Welcome back to Guardians of the Directory! In this episode, Craig Birch is joined once again by Zero Trust expert Jerry Chapman for a deep dive into the Zero Trust Blueprint—a practical model to help organizations shift from theory to execution. Jerry shares insights from his work as Co-Chair of the CISA Zero Trust Working Group and provides a clear framework covering assessment, strategy, roadmap development, and execution phases.

Together, they explore:

• The critical role of business assets and protect surfaces

• Common pitfalls organizations face as they mature their Zero Trust implementations

• How Zero Trust applies equally to human and non-human identities (including AI!)

• The value of visibility, automation, and governance in maintaining Zero Trust momentum

If you're looking for a realistic, actionable guide to embedding Zero Trust in your enterprise—and especially within Active Directory environments—this episode is your blueprint.

Resources Mentioned:

• CISA Zero Trust Maturity Model

• CISA Zero Trust Working Group

• Microsoft Entra PIM

• Next-gen IGA and Certificate Lifecycle Management

Guest Bio:
Jerry Chapman is a cybersecurity veteran with over 25 years of experience in identity and Zero Trust. He serves as a Co-Chair for the CISA Zero Trust Working Group and is a recognized thought leader in strategy-driven security.

In this episode of Directory Insights in 10 Minutes, Craig Birch breaks down the often-misunderstood AdminSDHolder object in Active Directory and why it's a high-value target for attackers. Learn how the SDProp process uses it to secure privileged groups—and how misconfigurations or legacy permissions can open the door to persistent access.🔍 What you’ll learn:What AdminSDHolder and SDProp really doWhy this object matters for securing protected groupsHow attackers abuse it for persistenceHow to identify dangerous ACLs and misconfigurationsPowerShell tips to simplify your audit🛠️ PowerShell script to audit AdminSDHolder will be posted in the video description/comments.💡 If AdminSDHolder is compromised, your admin model is too.Subscribe for more quick-hit insights on Active Directory and Entra ID security.Powershell:Import-Module ActiveDirectory# DCSync-related GUIDs$dcsyncGUIDs = @( [Guid]"1131f6aa-9c07-11d1-f79f-00c04fc2dcd2", [Guid]"1131f6ad-9c07-11d1-f79f-00c04fc2dcd2", [Guid]"89e95b76-444d-4c62-991a-0facbeda640c")# Noisy identities to ignore$noisyAccounts = @( "NT AUTHORITY\SELF", "NT AUTHORITY\SYSTEM", "NT AUTHORITY\Authenticated Users", "NT AUTHORITY\INTERACTIVE", "BUILTIN\Pre-Windows 2000 Compatible Access", "Everyone")# AdminSDHolder ACL retrieval$domainNC = (Get-ADDomain).DistinguishedName$adminSDHolderDN = "CN=AdminSDHolder,CN=System,$domainNC"$adminSDHolder = Get-ADObject -Identity $adminSDHolderDN -Properties nTSecurityDescriptor$acl = $adminSDHolder.nTSecurityDescriptor# Admin group membership mappingfunction Get-AdminGroupMembers { param([string[]]$groupNames) $members = @() foreach ($name in $groupNames) { $group = Get-ADGroup -Identity $name $members += Get-ADGroupMember -Identity $group.DistinguishedName -Recursive | ForEach-Object { $_.SamAccountName } } return $members | Sort-Object -Unique}$adminGroups = @("Domain Admins", "Enterprise Admins", "Administrators")$adminMembers = Get-AdminGroupMembers -groupNames $adminGroups# Filter risky, non-default ACEs$dangerousACEs = $acl.Access | Where-Object { $_.AccessControlType -eq "Allow" -and -not ($noisyAccounts -contains $_.IdentityReference.Value) -and ( ($_.ActiveDirectoryRights -band "GenericAll") -or ($_.ActiveDirectoryRights -band "GenericWrite") -or ($_.ActiveDirectoryRights -band "WriteDacl") -or ($_.ActiveDirectoryRights -band "WriteOwner") -or ($_.ActiveDirectoryRights -band "CreateChild") -or ($_.ActiveDirectoryRights -band "Delete") -or ($_.ActiveDirectoryRights -band "DeleteTree") -or ($_.ActiveDirectoryRights -band "ExtendedRight") )}# Output$dangerousACEs | Select-Object ` IdentityReference, ActiveDirectoryRights, InheritanceType, ObjectType, @{Name="ACEType"; Expression={ if ($_.ActiveDirectoryRights -band "GenericAll") { "GenericAll" } elseif ($_.ActiveDirectoryRights -band "GenericWrite") { "GenericWrite" } elseif ($_.ActiveDirectoryRights -band "WriteDacl") { "WriteDacl" } elseif ($_.ActiveDirectoryRights -band "WriteOwner") { "WriteOwner" } elseif ($_.ActiveDirectoryRights -band "CreateChild") { "CreateChild" } elseif ($_.ActiveDirectoryRights -band "Delete") { "Delete" } elseif ($_.ActiveDirectoryRights -band "DeleteTree") { "DeleteTree" } elseif ($_.ActiveDirectoryRights -band "ExtendedRight") { if ($dcsyncGUIDs -contains $_.ObjectType) { "DCSync" } else { "ExtendedRight" } } else { "Other" } }}, @{Name="IsAdminGroupMember"; Expression={ $sam = $_.IdentityReference.Value.Split("\")[-1] $adminMembers -contains $sam }} | Format-Table -AutoSize

🔍 Admin Accounts with SPNs — Hidden Risk Behind Kerberoasting | Directory Insights in 10 MinutesIn this episode, Craig Birch breaks down a major Active Directory security blind spot: Kerberoasting via privileged accounts with SPNs (Service Principal Names).You'll learn how attackers exploit these accounts — and how to find, assess, and fix the risk without breaking your apps.Straightforward, no fluff — just practical identity security guidance.🛠️ What You’ll Learn🔐 What SPNs are — and why they matter⚠️ How attackers use them in Kerberoasting attacks🖥️ Why ADUC isn’t enough for visibility💻 PowerShell + LDAP filters for fast discovery🧠 SDProp and how it flags privileged accounts🤝 Why app owner collaboration is critical🔁 Safer alternatives: gMSAs, strong passwords, and role reviews❌ Why auto-remediation can break things💡 PowerShell SpotlightpowershellCopyEditGet-ADUser -LDAPFilter "(&(admincount=1)(servicePrincipalName=*))" -Properties servicePrincipalName | Select-Object Name, servicePrincipalNameUse this to find privileged accounts with SPNs — the ones most at risk of Kerberoasting.✅ Quick TakeawaysScript it — don’t rely on ADUCNever auto-remove SPNs without impact analysisTalk to app owners before changesHarden service accounts or switch to gMSAsMonitor SDProp-marked accounts to shrink attack surface💬 Found this helpful? Like, share, or comment! Got a topic you want us to cover in 10 minutes or less? Drop it below — we’re listening.

In this episode of Directory Insights in 10 Minutes, Craig Birch breaks down one of the most overlooked Active Directory misconfigurations: the "Do not require Kerberos pre-authentication" setting.🔍 Why it matters:Enables AS-REP Roasting attacks using tools like Hashcat or John the RipperAllows silent user enumeration without authentication failuresCan go undetected by SIEMs and security logs🛠️ What you'll learn:How this setting weakens AD securityHow attackers abuse it for initial access and password crackingHow to detect and remediate affected accounts using PowerShell🧠 Practical, fast, and built for real-world AD admins—no fluff.▶️ Chapters: 00:00 - Intro00:45 - Why “Do Not Require Pre-Auth” Is Dangerous02:30 - AS-REP Roasting Explained03:20 - Finding Vulnerable Accounts (GUI + PowerShell)05:40 - Remediation Script Walkthrough08:20 - Final Recommendations📥 PowerShell Script:# Import the Active Directory moduleImport-Module ActiveDirectory# Find user accounts that do not require Kerberos preauthentication$users = Get-ADUser -Filter {DoesNotRequirePreAuth -eq $true} -Properties DoesNotRequirePreAuth# Display the accounts that do not require Kerberos preauthentication$users | Select-Object Name, SamAccountName, UserPrincipalName# Pause for confirmation before remediationRead-Host -Prompt "Press Enter to remediate these accounts"# Remediate all accounts by setting DoesNotRequirePreAuth to $falseforeach ($user in $users) { Set-ADAccountControl -Identity $user -DoesNotRequirePreAuth $false}

Welcome to another episode of Directory Insights in 10 Minutes, powered by Guardians of the Directory. In this quick-hitting session, host Craig Birch walks through the process of identifying and remediating accounts in Active Directory that still rely on outdated Kerberos DES encryption.

🔐 DES is insecure and easily exploited by attackers. Craig shows you how to detect and update these accounts using both GUI and PowerShell—so you can act fast to protect your environment.

👉 If you find this helpful, give us a like, drop a comment, and suggest a topic for a future episode!

• Why DES-only encryption is dangerous in modern AD environments

• How to detect DES accounts using PowerShell

• Remediation using Set-ADUserAccountControl

• Upgrading users to use stronger AES encryption

• Fast, actionable tips to secure your Active Directory

🛠️ Key Takeaways:

Why DES-only encryption is dangerous in modern AD environments

• How to detect DES accounts using PowerShell

• Remediation using Set-ADUserAccountControl

• Upgrading users to use stronger AES encryption

• Fast, actionable tips to secure your Active Directory

Summary:

In this episode of Directory Insights in 10 Minutes, we dive into a critical yet often overlooked Active Directory misconfiguration—Allowing Password Storage with Reversible Encryption.

This setting can override password policies, leaving user credentials exposed to plaintext extraction through common attacker tools like Mimikatz and DCSync.

🚨 Key Takeaways:
✅ How this misconfiguration bypasses domain password policies
✅ How attackers can extract plaintext passwords using AD credential dumping tools
✅ How to find vulnerable accounts using PowerShell
✅ How to remediate and secure your AD environment

Episode Overview

In this episode of Directory Insights in 10 Minutes, we’re exposing a dangerous yet overlooked Active Directory misconfiguration—PasswordNotRequired.

Most AD admins assume password policies protect all accounts. They don’t. This attribute allows accounts to override domain password policies, making them vulnerable to blank passwords and easy takeovers.

What is the "Password Not Required" Attribute?

• A hidden AD attribute that allows accounts to exist without a password.
• Bypasses domain password policies, including length, complexity, and history requirements.
• Affects privileged accounts, service accounts, trust accounts, and regular users.

Why is This a Risk?

• Attackers (or insiders) can reset the password to blank and gain instant access.
• Any account with this misconfiguration is an easy target for privilege escalation.
• Most AD admins don’t even know this setting exists—but attackers do.

Directory Insights in 10 Minutes – Episode 1
🛡️ AD’s Biggest Misconfiguration – Fix It Now!

Description:
Welcome to the first episode of Directory Insights in 10 Minutes, brought to you by Guardians of the Directory. This series is all about cutting through the noise—no fluff, no filler—just real-world, practical security insights for Active Directory and Entra ID admins.

In this episode, we’re exposing the #1 misconfigured setting in Active Directory—one that attackers love and admins often overlook. Even today, in 2025, this security gap exists by default in every new AD deployment.

What You’ll Learn:
✅ Why the built-in Administrator account (RID 500) is vulnerable out of the box
✅ How attackers abuse Kerberos delegation to impersonate admin accounts
✅ Why Microsoft’s security guidance is buried in a 2,000-page document
✅ The one checkbox that removes this attack path instantly
✅ Why Protected Users group doesn’t fully mitigate this risk

🛠️ Quick Fix:
1️⃣ Go to RID 500 account properties
2️⃣ Under the Account tab, check "Account is sensitive and cannot be delegated."
3️⃣ Apply this setting to all administrative accounts
4️⃣ Implement this as part of your ongoing security process

Summary

In this episode of Guardians of the Directory, host Craig Birch interviews Kevin Kampman, a veteran in directory services, discussing the evolution of Active Directory, its challenges, and the future of directory management. They explore the historical context of directory services, the impact of cloud technology, and the importance of naming conventions in directory management. Kevin shares valuable lessons for today's directory administrators and offers insights into the future landscape of directory services, emphasizing the need for adaptability and understanding of complex systems.

Key Takeaways

Active Directory has evolved significantly since its inception in 2000.

The integration of cloud services has introduced new challenges for directory management.

Naming conventions are critical for effective directory administration.

Understanding the history of directory services is essential for future success.

The future of directory services will involve more complexity and interconnectivity.

AI will play a significant role in managing directory services in the future.

Organizations must adapt to changing technology landscapes to remain effective.

Collaboration between different teams is crucial for successful directory management.

Risk assessment is important in directory administration.

Continuous learning and mentorship are vital for new directory administrators.

In this episode of Guardians of the Directory, Craig Birch and Jerry Chapman delve into the concept of Zero Trust in cybersecurity. They discuss its principles, models, and the importance of identity-led security. The conversation highlights the five pillars of Zero Trust, the challenges organizations face with data management, and the complexities of securing applications in a cloud environment. They emphasize the need for continuous governance, automation, and practical steps organizations can take to implement Zero Trust effectively. The episode concludes with advice on starting small and making incremental improvements in security practices.