Entra.Chat

What does it take to migrate 40,000 devices to a cloud-native environment in a massive, complex enterprise? For most IT leaders, the prospect of moving away from 20 years of legacy infrastructure is enough to cause a sleepless night.
In our latest episode of Entra Chat, we sat down with enterprise veterans Michael Brunker and Prem Kothandapani to deconstruct their recent, massive rollout. They successfully converted nearly 40,000 devices from on-premises Active Directory to Entra Joined in just nine to ten months—all with a lean team of 10–15 people.
Here are the high-stakes lessons they learned from the trenches of modern management.
The “Nuclear Option”: Cleaning Up 20 Years of GPO Debt
One of the most controversial decisions the team made was what they called the “nuclear option” regarding Group Policy Objects (GPOs). Instead of porting over decades of legacy policies that no one fully understood, they chose to start from scratch.
By building a new security baseline from the ground up in Intune, they ensured the new environment was clean, modern, and free from the “stale” configurations that often plague legacy estates.
Killing the “VPN Tax”
For the end user, the primary driver for this migration was a radically improved experience. In a cloud-native world, the dependency on legacy VPN technology disappears.
* Work from Anywhere: Users can sign on and get access without the friction of starting a VPN or worrying about office cabling.
* Security at the Edge: Moving to Entra ID shrinks the attack surface by removing devices as a direct entry point to your core on-prem Active Directory.
Sponsored by:
If you’re a systems administrator, you already know – patching is painful. It’s time-consuming, risky, and one small mistake can mean downtime. So, it gets postponed. Again. And again. What if patching was just… Easy?
Introducing Action1, a cloud-native patch management platform for Windows, macOS, Linux, and third-party apps. You’ll be up and running in five minutes. No infrastructure to maintain. No complexity.
And here’s the best part: you can use Action1 on your first 200 endpoints for free. Forever. No feature limits. No credit card. No hidden tricks. Seriously, It’s NOT a disguised free trial. Too good to be true? Too good and actually true! Check for yourself, go to: on.action1.com/entrachat
So, if you’re looking for an easy-to-use patching tool that would help you save weeks, if not months of your time, go to on.action1.com/entrachat and sign up for “Patching That Just Works”.
The “Gnarly” Problems: What Breaks First?
Success wasn’t just about the big picture; it was about mastering the “fundamental basic building blocks”. Michael and Prem highlighted several technical hurdles that can derail a migration if not handled early:
* The Proxy Trap: Many organizations fail to update their proxy server allow-lists with the specific Microsoft URLs required for cloud authentication.
* App Authentication: Moving from Kerberos-based device auth to OAuth and modern cloud flows requires rigorous testing across different “personas,” such as front line workers versus corporate office users.
The Secret to Scaling: Small Teams, Big Strategy
Perhaps the most surprising takeaway was that a project of this scale didn’t require an army. By focusing on a “small team” of highly skilled engineers and dedicated communications experts, they maintained momentum and avoided “stop-start” migration fatigue.
Want to hear the full technical breakdown, including how they handled zero-downtime requirements for front line workers?
Subscribe with your favorite podcast player or watch on YouTube 👇

About Michael Brunker
Michael Brunker has approaching 40 years in the IT industry and has operated as an enterprise architect across major organizations like BP, Woodside, and Telstra.
LinkedIn - https://www.linkedin.com/in/michaelbrunker/
About Prem Kothandapani
Prem Kothandapani is an EndPoint Architect with over 14 years of experience in endpoint computing and major migrations, having worked at NBN, Australian Unity, and Telstra.
LinkedIn - https://www.linkedin.com/in/premnath-kothandapani-41744153/
📗 Chapters
00:00 Cloud-Native Device Management
02:58 The True Cost of Legacy Infrastructure
07:47 Moving to Modern Management
11:13 The Blueprint for a 40,000 Device Migration
20:07 Handling Complex App Dependencies
28:07 Crafting a Seamless User Migration Experience
33:28 Automating with Graph API and Autopilot
43:09 Avoiding the Co-Management Trap
55:01 The New Starter Experience
57:24 Migration Velocity and Lessons Learned
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill


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March 2026 is shaping up to be one of the most important months for Microsoft Entra ID administrators in recent memory.
Microsoft is automatically enabling passkey profiles in Entra ID, and if you don’t configure them yourself, your tenant will be migrated with default settings.
In this episode of Entra Chat, I sat down with Microsoft Security MVPs Daniel Bradley and Ewelina Paskowska to break down what this really means for Microsoft 365 administrators.
But passkeys aren’t the only story this month.
1️⃣ Passkey Profiles Are Becoming the Default
Starting March 2026:
* Passkey profiles will be auto-enabled
* Tenants that haven’t configured profiles will be migrated
* Registration campaigns will shift from Authenticator-first to passkey-first
This is a major shift toward phishing-resistant authentication.
You’ll now be able to:
* Separate hardware-backed vs synced passkeys
* Apply granular group-based controls
* Enforce stronger authentication for privileged users
2️⃣ Source of Authority Conversion Is Finally GA
For years, admins used messy delete-and-restore hacks to convert synced users to cloud-only.
Now it’s officially supported.
You can convert individual users from on-premises authority to cloud-managed — without breaking hybrid entirely.
Why this matters:
* Easier M&A transitions
* Full access to Entra ID Governance features
* Cleaner lifecycle management
* Reduced dependency on legacy infrastructure
For hybrid environments moving toward cloud-first identity, this is huge.
Sponsored by:
If you are a systems administrator managing endpoints every day, you’ve probably postponed patching at least once — not because you forgot… But because you didn’t feel like gambling with uptime. Meanwhile, the backlog grows, vulnerabilities pile up, and patching stays stuck in manual mode.
Action1  fixes that.
Action1 is a cloud-native patch management platform for Windows, macOS, Linux, and third-party apps — all from one place, no VPN needed. Curious how easy it is to start? You can use it on your first 200 endpoints, for free, forever, with no functional limits. It’s not a disguised free trial. No credit card required, no hidden limits, no tricks.
All you have to do is visit on.action1.com/entrachat and get started today.
So, if you’re looking to automate patching at scale and get weeks— even months—of your time back, go to on.action1.com/entrachat and sign up for patching—that—just—works.
3️⃣ App Registration Deactivation (A Quietly Powerful Feature)
Microsoft added the ability to deactivate app registrations.
Instead of deleting an app (and losing configuration), you can now:
* Immediately stop token issuance
* Preserve metadata and permissions
* Investigate safely
* Re-enable without rebuilding
For incident response scenarios — especially in multi-tenant or MSP environments — this is a big step forward.
4️⃣ Conditional Access Behavior Changes
There’s also a change impacting tenants with Conditional Access policies targeting “All resources” but excluding certain apps.
Previously, certain minimal-scope apps could bypass enforcement under specific conditions.
That loophole is closing.
Admins should:
* Review message center notifications
* Audit legacy apps
* Validate MFA handling before rollout
As always with identity changes: being proactive is critical.
5️⃣ Sync Security Hardening (Hard Match Protection)
Microsoft is adding additional validation to protect against malicious hard matching scenarios in hybrid environments.
This reduces the risk of identity takeover via manipulated on-prem objects.
It’s automatic — but important to understand if you manage hybrid identity or MSP transitions.
Watch the full episode for the deep technical breakdown and real-world implications.
Subscribe with your favorite podcast player or watch on YouTube 👇

About Daniel Bradley
Daniel is a Senior Solution Architect for CDW and Microsoft MVP in Identity & Graph API. He is a avid writer who enjoys investigating new features and building practical tools to share with the community through his blog. He also is one of the moderators for the r/entra subreddit.
* Website: https://ourcloudnetwork.com
* LinkedIn: https://www.linkedin.com/in/danielbradley2
* X: https://x.com/DanielatOCN
About Ewelina Paczkowska
Ewelina is a Solution Architect at Theatscape and a Microsoft Security MVP. She is a content creator and speaker who enjoys breaking down complex solutions into clear, practical guidance. Ewelina is also an organiser of the Microsoft 365 Security & Compliance user group and the creator behind Welka’s World, where she shares insights and real-world knowledge around Microsoft security and compliance.
* Website: https://welkasworld.com
* LinkedIn: https://www.linkedin.com/in/ewelinapaczkowska
* X: https://x.com/WelkasWorld
🔗 Related Links
* MC1221452 - Microsoft Entra ID: Auto-enabling passkey profiles - https://mc.merill.net/message/MC1221452
* Ability to convert Source of Authority of synced on-prem AD users to cloud users is now available - https://learn.microsoft.com/en-us/entra/identity/hybrid/user-source-of-authority-overview
* Service Principal creation audit logs for alerting & monitoring - https://learn.microsoft.com/en-us/entra/identity/monitoring-health/understand-service-principal-creation-with-new-audit-log-properties
* Deactivate an app registration - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/deactivate-app-registration
* MC1223829 - Upcoming Conditional Access change: Improved enforcement for policies with resource exclusions - https://mc.merill.net/message/MC1223829
* Microsoft Entra Connect security hardening to prevent user account takeover - https://learn.microsoft.com/en-us/entra/fundamentals/whats-new#general-availability---microsoft-entra-connect-security-hardening-to-prevent-user-account-takeover
📗 Chapters
06:16 Converting Source of Authority to Cloud
15:37 Auto-Enabling Passkey Profiles
24:33 Deactivating App Registrations
31:56 Conditional Access for Excluded Apps
38:48 Sync Jacking Protection
41:45 Unified Tenant Configuration Management
46:31 Service Principal Creation Logs
Podcast Apps
🎙️ Entra.Chat → https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill


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Governance in Microsoft 365 has always been hard. Not because the tools didn’t exist, but because scale, complexity, and change made consistency almost impossible. As tenants grow, so do the challenges of configuration drift, manual admin changes, and inconsistent environments.
For years, admins have relied on scripts, tribal knowledge, and community-led solutions like Microsoft 365 Desired State Configuration (M365DSC) to manage this “policy sprawl”. While M365DSC was a groundbreaking open-source effort, it often faced a steep learning curve and lacked official Microsoft support.
Until now.
In this episode of Entra Chat, we sit down with Nik Charlebois, Principal Program Manager at Microsoft and the original visionary behind M365DSC. Nik now leads the charge for one of the most significant platform shifts in Microsoft 365 administration: Tenant Configuration Management (TCM).
Shadow IT and SaaS sprawl are outpacing IT teams
It can feel impossible to tackle these app governance challenges:📦 Entra ID isn’t secure by default💥 SaaS adoption & sprawl isn’t slowing down⌨️ Citizen Development keeps rising (hello, Copilot Studio!)🗑️ Vendors often don’t remove apps after uninstall🔃 Offboarding is inconsistent or doesn’t happen at all🥔 App governance is passed around like a hot potato
ENow AppGov Score shines a light on lurking risks, providing a free App Governance Benchmark Report for your Entra tenant. Reclaim control and protect against breach & disruptions. Free upgrade to Standard Tier for 7 days once you get your score.
What is Tenant Configuration Management?
TCM is Microsoft’s official “Config as Code” platform for M365. Built directly on top of the Microsoft Graph, it represents a new operating model for how tenants are governed.
Key features discussed in this episode include:
* Official Support: Moving beyond best-effort community maintenance to a fully supported Microsoft solution.
* Simplified Experience: Transitioning from cryptic MOF files to human-readable JSON templates, significantly lowering the learning curve for admins.
* Snapshot & Drift Detection: The ability to capture “snapshots” of your tenant’s current state and monitor for unauthorized changes.
* Automatic Remediation: Automatically reverting detected configuration drifts back to your defined “gold standard” state.
* Broad Coverage: Support for core workloads including Entra ID, Exchange, Intune, Purview, Defender, and Teams with more to come.
This isn’t just a new feature; it’s the evolution of tenant governance into a native, API-driven platform. Tune in to hear Nik explain how TCM is bridging the gap between community innovation and official enterprise-grade management.
Listen to the full episode now to learn how to start your journey with the TCM public preview!
Subscribe with your favorite podcast player or watch on YouTube 👇

About Nik Charlebois
Nik is a Principal Program Manager at Microsoft leading the Microsoft 365 configuration-as-code efforts. Ex-MVP, speaker, blogger, and author, he leads the configuration-as-code efforts for Microsoft 365.
LinkedIn - https://linkedin.com/in/nikcharlebois
🔗 Related Links
* Nik’s Blog - https://nikcharlebois.com/
* Overview of the unified tenant configuration management APIs - https://learn.microsoft.com/en-us/graph/unified-tenant-configuration-management-concept-overview
📗 Chapters
00:00 Intro
03:44 Origin of M365DSC
07:51 Introducing Tenant Config Management
09:24 Supported Workloads
11:15 Control Plane vs Data Plane
14:26 DSC vs TCM Architecture
15:22 Snapshots and Monitors
18:56 Managing Drift Across Environments
28:03 Licensing and Limits
32:48 Authentication and Permissions
37:53 Getting Started
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
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🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill


Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe

In this episode, we sit down with Eric Woodruff, Chief Identity Architect at Semperis, to discuss the reality of achieving a 100% phishing-resistant environment. Over the course of just three months, Eric led a 600-person organization through a complete rollout of passkeys, Windows Hello for Business, and Platform SSO. This conversation moves beyond the technical “knobs and dials” to explore why organizational change management and C-suite buy-in are the true foundations of a successful identity modernization project.
Eric shares the creative strategies his team used to drive adoption, including a custom self-enrollment portal built with Power Platform that allowed early adopters to “dogfood” the technology. We dive into the “voluntold” phase of the rollout, where voluntary participation transitioned into mandatory policy, and how they used Power BI to track progress and identify “stragglers”. The episode also provides a transparent look at the technical hurdles encountered, from legacy application exclusions to troubleshooting older Android devices and niche browsers.
Looking ahead, we discuss the critical importance of protecting against “downgrade attacks,” where sophisticated phishing attempts try to bypass modern security by tricking users into traditional password entries. Eric emphasizes that the final mile of this journey—removing passwords entirely—is as much about supporting your helpdesk and documenting processes as it is about the technology itself. Whether you are managing a cloud-only tenant or navigating complex hybrid scenarios, this episode offers a practical roadmap for the future of enterprise identity.
Subscribe with your favorite podcast player or watch on YouTube 👇

About Eric Woodruff
Throughout his 25-year career in the IT field, Eric has sought out and held a diverse range of roles. Currently the Chief Identity Architect for Semperis; Eric previously was a member of the Security Research and Product teams. Prior to Semperis, Eric worked as a Security and Identity Architect at Microsoft partners, spent time working at Microsoft as a Sr. Premier Field Engineer, and spent almost 15 years in the public sector, with 10 of them as a technical manager.
LinkedIn - https://www.linkedin.com/in/ericonidentity/
🔗 Related Links
* Phishing-resistant passwordless authentication deployment in Microsoft Entra ID
* Semperis Research Uncovers Ongoing Risk from nOAuth Vulnerability in Microsoft Entra ID, Affecting Enterprise SaaS Applications
* ConsentFix: Analysing a browser-native ClickFix-style attack that hijacks OAuth consent grants
* Meet Silver SAML: Golden SAML in the Cloud
* Manage tokens for Zero Trust
📗 Chapters
02:50 Rolling Out Passkeys
06:47 Application and Device Issues
09:49 Identifying Password Users
12:15 Lessons Learned for 2026
15:14 Understanding Downgrade Attacks
20:10 The NoAuth Vulnerability
27:08 Silver SAML Explained
32:56 Managing Service Principals
38:15 The Consent Fix Attack
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
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🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill


Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe

Service principals worked for static apps, but AI agents are different—they make autonomous decisions using LLMs and require a new approach to identity and security.
In this episode of Entra Chat, Padma Parthasarathy, Product Manager for Microsoft Entra Agent Registry, explains why Microsoft created Entra Agent Registry and Agent ID, and how they provide identity, governance, and security for AI agents.
We cover agent collections, discovery policies, integration with identity protection, and how custom security attributes automate AI agent governance at scale. You’ll also see how agents discover other agents by skills, how global and quarantine collections control visibility, and why these capabilities are critical for enterprise AI security.
This is a must-watch (listen) for identity, security, and platform architects preparing for AI at scale.
Subscribe with your favorite podcast player or watch on YouTube 👇

About Padma
With close to 20 years of experience in Identity, Security, and enterprise platforms, Padma Prasad Parthasarathy currently leads product and architecture for Security for AI and Agent Identity at Microsoft. He has built and scaled IAM and Zero Trust solutions across some of the world’s largest organizations, bridging deep technical expertise with real-world product impact.
LinkedIn - https://www.linkedin.com/in/padmaprasadp/
🔗 Related Links
* What is the Microsoft Entra Agent Registry? - https://learn.microsoft.com/en-us/entra/agent-id/identity-platform/what-is-agent-registry
📗 Chapters
00:00 Intro
02:14 The Rise of Digital Workers
07:13 Static Apps vs. AI Agents
12:43 Introducing Entra Agent Registry
17:28 Agent ID vs. Registry
24:08 How Agents Collaborate
30:29 Emerging Agent Standards
35:24 Understanding Agent Collections
42:05 Managing Risky Agents
46:01 Automating Agent Security
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill


Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe