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 Ask Me Anything (AMA) April 2026

We’re already through most of Q1 2026, so I’ve put another AMA on the calendar so we can all connect again. Be sure to join me on Tuesday, April 7, at 10:00 AM PDT (UTC -7) for the next edition of the Always On VPN AMA (Ask Me Anything!) session.

Do you have questions about Always On VPN? Are you having a specific issue you can’t figure out? Would you like more information about configuration options? Here’s your chance to get your questions answered! Register now and join the session to ask me anything (AMA!) about Microsoft Windows Always On VPN and related technologies.

The AMA will be an open forum session where we can all talk shop about Always On VPN and related technologies. It’s a great chance to learn new things and share experiences with your peers. We’ll discuss known issues and limitations, best practices, and more. I’m also planning to have some special guests, so be sure to join us!

Everyone is welcome. Don’t miss out on this excellent opportunity to connect and learn. Register now!

Can’t make the session? Register anyway, and I’ll send you the link to the recording as soon as it is available!

Always On VPN Ask Me Anything (AMA) November 2025

It’s been a while since we’ve held our last AMA, so I’ve added an event to the calendar so we can all connect once more before the end of the year. With that, the next Always On VPN AMA session is scheduled for Tuesday, November 18, 2025, at 10:00 AM PDT (UTC-8).

Do you have questions about Always On VPN? Are you having a specific issue you can’t figure out? Would you like more information about configuration options? Here’s your chance to get your questions answered! Register now and join the session to ask me anything (AMA!) about Microsoft Windows Always On VPN and related technologies.

The AMA will be an open forum session where we can all talk shop about Always On VPN and related technologies. It’s a great chance to learn new things and share experiences with your peers. We’ll discuss known issues and limitations, best practices, and more. I’m also planning to have some special guests, so be sure to join us!

Everyone is welcome. Don’t miss out on this excellent opportunity to connect and learn. Register now!

Can’t make the session? Register anyway, and I’ll send you the link to the recording as soon as it is available!