Techmentor Event Microsoft HQ 2026

I’m pleased to announce I’ll be attending the Techmentor Event at Microsoft Headquarters in Redmond, WA, August 3-7, 2026. Register now and save $500.00 with the discount code HICKS.

Sessions

I’ll be delivering three sessions at this year’s event.

Join Me

The event is shaping up to be one of the best, with industry experts from around the world presenting on many important topics. Be sure to join me! Don’t miss out on this fantastic opportunity to learn from the best in the industry. Register today. Hope to see you there!

What’s New in Always On VPN DPC v5.4.0

A new edition of the popular Always On VPN Dynamic Profile Configurator (DPC) is now available. Version 5.4.0, released on May 5, 2026, includes some new features, reliability improvements, and additional miscellaneous fixes.

What’s New in DPC v5.4.0

The following new features and improvements are included in the latest release of DPC.

Signed Binaries

Beginning with release v5.4.0, all binaries, including the installer, are digitally signed. This streamlines the installation process and allows DPC to better integrate with application controls.

EAP-TLS

By popular demand, EAP-TLS support has been added as an authentication option in DPC. Historically, DPC strictly adhered to security best practices and only allowed Protected EAP (PEAP). However, many administrators required EAP-TLS to better integrate with non-Microsoft VPN services.

Additional Enhancements

Other changes include better profile change comparison and a new logo. In addition, the DPC ADMX files are now publicly accessible on ADMScope.

Summary

Administrators running earlier versions of DPC are encouraged to upgrade to v5.4.0 as soon as possible.

Additional Information

Always On VPN DPC v5.4.0 on GitHub

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