WEBINAR: Preparing for 100-Day Certificates with CertKit

Join me and the CertKit team on Tuesday, October 6, 2026, at 9:00 AM PDT for a free, live webinar about the upcoming reduction in public TLS certificate lifetimes. Beginning March 15, 2027, the maximum validity period for public TLS certificates will be reduced to 100 days. This change will make manual certificate management increasingly difficult for many organizations.

Automation

Shorter certificate lifetimes require organizations to identify, enroll, deploy, and renew certificates more frequently. Automation can help reduce the administrative effort and the risk of service interruptions caused by expired certificates. This is especially important for public-facing Microsoft workloads such as Internet Information Services (IIS), Remote Desktop Services (RDS), Always On VPN, DirectAccess, and other services that use public TLS certificates.

Visibility

Effective certificate management begins with knowing which certificates exist, where they are installed, and when they expire. Without this visibility, organizations may overlook certificates until they are close to expiration or have already expired.

Internal Certificates

Certificates issued by a private certification authority (CA) aren’t subject to the lifetime restrictions imposed on public TLS certificates. However, they still require inventory, monitoring, and renewal. A consistent approach to managing public and private certificates can help reduce operational overhead.

How CertKit Helps

CertKit is a cloud-based service for managing public and private TLS certificates. During the webinar, we’ll demonstrate how CertKit provides visibility into certificate inventories and expiration dates while automating common lifecycle tasks such as enrollment, deployment, and renewal. We’ll also review recent additions to the service.

Register Now

The webinar takes place on Tuesday, October 6, at 9:00 AM PDT. Registration is required. Everyone who registers will be notified when the session recording is available.

Live! 360 Event Orlando, Florida 2026

I’m excited to announce that I’ll be attending the upcoming Live! 360 Event, November 15-20, 2026, at Royal Pacific Resort at Universal Orlando, Florida. I’ll be in attendance all week and will be delivering a few talks at the event this year.

Sessions

I’ll be presenting two sessions at this year’s event. They are:

Join Me!

If you are planning to attend the event, please join my sessions! I will be at the conference center all week, so don’t hesitate to reach out and contact me while you are there. I’m looking forward to seeing everyone soon!

Always On VPN Dynamic Profile Configurator (DPC) Webinar

Managing Microsoft Always On VPN deployments doesn’t have to be complicated. Always On VPN Dynamic Profile Configurator (DPC) is a free, open-source solution that simplifies deploying and managing Always On VPN client configuration settings while extending the capabilities of native deployment methods such as Microsoft Intune VPN profiles, custom XML, and PowerShell scripts.

Whether you’re deploying Always On VPN for the first time or looking to streamline an existing implementation, DPC provides powerful features that make advanced VPN configuration easier to deploy, manage, and maintain.

Join Our Live Webinar

Join me on Tuesday, August 18, at 1:00 PM EDT for a live webinar featuring Leo D’Arcy, creator and lead developer of Always On VPN DPC. During this live session, we’ll demonstrate many of DPC’s latest capabilities and show how they can simplify even the most complex Always On VPN deployments. Topics include:

  • Configuring flexible VPN deployment strategies
  • Optimizing interface and route metrics
  • Dynamically excluding Microsoft 365 and custom domains from the VPN tunnel
  • Configuring IKE mobility settings for improved roaming
  • Defining and managing IPv6 routes
  • Deploying DPC using Active Directory and Microsoft Intune
  • Exploring additional advanced features and deployment scenarios

Throughout the webinar, we’ll share practical guidance, configuration tips, and real-world examples to help you get the most from Always On VPN DPC.

Register Today

Registration is free, but you must register in advance to attend. If you can’t attend the live session, register anyway, and you’ll receive access to the on-demand recording after the event.

We’ll also reserve time for a live Q&A at the end of the presentation, giving you the opportunity to ask questions directly to the developers and experts behind DPC.

We look forward to seeing you there!

Additional Information

Always On VPN Dynamic Profile Configurator (DPC)

Always On VPN DPC Advanced Features

Always On VPN DPC with Microsoft Intune

Migrating from Always On VPN DPC Commercial to Open Source

Always On VPN DPC Commercial Support Now Available

Always On VPN DPC Discord Channel

Windows Server Inside Out Book Updated for Windows Server 2025

Orin Thomas, a Principal Hybrid Cloud Advocate at Microsoft, is a prolific technical author who has written more than 45 books for Microsoft Press since the early 2000’s. His latest work is an update to the popular Windows Server Inside Out series, now covering the latest release of the operating system, Windows Server 2025. With Windows Server 2016 rapidly approaching end of support in January 2027, now is the time to start migrating workloads to Windows Server 2025. No doubt this book will make deploying and managing this new operating system much easier.

Order Now!

You will find Windows Server 2025 wherever you purchase your technical books, including Amazon.

Windows Server 2025 Inside Out – Paperback

Windows Server 2025 Inside Out – Kindle Edition

Mastering Certificates with Microsoft Intune September 2026

I’m excited to announce that I will be delivering another edition of the Mastering Certificates with Microsoft Intune course, hosted by ViaMonstra Online Academy. This is a three-day live online training course that takes place September 1-3, 2026. This course dives deep into issuing and managing certificates using Microsoft Intune, covering both on-premises and cloud-based solutions.

Course Overview

This interactive training equips IT professionals with the skills to provision and manage enterprise PKI certificates using Microsoft Intune. It explores Active Directory Certificate Services (AD CS), Microsoft Cloud PKI for Intune, and non-Microsoft solutions, with live demonstrations featuring real-world scenarios.

Key Learning Objectives

Those taking the online training course will learn the following.

  • Certificate Basics: Understand certificate roles and enterprise use cases.
  • Deployment Options: Master Intune certificate deployment (Intune policies, revocation, security) and Microsoft Cloud PKI (licensing, benefits, limitations, BYOCA).
  • Intune Deployment: Learn PKCS and SCEP deployment, security best practices, and troubleshooting.
  • High Availability: Explore strategies for reliable certificate management.

Course Highlights

Here are some key highlights for attendees of the training.

  • Expert-Led: Learn from a veteran IT professional, a Microsoft MVP, with deep PKI and Intune expertise.
  • Interactive Demonstrations: The course includes numerous practical exercises in real-world scenarios.
  • Resources: Access to security best practices and sample scripts for automated configuration.
  • Community: Join a private Facebook group for peer collaboration.
  • Live Q&A: Engage directly with the instructor for a clearer understanding.

Who Should Attend?

This training event is ideal for IT administrators, security professionals, and systems engineers working with Intune, AD CS, or Microsoft Cloud PKI for Intune.

Prerequisites

Those attending the online training course should be familiar with the following.

  • Basic networking knowledge (TCP/IP, DNS).
  • Familiarity with Active Directory, Windows OS, and Intune.
  • Access to an AD CS setup and an Azure subscription with Intune Suite licenses.

Why It Matters

Certificates are vital for secure authentication and communication. This course bridges theory and practice, equipping you to deploy and manage digital certificates effectively in cloud-native environments.

Details

Here is some additional information about the training event.

  • When: September 1-3, 2026 (sessions begin at 9:00 AM CDT).
  • Where: Live online via ViaMonstra Online Academy.
  • Cost: $2,395.00 (Sold separately – not included in All-Access Pass).

Why ViaMonstra?

ViaMonstra delivers top-tier IT training from Microsoft MVPs, focusing on practical, up-to-date skills and fostering a collaborative community.

Take the Next Step

Ready to master certificate management with Microsoft Intune? Register at ViaMonstra Online Academy for the August 2025 Mastering Certificates with Microsoft Intune training course today!

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.

Missed the event? Watch the on-demand replay here.

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.

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!

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.

Did you miss the webinar? You can view it on demand here!

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!

Recording

If you missed the live event, you can view the on demand recording here!

Midwest Management Summit (MMSMOA) 2026

I’m excited to be presenting two sessions at the upcoming Midwest Management Summit at Mall of America (MMSMOA), taking place May 3-7, 2026, at the Radisson Blu in Bloomington, MN. This is the premier systems management event in the U.S., offering unrivaled access to Microsoft and industry professionals from around the world.

Cloud PKI for Intune

My first session, Zero to Certificates in 5 Minutes with Cloud PKI for Microsoft Intune, covers how to quickly configure and deploy certificates using Cloud PKI for Microsoft Intune. This session is ideal for anyone looking to streamline certificate management without the traditional heavy infrastructure burden.

Entra Private Access

My second session, Moving to Zero Trust: Entra Private Access for Always On VPN Administrators, explores the transition from traditional Always On VPN to Microsoft’s Entra Private Access, highlighting practical steps, architectural differences, and the benefits of maintaining secure access in a modern Zero Trust environment. I will also share important migration tips, tricks, and best practices.

Let’s Connect!

Looking forward to diving into these topics with everyone there. I hope to see some familiar faces and meet new ones, too! If you are attending the event, be sure to say hello!

Additional Information

Midwest Management Summit at Mall of America (MMSMOA)

Cloud PKI for Microsoft Intune on RunAs Radio

Microsoft Entra Private Access on RunAs Radio

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!