Category: Cybersecurity (Page 1 of 6)

Part 4: Using Certificate Enrollment Services in Practice

August 8, 2026 / Michael Waterman / 0 Comments

In the previous parts of this series, I’ve looked at the architecture behind Microsoft Certificate Enrollment Services and built both the Certificate Enrollment Policy Web Service (CEP) and Certificate Enrollment Web Service (CES). At this point, all the server-side components are in place. But having a working CEP and CES infrastructure is only half the story. Ultimately, a client needs to know where to retrieve certificate enrollment policy, determine which certificate templates it is allowed to use, discover the appropriate enrollment service, and finally submit a certificate request. That’s what I will show you in this part.

I will configure Windows clients to use our CEP service in two different ways. First, I will use Group Policy, which is the obvious choice for centrally managed domain-joined systems. After that, I will configure the enrollment policy locally, which is useful for individual systems and becomes particularly interesting when working with devices that cannot rely on Active Directory Group Policy. I will then follow the complete process from policy discovery to certificate enrollment and look at what Windows is actually doing behind the scenes.

Part 3: Installing the Certificate Enrollment Web Service (CES)

August 3, 2026 / Michael Waterman / 0 Comments

In the previous article, we deployed the Certificate Enrollment Policy Web Service (CEP) and configured support for Kerberos, Username/Password, and Client Certificate authentication. Clients can now successfully retrieve certificate enrollment policies over HTTPS using the XCEP protocol. However, while the policy infrastructure is now in place, clients still have no way to request certificates.

In this article, I’ll complete the Microsoft Certificate Enrollment Services architecture by deploying the Certificate Enrollment Web Service (CES). I’ll prepare Active Directory, configure a dedicated Group Managed Service Account (gMSA), install IIS, deploy the CES role, configure the supported authentication methods, and validate the deployment using PowerShell. By the end of this article, you’ll have a fully operational Certificate Enrollment Web Service capable of securely processing certificate requests over HTTPS using the WSTEP protocol.

Part 2: Installing the Certificate Enrollment Policy Web Service (CEP)

August 3, 2026 / Michael Waterman / 0 Comments

In the first article of this series, I explored the architecture behind Microsoft Certificate Enrollment Services (CEP & CES) and discussed why Microsoft introduced these web services.I looked at the differences between traditional Active Directory Certificate Services enrollment and the HTTPS-based enrollment model, explained the XCEP and WSTEP protocols, and followed the complete certificate enrollment process from start to finish. Now it’s time to move from theory to implementation.

In this article, I’ll build a complete Certificate Enrollment Policy Web Service (CEP) from scratch using PowerShell. Rather than simply installing the Windows role, I’ll also prepare Active Directory, create the required security groups, configure a Group Managed Service Account (gMSA), install IIS, configure the supported authentication methods, and validate that the deployment is functioning correctly. By the end of this article, you’ll have a fully operational Certificate Enrollment Policy Web Service capable of serving enrollment policies over HTTPS using Kerberos, Username/Password, or Client Certificate authentication.

Part 1: Understanding Microsoft Certificate Enrollment Services (CEP & CES)

August 2, 2026 / Michael Waterman / 2 Comments

If you’ve ever worked with Microsoft Active Directory Certificate Services (AD CS), you’ve probably come across the Certificate Enrollment Policy Web Service (CEP) and the Certificate Enrollment Web Service (CES). While Microsoft provides documentation on both services, I often notice that the focus is on how to install them rather than why they exist and how they fit into the bigger picture.

When I started diving into CEP and CES myself, I quickly discovered that understanding the architecture is far more important than simply clicking through an installation wizard. Why are there two separate web services? What problem were they designed to solve? What are XCEP and WSTEP? And when should you actually consider deploying CEP and CES instead of relying on traditional certificate enrollment?

What’s a Certificate Anyway

July 16, 2026 / Michael Waterman / 0 Comments

One of the questions I get asked most often during assignments or workshops isn’t really about Certificate Revocation Lists (CRLs), OCSP, certificate templates or PKI in general. It’s much simpler than that.

“What’s a certificate anyway?”

Well actually, I sometimes start with the question, “So, can anyone explain to me what a certificate is or what it represents?”. You would think, it seems like an easy question to answer. Some people will tell you it’s your public key. Others will say it’s your digital identity. While both answers contain some truth, rarely the complete story is told. A digital certificate is much more than a single piece of information. It contains an identity, a public key, validity information, a collection of extensions, and much more. More importantly, all of that information is cryptographically protected by a trusted Certificate Authority (CA).

In other words, a certificate is a digitally signed document that binds an identity to a public key, with a couple of extensions. That digital signature allows anyone who trusts the issuing CA to verify that the certificate has not been modified and that the binding between the identity and the public key is authentic. But what exactly is inside a certificate? What does a Certificate Authority actually sign? And why does changing just a single character invalidate the entire certificate?

Let’s take a look under the hood of an X.509 certificate.

Taking the FUD out of PQC

July 2, 2026 / Michael Waterman / 0 Comments

“But Mike… there is no FUD in Post-Quantum Cryptography.”

I’m glad you brought that up, because that’s exactly what this post is about.

When people hear the term Post-Quantum Cryptography (PQC), the conversation often goes in one of two directions. Some claim that quantum computers are still decades away and that there’s nothing to worry about. Others make it sound as if RSA will stop working sometime next Tuesday, neither view tells the whole story. The reality is far more interesting, and far more nuanced than many have you believe, Post-Quantum Cryptography isn’t about fear, uncertainty, or doubt. It’s about understanding the actual risks, separating scientific facts from headlines, and making informed architectural decisions based on evidence rather than speculation.

So, let’s take the FUD out of the discussion. In this blog, we’ll look at what current research actually tells us about quantum computers, why symmetric encryption such as AES is in a very different position than RSA and ECC, who is realistically capable of building a cryptographically relevant quantum computer, and why organizations should begin preparing today, even though the first machine capable of breaking modern public key cryptography is unlikely to appear in your local datacenter anytime soon. Because the real challenge isn’t that quantum computers are coming. The real challenge is making sure your organization is ready when they do.

How Merkle Tree Certificates Work

June 27, 2026 / Michael Waterman / 0 Comments

For more than 35 years, X.509 certificates have formed the foundation of digital trust on the Internet and in many organizations alike. From HTTPS and VPNs to enterprise authentication and code signing, the basic architecture has remained unchanged. As we enter the post-quantum era, however, it may not be the cryptographic algorithms that need the biggest overhaul, but the certificate model itself.

Imagine a Certificate Authority such as Let’s Encrypt issuing hundreds of millions of post-quantum certificates. Every one of those certificates now carries a digital signature that is significantly larger than today’s RSA or ECC signatures. Suddenly, TLS handshakes become larger, certificate chains consume more bandwidth, Certificate Transparency logs grow faster, and browsers have considerably more data to process. Everything just slows down.

The challenge is no longer whether post-quantum cryptography works. The challenge is whether the X.509 certificate architecture can continue to scale in a post-quantum world. This is exactly the problem that Merkle Tree Certificates (MTC) are designed to solve.

AD CS Performance Toolkit

June 15, 2026 / Michael Waterman / 0 Comments

During many of the Active Directory Certificate Services (AD CS) projects I work on, the discussion always turns to performance. “So Mike, how to we need to scale the machines?” Is the virtual hardware powerful enough? Do we have sufficient memory? How many CPU cores should the Certification Authority have? Is our Hardware Security Module (HSM) fast enough? Will disk I/O become a bottleneck? And perhaps the simplest question of all:

How fast is Active Directory Certificate Services actually?

Another challenge I regularly encounter is the need for a realistic Certification Authority database. Whether demonstrating reporting capabilities, validating certificate templates, testing custom PowerShell scripts, or creating a representative lab environment, an empty CA database simply does not reflect production. After searching for a suitable solution, I realized that nothing really existed that combined realistic certificate generation with meaningful performance benchmarking. Existing tools either focused on enrollment or stress testing, but none provided detailed insight into where certificate issuance time was actually spent….so I built one.

The AD CS Benchmark & Performance Analysis Toolkit is a PowerShell-based utility that generates realistic PKCS#10 certificate requests, submits them through the native ICertRequest2 COM interface, optionally creates matching Active Directory objects, and records detailed timing information for every stage of the enrollment process.

Building a Highly Available CRL and AIA Distribution Platform for AD CS

June 4, 2026 / Michael Waterman / 0 Comments

Last time I wrote about the why a Certificate Revocation List (CRL) should be available for the majority of services that make use of certificates. One of those prime examples is the use of smartcards. When revocation can’t be checked, you simply can not logon. Most Microsoft PKI deployments start with a single web server hosting the CRL Distribution Point (CDP) and Authority Information Access (AIA) locations. While this works well for smaller environments or labs, it introduces a single point of failure. If the web server becomes unavailable, certificate revocation checking may fail and certificate validation can be disrupted across the environment.

The Reality Behind PKI Revocation Checking

May 25, 2026 / Michael Waterman / 4 Comments

Last week I attended an interesting PKI training from CQURE. I never really had any formal PKI training before, mostly because I’ve spent years learning it the way many infrastructure engineers do, by breaking things in labs, fixing production issues, and occasionally questioning my life choices while staring at certutil output at 2 AM.

Still, I thought it would be fun to join. Most of the material was already familiar, but I met interesting people, had some good discussions, and definitely learned a few new things along the way. If you want to get into Microsoft PKI, I can genuinely recommend the training. PKI is one of those subjects that somehow manages to be both incredibly boring and extremely fascinating at the same time.

One of the topics we discussed was revocation checking. In the Microsoft world, this usually means Certificate Revocation Lists (CRLs) or the Online Certificate Status Protocol (OCSP). What many people misunderstand, however, is that revocation checking is not some universally enforced security mechanism. Whether revocation is actually checked often depends entirely on the application, service, operating system, or even the exact API being used underneath.