TLS certificates from Let’s Encrypt support IP addresses, allowing administrators to secure workloads that do not have entries in DNS.

Use Cases

6-day TLS certificates are well-suited for a range of modern workloads, especially those that benefit from frequent key rotation, automation, and dynamic provisioning. 6-Day TLS certificates are well-suited for the following workloads:

  • High Value Resources – Using 6-day TLS certificates is beneficial for high-security or sensitive workloads where frequent key rotation is desired.
  • Test Labs – High-frequency certificate rotation allows for thorough testing of automation processes to ensure operational reliability of production deployments. Rapid iteration of 6-day TLS certificates allows administrators to identify potential issues and implement changes before long-term certificates expire.
  • Ephemeral Infrastructure – 6-day TLS certificates work well with dynamic workloads such as containers, where environments are rapidly provisioned and destroyed. These hosts might only live for a few hours or days, making short-lived certificates an ideal choice in this scenario.
  • Workload Bootstrapping – 6-day TLS certificates can be used where a certificate is required only to perform initial configuration. For example, an IP-based TLS certificate can be used to configure TLS services, then later migrated to a long-term certificate when DNS is configured and the service is placed into production.

Enterprise Usage

Administrators will find that 6-day public TLS certificates work well with many popular Windows Server workloads. Here are a few examples.

  • Always On VPN – Enterprise secure remote access is a popular target for attackers because the service is exposed to the Internet. Using 6-day TLS certificates ensures frequent key rotation, reducing exposure to key compromise.
  • Remote Desktop Services – Many organizations continue to use Remote Desktop Gateway to provide access to on-premises applications, another workload that is exposed to the Internet. Using 6-day TLS certificates is equally effective in this scenario.

What About DirectAccess?

Although DirectAccess would be another ideal Windows Server workload for 6-day TLS certificates, my testing shows that it does not work. The root cause is that 6-day TLS certificates from Let’s Encrypt do NOT include subject information (the field is blank). Unfortunately, because of the way in which DirectAccess validates this certificate, it requires information in this field. More details can be found here.

https://directaccess.richardhicks.com/2026/03/16/directaccess-iphttps-and-lets-encrypt-6-day-certificates/

Summary

If you are automating certificate enrollment and renewal, it shouldn’t matter if the certificate is valid for 6 days or 60 days. In fact, shorter lifetimes can significantly improve your security posture by minimizing risk and enforcing operational discipline around certificate management. Organizations that invest in automation today will be well-positioned to adopt even shorter certificate lifetimes in the future, while those relying on manual processes will find it increasingly difficult to keep up.

Questions?

Do you have questions about certificate lifecycle automation in your environment? I’m happy to help you validate your approach and address any challenges you’re encountering. Fill out the form below, and I’ll provide you with more information.

Additional Information

Let’s Encrypt Issues First Six-Day Certificate

DirectAccess IP-HTTPS and Let’s Encrypt 6-Day TLS Certificates

The Case for Short-Lived Certificates in the Enterprise

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