Entra.Chat

At Black Hat USA 2026, Microsoft’s David Weston put three numbers on a slide that anyone still running domain controllers should sit with. The Microsoft Security Response Center went from 80 patches in February to 1,142 at the July Patch Tuesday. The fastest observed breakout time dropped from 98 minutes to 27 seconds. And mean time-to-exploit flipped from 63 days after a patch shipped to seven days before the patch existed.
Tarek Dawoud, Lead Architect on the Technical Excellence Team in Microsoft Security, walks Merill through those slides and then draws the conclusion for identity teams in his own words: “Active Directory is like 10x harder to defend than Entra.” If you do not already have a plan to move off AD, he says, sit down and write one.
He also says how Microsoft handles this itself. Most of Microsoft’s own servers run in the cloud, its front ends run with no domain at all, and on-prem AD survives mainly as a dial-tone service: the thing they need to bring Azure up from scratch, and not much else.
Tarek is back on Entra.Chat, and he was privy to a small part of Project Glasswing, where Microsoft got early access to Anthropic’s Mythos-class models to find vulnerabilities in its own products before attackers could. The red-team community was cynical at the time; what Microsoft saw internally was, in his words, “very concerning. Those things were damn good.” From there he builds Weston’s argument: the whole security industry rests on an assumption of scarcity. Vulnerabilities are rare, exploits are expensive, and attackers have recognisable tactics, techniques and procedures. Patch-and-pray works when bugs arrive slowly. TTP-based detection works when a human crew reuses its playbook. When a risk is small, driving it smaller is worth the money; as Tarek puts it, “if something has a 95% possibility of happening, pushing it down to 80% doesn’t change anymore.” The Hugging Face intrusion (an OpenAI agent, and not a deliberate attack, as Merill is quick to note) showed what happens when the old assumptions fail: the agent landed on one server and looped, try an exploit, fail, write a new tool, try again, with no attempt to hide and no signature to match. Hugging Face survived by repeatedly tearing down and rebuilding core infrastructure. Tarek’s question for listeners: “Does your AD team have that skill?” Tearing down and rebuilding domain controllers, he notes, is not a thirty-minute operation.
Hence the pitch: “Where you don’t need to own infrastructure, you shouldn’t manage infrastructure.” Tarek is explicit that this is his read of the moment rather than a mandate, and that it does not apply everywhere. Disconnected environments, military and intelligence, some manufacturing and IoT, and shielded OT networks such as utilities and remote mine sites are carved out; nobody is going to win the argument to punch a hole in an isolated OT environment to reach Entra. But for the ordinary case, collaboration, email, SharePoint, file shares, and apps that already live in Azure or AWS or even on-premises, he calls running your own identity infrastructure a losing battle. The minimum step is a strategy memo for your board that says what you are facing and why identity infrastructure investment needs to shrink.

Merill raises the two objections he hears most. First: you are just trusting Microsoft, and Entra ID has bugs too. Tarek’s answer is about who is on the hook. Microsoft owns and patches the Entra infrastructure; the service deploys roughly every 10 business days and can push a critical hotfix worldwide within a day or two, across a fleet that was already more than 100,000 compute nodes five years ago. You still have to handle Entra bugs, but the work looks like a Conditional Access policy to block a risky flow such as device code flow, not patching every server yourself. One customer he worked with had about 12 people in IAM for more than 200,000 employees; Entra has over 2,000. Second: this is licensing revenue and cloud stickiness dressed up as security. Tarek does not pretend to know the CAL math. “Assuming good intentions,” he says, the case is defensibility: the ports, the legacy protocols, the sheer number of things to watch, and the amount of legacy that is indefensible. That is where the “10x” line comes from: an architect’s rough comparison, not a measurement.
The back half is the path, using the Road to the cloud model at aka.ms/ad2entra. Map yourself to one of five states first: cloud attached, hybrid, cloud-first, AD minimized, cloud only. Then the moves that matter most. Decide, as a business, to stop buying apps that only run on-prem and make OAuth or SAML support a checkbox in the security review, because you will never turn off AD while a single LDAP app remains. Move devices to cloud management and out of hybrid join. Do not extend your domain into the cloud to manage servers; every cloud can patch and maintain a server without one, Microsoft’s own front ends run with no domain, and a domain you rely on becomes an attack vector for every server that trusts it. At the AD-minimized stage, HR provisions to Entra first (cloud HR, or API-driven inbound provisioning if your HR system is on-prem or file-based) and only the subset of users who need a stubborn legacy app is brought down to AD. The order of operations is apps first, then users and groups, with the Zero Trust Workshop identity pillar as the tracker for every box.
Tarek is honest about what is not solved. Intune does not manage servers today (Azure Arc is one approach), and some on-prem cases, such as retail stores that need local servers to keep point of sale running when the internet drops, still need a domain controller. The identity data warehouse, the layer that normalises HR data before it reaches the directory, is something SailPoint does well and Entra “doesn’t quite do yet,” so expect that MIM, SailPoint or Saviynt-style layer to persist. And the last two Exchange servers: object-level Source of Authority transfer exists now, but the attribute-level transfer that would let you switch just the mail properties to cloud management is still in progress. Tarek has met maybe five customers at stage 5. He still closes with hope. If the last thing standing before your domain controller is those two Exchange servers, you have succeeded, and “as someone who owns identity infrastructure, you do have a path out. There are people who have no path out.”
If you still own domain controllers and there is no written plan to stop, this episode is the memo.

What you will learn
* Why the scarcity assumption behind patching and TTP-based detection is breaking, and what the numbers on Weston’s slides (80 to 1,142 patches, 27-second breakout, exploits seven days before the patch) mean for anyone who owns servers.
* What the Hugging Face intrusion showed about how an AI agent actually attacks, and the one question to ask your AD team.
* How Tarek answers “Entra ID has bugs too” and “this is just licensing,” and what your residual burden looks like on an IDaaS.
* The five states of the Road to the cloud model, and why mapping where you are comes before any migration work.
* Why you do not need a domain to manage servers in the cloud, and where a domain controller is still legitimately needed.
* What changes at the AD-minimized state: HR to Entra first, API-driven provisioning for non-cloud HR, and why an identity data warehouse still exists.
* What actually keeps the last two Exchange servers alive, and how object-level versus attribute-level Source of Authority changes that.
* Which legacy protocols are the real blockers (NTLM and LDAP) and the options on the table: App Proxy, Entra Domain Services, Universal Print.
* How to use the Zero Trust Workshop identity pillar to track every step and stop the on-prem estate from growing.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Tarek Dawoud
Tarek Dawoud is Lead Architect on the Technical Excellence Team in Microsoft Security, part of the Microsoft Security Customer Value Program. A Microsoft veteran of more than 18 years, he previously led the architecture team in Microsoft’s customer engineering (CXE) organization for Microsoft Entra, and has worked with Microsoft’s largets enterprise customers on identity for years. He is a returning Entra.Chat guest; his earlier episode, From Active Directory to AI Agents: The 25-Year Saga of Microsoft’s Identity, is at https://entra.news/p/from-active-directory-to-ai-agents.
LinkedIn - https://www.linkedin.com/in/tarekdawoud/
Related Links
* David Weston’s Black Hat USA 2026 keynote, The End of Rare: Defending When Offense Is Cheap (mentioned at 05:42; Tarek suggests skipping the first 14 minutes to get to the talk) -
* Hugging Face: Anatomy of a Frontier Lab Agent Intrusion, a technical timeline of the July 2026 incident (mentioned at 13:51) - https://huggingface.co/blog/agent-intrusion-technical-timeline
* OpenAI: The Hugging Face incident and the road ahead (companion post to the Hugging Face timeline) - https://openai.com/index/hugging-face-incident-and-the-road-ahead/
* Road to the cloud: moving identity and access management from Active Directory to Microsoft Entra, aka.ms/ad2entra (mentioned at 26:14) - https://learn.microsoft.com/entra/architecture/road-to-the-cloud-introduction
* Cloud-based management of Exchange attributes for Remote Mailboxes in hybrid environments (mentioned at 51:08) - https://learn.microsoft.com/en-us/exchange/hybrid-deployment/enable-exchange-attributes-cloud-management
* Decommission the last Exchange Server after transferring SOA to cloud (mentioned at 51:08) - https://learn.microsoft.com/en-us/exchange/hybrid-deployment/decommission-last-exchange-server
* Microsoft Zero Trust Workshop video playlist, including the identity walkthrough (mentioned at 57:51) - https://www.youtube.com/playlist?list=PL3ZTgFEc7LyuZlK_W0nUN_VV6hscz-rQP
* Zero Trust Workshop guided videos (mentioned at 57:51) - https://microsoft.github.io/zerotrustassessment/docs/videos
* Zero Trust Workshop, identity pillar (mentioned at 52:21) - https://zerotrust.microsoft.com
* Matt Zorich’s post on how hard it is to recover a compromised on-prem environment (mentioned at 21:02) -
* Project Glasswing: securing critical software for the AI era (mentioned at 02:10) - https://www.anthropic.com/glasswing
* User Source of Authority (SOA) overview - https://learn.microsoft.com/en-us/entra/identity/hybrid/user-source-of-authority-overview
* Group Source of Authority (SOA) overview - https://learn.microsoft.com/en-us/entra/identity/hybrid/concept-source-of-authority-overview
* API-driven inbound provisioning concepts - https://learn.microsoft.com/en-us/entra/identity/app-provisioning/inbound-provisioning-api-concepts
* Overview of Microsoft Entra Domain Services - https://learn.microsoft.com/en-us/entra/identity/domain-services/overview
* What are cloud-native Windows endpoints - https://learn.microsoft.com/en-us/intune/solutions/cloud-native-endpoints/overview
* Windows Hello for Business cloud Kerberos trust deployment guide - https://learn.microsoft.com/en-us/windows/security/identity-protection/hello-for-business/deploy/hybrid-cloud-kerberos-trust
Related Entra.Chat Episodes
* How General Motors Moved 200,000 People to Passkeys - https://entra.news/p/how-general-motors-moved-200000-people
* They migrated 40,000 devices to Entra Join in 9 months - https://entra.news/p/they-migrated-40000-devices-to-entra
* Decommissioning On-Prem AD: Lessons Learned from We Are Era’s Successful Migration - https://entra.news/p/decommissioning-on-prem-ad-lessons
Chapters
00:00 Intro
01:30 Mythos and Glasswing
05:42 Weston’s Black Hat keynote: the end of scarcity
11:29 Pyramid of Pain and the Hugging Face intrusion
17:02 27-second breakouts and exploits before the patch
19:41 The pitch: get off AD
23:10 But Entra ID has bugs too
26:10 aka.ms/ad2entra and the licensing objection
31:38 Where to start: cloud attached to cloud first
34:47 What about servers? You don’t need a domain
41:20 AD minimized: cloud HR and the identity warehouse
47:23 Stage 5 and the last Exchange server
52:07 The Zero Trust Workshop identity pillar
57:54 Closing with hope
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

Microsoft starts making passkeys the default in Microsoft Entra ID on 1 September 2026, and retires Microsoft-provided SMS and voice MFA on 1 February 2027. Every organisation with a large, messy population now has to answer a question that has nothing to do with passkey technology itself: how do you move a hundred thousand real people - office workers, factory floors, call centres and guests - without locking someone out?
In this episode, Merill sits down with the person who has already done it. Andrew Cameron is a Distinguished Engineer for Identity and Cybersecurity at General Motors, and he has spent roughly 25 years there, long enough to have started on the employee portal as a web architect in 2000, and then helped build the identity function that now carries one of the world’s largest passwordless deployments.
The single biggest lever, Andrew says, was almost embarrassingly simple. GM treated Windows Hello as an optional convenience for years, then realised that an already-managed Windows device is a passkey. About 100,000 people were enabled through Windows Hello alone - no roaming key, no phone, no authenticator juggling. Platform SSO now extends the same idea to Mac through the secure enclave.
The sequence matters as much as the tools. Admin roles came first, required to carry a device-bound passkey with Azure PIM forcing the stronger method through activation. Then Conditional Access did the rollout: a small group of eager users, audit mode, and then add apps and expand outward. Andrew’s practical tip is to target the big, heavily used apps before chasing every user - it often gets you to 80% coverage faster.
Then the conversation turns to the corners most passkey explainers skip. Manufacturing workers who cannot use a phone and do not have a keyboard. Guest accounts - suppliers, dealerships and contractors - whose source tenant must also enable passkeys before the journey can complete. Call-centre users on unmanaged devices. And VDI, where certificate auth or Azure Virtual Desktop fills the gap.
Andrew also walks through the synced-versus-device-bound decision, and lands on the unglamorous first step of the whole thing: before you retire anything, know which authentication methods are actually in use.
If your plan for the SMS/voice deprecation is “we’ll deal with it in February,” consider this episode your head start.

What caught GM’s identity team by surprise
Andrew was candid about the corners that bit them - the ones most admins only discover after the weak method is already gone:
* SMS was the onboarding bootstrap. A new starter was never expected to have a passkey, so onboarding simply defaulted to an SMS code. Remove SMS and you have also removed the way people got in on day one. GM’s fix: issue a Temporary Access Pass (TAP) for onboarding, then register a strong method immediately.
* A new phone defaulted to SMS again. The “I just got a new phone” recovery path sent a code to the number by default. That whole flow had to be redesigned too, not just the sign-in policy.
* Guests were the hard problem. Several hundred thousand suppliers, dealerships and contractors can only finish a passkey sign-in if their own source tenant has also enabled passkeys. Enforce on your side and a guest can still get blocked upstream through no fault of yours.
* Factory floors have no phones and no keyboards. Manufacturing workers could not use a phone or type a password, so GM built custom non-password methods and used hardware keys for robots and other physical assets.
* Call-centre users are not on managed devices. Tens of thousands of users were remote or unmanaged, so GM folded device posture and network location into the risk evaluation.
* VDI was a fresh corner. Certificate auth and Azure Virtual Desktop SSO replaced SMS as the way into a virtual desktop.
* Hardware-key attestation had to be unwound. GM had registered AAGUIDs for hardware keys; when synced passkeys arrived, those old attestation requirements no longer applied and had to be revisited.
GM’s secrets: don’t repeat the mistakes
* Your managed device is already a passkey. The light-bulb moment was realising Windows Hello turns an already-managed Windows device into a passkey — no phone required. It became the fast path for roughly 100,000 people, and Platform SSO does the same on Mac.
* Privileged roles first, then everyone else. Admin roles carried device-bound passkeys, with Azure PIM forcing the stronger method through activation.
* Use Conditional Access as the rollout engine. Small pilot group → audit mode → add apps → expand. No big bang.
* Target the big apps, not every user. You reach ~80% coverage faster by protecting the heavily used apps first, then adding more to the same policy.
* Know your authentication methods before you retire anything. Monitoring and visibility come first — the deprecation clock is not the plan.
Sponsored by:
Scan, Score, and Secure Your Applications in Entra

Application identities represent one of the largest attack surfaces in Entra — and often one of the least consistently governed. AppGov Score helps IT and security teams understand where that risk sits.
The 24-check assessment evaluates your Entra ID application integrations against Microsoft-recommended governance practices, analyzing:
* App registrations and enterprise apps for excessive permissions
* Expired or unmanaged secrets
* Ownerless apps
* Risky consent grants
* Privileged service principals
Results are delivered as a clear, defensible risk score with actionable findings. No scripts. No manual inventory. Just a fast, read-only scan that reveals app sprawl, identity misconfigurations and blast radius — so you can prioritize remediation and strengthen your security posture with confidence.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Andrew Cameron
Andrew Cameron is a Distinguished Engineer for Identity and Cybersecurity at General Motors. He joined GM in 2000 as a web architect working on the employee portal, then moved into directory services and helped stand up GM’s identity and access management team in 2004. He has spent the past quarter-century building and leading identity and security at one of the world’s largest manufacturers from early SAML and OpenID Connect standardisation and Azure AD adoption, to GM’s current passwordless rollout across roughly 200,000 people.
LinkedIn - https://www.linkedin.com/in/kandrewcameron/
Related Links
* Passkeys by default and retirement of Microsoft-provided SMS and voice authentication (mentioned at 13:23) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement
* Passkeys (FIDO2) authentication in Microsoft Entra ID (context throughout) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2
* Synced passkeys, device-bound passkeys and passkey profiles (discussed at 33:57) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2
* Deploy phishing-resistant passwordless authentication (context at 28:38) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
* Configure a Temporary Access Pass (discussed at 12:48 and 33:20) - https://learn.microsoft.com/entra/identity/authentication/howto-authentication-temporary-access-pass
* Windows Hello for Business (the fast path discussed at 09:32 and 26:24) - https://learn.microsoft.com/windows/security/identity-protection/hello-for-business/
* Configure Platform SSO for macOS devices (discussed at 27:23) - https://learn.microsoft.com/intune/device-configuration/settings-catalog/configure-platform-sso-macos
* Require device compliance with Conditional Access (unmanaged-device discussion at 41:35) - https://learn.microsoft.com/entra/identity/conditional-access/policy-all-users-device-compliance
Related Entra.Chat Episodes
* 5 Lessons from Rolling Out Passkeys to Millions of Users - https://entra.news/p/5-lessons-from-rolling-out-passkeys
* From SMS MFA to Passkeys: A Practical Microsoft Entra Migration Plan - https://entra.news/p/from-sms-mfa-to-passkeys-a-practical
* Mastering Microsoft Entra ID: Real-World Passkey Deployment Tips - https://entra.news/p/mastering-microsoft-entra-id-real
Chapters
00:00 Intro
00:27 Meet Andrew Cameron
01:34 25 years of identity at GM
07:34 200,000 people and their personas
08:24 The strategy: passkeys over weaker MFA
09:32 Windows Hello: the fast path
10:06 Factory floors and hardware keys
11:20 Sponsor: AppGov Score
13:23 The SMS and voice deprecation
14:20 The guest-account problem
20:30 Roadblocks: onboarding and new phones
23:30 Conditional Access: small groups first
25:02 VDI, certificate auth and Azure Virtual Desktop
27:23 Platform SSO on Mac
28:38 The playbook: monitor, target, measure
33:57 Synced vs device-bound passkeys
35:35 Privileged roles first and Azure PIM
38:54 Final thoughts and wrap-up
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

On 3 November 2026, the memberOf operator in Microsoft Entra dynamic membership groups stops working. Nothing errors. Nothing breaks loudly. Every dynamic group, dynamic administrative unit and entitlement management auto-assignment policy that uses it simply freezes in its last known state the people who should be added are not added, and the people who should be removed stay.
It was a preview feature for four years. It is in a lot of production tenants.
In this episode of Entra.Chat, Merill is joined by three guests for the first time: Gregor Reimling, Chief Azure Technologist at adesso SE and Microsoft MVP for Azure and Security; René Wasel, a Microsoft 365 specialist and Microsoft MVP; and returning guest Eric Woodruff, Chief Identity Architect at Semperis. Gregor and René co-organise the Cloud Identity Summit, which happens to fall on the same date the deprecation lands.
The conversation starts with the deadline and quickly becomes something more useful: an honest audit of what groups in Entra actually do, versus what administrators assume they do.
The memberOf operator existed because Entra does not resolve nested groups the way Active Directory does. It was a flattening trick — take the members of several groups and produce one flat group that applications, licensing and policies could read. With it going away, the panel walks through the realistic replacements: move to supported attribute-based rules where an attribute exists, stamp an attribute with PowerShell where one does not, or convert the group to assigned membership and script it. Gregor and René both raise the version of this that is easy to forget — a rule written years ago that nobody documented, using a sync rule editor nobody wants to reopen.
Then the discussion turns to the part that is not on any deprecation notice. Nested groups are supported in Conditional Access. They are not supported for group-based licensing, where only first-level members get a licence. They are not supported for Global Secure Access, where a nested group assigned to a traffic forwarding profile applies only to its direct members with no error, no warning, and nothing in the portal to tell you. Chris Brumm found that one and wrote a Maester test for it, because the only way to know is to go looking.
There is a new group property that blocks nesting in both directions, undocumented when this was recorded. Sensitivity labels have reached Entra security groups in preview, bringing a guest-access control that stops new guests but does not evict the ones already in the group. And Merill spotted something through Entra.News Daily that deserves more attention than it has had: an agent’s user account is a user identity, so existing dynamic user rules already evaluate it. If your licensing group has a broad rule and your developers start creating agent accounts, those accounts qualify. If it is a group behind a Conditional Access policy or an exclusion, that is a different conversation entirely.
Which leads to the sharpest point in the episode, and Eric makes it plainly: the security of a dynamic group is the security of the write permissions on the attributes in its rule. Some of those attributes are self-service. Some flow up from on-premises Active Directory, changed by people who are not thinking about the cloud at all. Microsoft Learn now carries an explicit warning about exactly this, and it is why groups used for privileged access cannot be dynamic.
The last third is about the Cloud Identity Summit itself. More info below.
If you have memberOf in a rule anywhere, the useful thing to do this week is find it. Everything else in this episode can wait until after November.
Featured sponsor
Cloud Identity Summit 2026 → One Day, One Topic, In the Room
Identity. Security. 2026. On Tuesday 3 November in Frankfurt, the Cloud Identity Summit gives cloud identity a conference of its own, now in its seventh year, and free to attend.
Two parallel tracks, Identity Management and Identity Security, run 50-minute sessions in English. It is deliberately vendor-neutral: Microsoft Entra, AWS, Google Cloud and whatever else you actually run. Eric Woodruff keynotes with Identity Security Kindergeburtstag fourteen years of identity being called “the new security perimeter”, and an honest look at what that has actually got us.
Why it is worth the trip:
* It is in person only. No livestream, no catch-up recordings. The organisers built it that way on purpose — “a strong focus on face-to-face conversations to support networking and exchange of experiences.” If you want the hallway conversation, you have to be in the hallway.
* Everything is identity. No filler tracks. A whole day of people who work on the same problems you do, from an international mix of industries.
* The Community Ticket is 100% free. There is an optional paid Supporter Ticket if you want to help fund the event.
* It is easy to get to. adesso SE, Prisma Frankfurt-Niederrad — around ten minutes by S-Bahn from Frankfurt Airport, ten from Frankfurt Hauptbahnhof, and a short walk from Frankfurt-Niederrad station.
* Travelling in? The Crowne Plaza Frankfurt is a ten-minute walk, €89 single with breakfast on the “Cloud Identity Summit” booking code — 50 rooms, held until 5 October.
One more thing, given what this episode is about: 3 November is also the day Microsoft retires the memberOf operator. If you are going to spend that Tuesday thinking about Entra groups anyway, spend it in a room with people solving the same problem.
Subscribe with your favorite podcast player or watch on YouTube
About Gregor Reimling
Gregor is a Microsoft MVP in Azure and Security, Chief Azure Technologist at adesso SE, and a passionate advocate for the Microsoft cloud community. His expertise spans Azure architecture, Microsoft Entra, Zero Trust and hybrid cloud environments; he helps organizations successfully navigate their cloud journey. Beyond his day job, Gregor is a frequent speaker at international events, co-host of the Cloud Inspires podcast and co-founder of the Cloud Identity Summit. As a Microsoft Certified Trainer, he enjoys sharing knowledge, mentoring others, and helping IT professionals get the most out of Microsoft technologies.
LinkedIn - https://www.linkedin.com/in/gregorreimling/
About René Wasel
René is a Microsoft 365 specialist, and a Microsoft MVP for Microsoft 365. He describes his work as helping people actually use the technology they have been given, and he is active in the community as a meetup and event organiser. He co-organises the Cloud Identity Summit.
LinkedIn - https://www.linkedin.com/in/renewasel/
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
* MC1448379 - Microsoft Entra ID: Replace MemberOf rules by November 3, 2026 - https://mc.merill.net/message/MC1448379
* Entra.News Daily, Merill’s daily diff of Microsoft Entra documentation changes (mentioned at 26:26) - https://daily.entra.news/changes/2026-08-14/manage-rules-for-dynamic-membership-groups-in-microsoft-entra-id-16/
* Maester, the open-source test framework used for the dynamic-group and nested-group checks discussed (mentioned at 06:09 and 30:06) - https://maester.dev/contributors/agnivesh
* Configure dynamic membership groups with the memberOf operator - the official retirement notice and migration guidance - https://learn.microsoft.com/entra/identity/users/groups-dynamic-rule-member-of
* Manage rules for dynamic membership groups - covers agent user accounts and the attribute write-permission warning - https://learn.microsoft.com/entra/identity/users/groups-dynamic-membership
* Assign users and groups to Global Secure Access traffic forwarding profiles - confirms nested groups are not supported (discussed at 15:50) - https://learn.microsoft.com/entra/global-secure-access/how-to-manage-users-groups-assignment
* Group-based licensing - confirms only first-level members receive licences - https://learn.microsoft.com/entra/fundamentals/concept-group-based-licensing
* Assign sensitivity labels to Microsoft Entra security groups (preview) (discussed at 25:09) - https://learn.microsoft.com/entra/identity/users/groups-sensitivity-labels
* Eric’s Cloud Identity Summit keynote, “Identity Security Kindergeburtstag” (mentioned at 34:12) - https://www.identitysummit.cloud/speaker
Related Entra.Chat Episodes
* Operational Groups in Entra with Nathan McNulty - https://entra.news/p/operational-groups-in-entra-with
* Mastering Microsoft Entra ID: Real-World Passkey Deployment Tips - Eric’s previous episode, referenced at 02:12 - https://entra.news/p/mastering-microsoft-entra-id-real
* From Active Directory to AI Agents: The 25-Year Saga of Microsoft’s Identity - the keynote-turned-podcast Merill promised to link (mentioned at 40:16) - https://entra.news/p/from-active-directory-to-ai-agents
Chapters
00:00 Intro
01:17 Meet Gregor, René and Eric
02:12 Passkeys: what comes after the rollout
04:17 memberOf is being retired
06:45 Workarounds: attributes, PowerShell and sync rules
10:41 Why Entra wants your groups flat
14:36 Where nested groups silently fail
17:45 The new property that blocks nesting
19:27 AD-sourced groups vs Entra-sourced groups 25:09 Sensitivity labels come to security groups
26:23 Agents are already in your dynamic groups
28:23 Why dynamic groups are not a security control
31:31 Inside the Cloud Identity Summit
35:21 Identity is not the “new” perimeter
41:44 November 3, tickets and wrap-up
Podcast Apps
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

Passkeys are phishing-resistant. But that resistance is enforced by your browser, which binds every authentication to the origin that requested it. Skip the browser, and the guarantee weakens.
In this episode of Entra.Chat, I spoke with Michael Grafnetter, Principal Security Researcher at SpecterOps and Microsoft MVP, about the Pass-the-Passkey research he presented at Black Hat USA 2026. A family of attacks against passkey implementations across Windows, Microsoft Entra ID, browsers and password managers.
Michael starts with the vulnerability chain he reported to Microsoft. Windows was writing the complete passkey assertion into the event log, and Microsoft Entra ID would accept a replay of that assertion for up to ten minutes. Any user able to read those logs including a member of Remote Desktop Users on a shared server, or unprivileged malware quietly reading event logs without tripping EDR could impersonate whoever had just signed in. If that person was a Global Administrator, so was the attacker. Windows now truncates the logged message, and Microsoft Entra ID checks authenticator signature counters to reject replays.
One clarification Michael is emphatic about: private keys were never written to the event log. They stay bound to the TPM or never leave the security key at all. What leaked were the short-lived digital signatures made by those keys and for this attack, that was enough.

We also covered the attacks that do not depend on any single bug. Malware running without administrator rights can call the native Windows WebAuthn APIs directly and raise a passkey prompt flood that keeps returning until the user gives in and approves it. Synced passkeys, exported from a password manager and decrypted with a keylogged password, hand an attacker a credential with no ten-minute limit at all. And a browser-hooking technique Michael calls a passkey detour attack quietly redirects a legitimate assertion into the attacker’s own session.
The defensive thread running through all of it is the same: every one of these attacks assumes malware is already on the device. That makes device trust the key control. Privileged access workstations for administrators, Conditional Access requiring compliant devices with EDR running, and the clean source principle that says a system can only be as trustworthy as whatever it depends on.
Michael closes on an optimistic note, and it is worth repeating. Passkeys are still the future. They remain far better than passwords and phishable MFA, and every attack here costs an adversary vastly more effort than sending a phishing link. But as passkeys become the default in Microsoft Entra, the threat model deserves an honest read.
Watch the demos. This episode includes three on-screen demonstrations that are much easier to follow on video than on audio.
This episode brought to you by Workplace Ninjas US
Workplace Ninjas US isn’t just another tech conference. It’s where Microsoft experts, MVPs, engineers, and IT professionals come together to learn, network, and build lasting connections.
We are a community built on diversity, mentoring, fellowship, and creating a place where everyone belongs.
Our core DNA comes down to a few pillars:
* Over 60 sessions from the largest collection of MVPs and SMEs you will find in any event in America.
* Amazing mentoring, development, and growth through our one on one mentoring system with any speaker, our hackathon, community theatre and more.
* A diverse expo hall featuring some of the best Microsoft partners in the world that will help you drive deep efficiencies from your M365 stack.
* A place where you will learn how to think differently and collaborate better through a collection of activities and can return refreshed and invigorated to drive change in your organization.
* Don’t miss out on our early bird tickets while supplies last
Subscribe with your favorite podcast player or watch on YouTube
About Michael Grafnetter
Michael Grafnetter is a Principal Security Researcher at SpecterOps and a Microsoft MVP, based in Prague. He specializes in Microsoft Entra ID and Active Directory security and PowerShell. He is the author of the DSInternals PowerShell module and the researcher who originally discovered the Shadow Credentials attack technique, now widely used by penetration testers, red teamers and attackers alike. He has presented his security research at international conferences including Black Hat Europe, Black Hat USA, SecTor, TROOPERS and BSides Lisbon.
* LinkedIn - https://www.linkedin.com/in/grafnetter/
Related Links
* Pass-the-Passkey research and tools, including Passkey Injector and the DSInternals.Passkeys module (discussed at 14:57 and 34:22) - https://github.com/SpecterOps/pass-the-passkey
* Pass-the-Passkey research paper from Black Hat USA 2026 (introduced at 07:34) - https://specterops.io/wp-content/uploads/sites/3/2026/08/Pass-the-Passkey_A4_v2.pdf
* Shadow Credentials, Michael’s earlier Active Directory research (mentioned at 01:46) - https://specterops.io/blog/2021/06/17/shadow-credentials-abusing-key-trust-account-mapping-for-account-takeover/
* DSInternals PowerShell module (mentioned at 01:34) - https://www.dsinternals.com/en/
* Passkeys (FIDO2) authentication in Microsoft Entra ID (context throughout) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2
* Synced passkeys, device-bound passkeys and passkey profiles (discussed at 23:21) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2
* Deploy phishing-resistant passwordless authentication (context at 18:08) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
* Require device compliance with Conditional Access (recommended at 21:12) - https://learn.microsoft.com/entra/identity/conditional-access/policy-all-users-device-compliance
* Privileged access devices and the clean source principle (discussed at 21:55 and 35:41) - https://learn.microsoft.com/security/privileged-access-workstations/privileged-access-devices
* Unit 42, “Pass the Passkey: A Novel Attack Surface in Passwordless Authentication” — the Palo Alto research on Google Password Manager passkeys (mentioned at 26:27) - https://unit42.paloaltonetworks.com/passwordless-authentication-security-risks/
Related Entra.Chat Episodes
* From SMS MFA to Passkeys: A Practical Microsoft Entra Migration Plan - https://entra.news/p/from-sms-mfa-to-passkeys-a-practical
* 5 Lessons from Rolling Out Passkeys to Millions of Users - https://entra.news/p/5-lessons-from-rolling-out-passkeys
* Attackers Are Targeting The AI Ecosystem You Cannot See - https://entra.news/p/attackers-are-targeting-the-ai-ecosystem
Chapters
00:00 Intro
01:02 Meet Michael Grafnetter
03:09 How the Research Started
06:50 Windows Hello for Business Was the First Passkey
07:30 The Signature in Your Event Log
10:18 No, Private Keys Are Not Logged
12:25 How Entra Mitigated the Replay
13:44 Demo: Signing In With a Stolen Signature
15:22 Malware-Initiated Passkey Phishing
18:08 The Browser Is What Makes Passkeys Phishing-Resistant
20:42 What Defenders Should Actually Do
23:04 Synced Passkeys and the Export Problem
26:13 Credential Exchange and Password Manager Risk
28:19 The Passkey Detour Attack
30:43 The Authentication Broker Debate
31:57 RDP Redirection and Remote Passkey Abuse
32:59 Spotting a Suspicious Passkey Prompt
34:46 Passkeys Are Still the Future
Podcast Apps
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

Microsoft-managed SMS and voice MFA will stop working on February 1, 2027. That deadline makes passkey planning urgent, but enabling a new authentication method is only the first milestone.
In this episode of Entra.Chat, Merill speaks with Jai Maharaj, Product Manager at Microsoft, about the practical journey from legacy MFA to a passwordless Microsoft Entra environment. Jai explains what is actually being retired, why organizations can still use a customer-managed telecom provider, and how passkey profiles support synced and device-bound passkeys for different user personas.
The user-experience case is compelling: Microsoft reports roughly 69 seconds for password plus traditional MFA compared with about three seconds for a synced passkey. The security case is stronger still. Passkeys resist phishing by design, but Jai stresses that deploying them does not make an organization phishing-resistant until it enforces the right authentication strength and addresses the passwords and legacy applications still in the environment.
The conversation then follows the complete identity lifecycle. How do you ensure the right person receives a passkey during onboarding? How do you verify someone requesting a sensitive role? How do you recover an account without relying on knowledge-based help-desk questions? Jai connects those scenarios to Microsoft Entra Verified ID, verifiable credentials, Face Check, identity verification partners, and self-service account recovery.
Sponsored by
Scan, Score, and Secure Your Applications in Entra
Application identities represent one of the largest attack surfaces in Entra and are often among the least consistently governed. ENow AppGov Score helps IT and identity teams understand where risk exists. Its 25-check assessment evaluates Entra ID application integrations against Microsoft-recommended governance practices, analyzing:
* App registrations and enterprise apps for excessive permissions
* Expired or unmanaged secrets and certificates
* Risky consent grants
* Privileged service principals
Results are delivered as a clear, defensible risk score with actionable findings. No scripts. No manual inventory. Just a fast, read-only scan that reveals app sprawl, identity misconfigurations, and blast radius so you can prioritize remediation and strengthen your security posture.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Jai Maharaj
Jai Maharaj is a Senior Product Manager at Microsoft. He works with customers and engineering teams across Microsoft Entra, with experience spanning ID Governance, Verified ID, External ID, and passkeys. He helps enterprise and public-sector organizations move from legacy authentication methods to phishing-resistant authentication.
* LinkedIn - https://www.linkedin.com/in/jai-maharaj-0938305a/
Related Links
* Microsoft-managed SMS and voice retirement timeline (discussed at 02:19 and 06:31) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement
* Customer-managed telecom provider FAQ (mentioned at 03:41 and 07:13) - https://learn.microsoft.com/entra/identity/authentication/phone-providers-faq
* Passkey profiles, synced passkeys, and device-bound passkeys (discussed at 09:44) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2#passkey-profiles
* Passkey concepts and Microsoft performance figures (mentioned at 14:22) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2#what-are-passkeys
* Microsoft Entra Verified ID Face Check (introduced at 31:57) - https://learn.microsoft.com/entra/verified-id/using-facecheck
* ASD/ACSC Essential Eight maturity model (mentioned at 33:41) - https://www.cyber.gov.au/business-government/asds-cyber-security-frameworks/essential-eight/essential-eight-maturity-model
* Microsoft Entra account recovery overview (discussed at 36:59) - https://learn.microsoft.com/entra/identity/authentication/concept-account-recovery-overview
* Verified ID identity verification partners (discussed at 37:12) - https://learn.microsoft.com/entra/verified-id/idv-partners
* Microsoft Entra licensing (discussed at 39:27) - https://learn.microsoft.com/entra/fundamentals/licensing
* Verified ID and Face Check pricing model (discussed at 39:27) - https://learn.microsoft.com/entra/verified-id/verified-id-pricing
* Deploy phishing-resistant passwordless authentication (mentioned at 52:34) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
Related Entra.Chat Episodes
* Microsoft Is Auto-Enabling Passkeys in March 2026 - https://entra.news/p/microsoft-is-auto-enabling-passkeys
* Mastering Microsoft Entra ID: Real-World Passkey Deployment Tips - https://entra.news/p/mastering-microsoft-entra-id-real
* Entra Ignite Recap: Synced Passkeys, Agent ID & The Future of Identity - https://entra.news/p/entra-ignite-recap-synced-passkeys
Chapters
00:00 Intro
02:19 Why Microsoft Is Retiring Managed SMS and Voice
03:32 What the February 2027 Deadline Means
09:27 Synced vs Device-Bound Passkeys
14:22 From 69 Seconds to Three
19:02 Making Passkeys Easier for Users
23:14 Customer Passkey Deployment Lessons
28:41 The Secure Bootstrapping Problem
31:57 Verified ID and Face Check
33:41 Essential Eight and High-Value Access
36:24 Self-Service Account Recovery
39:27 Licensing and Recovery Economics
44:45 Why Face Check Augments Passkeys
49:40 Enforce Phishing Resistance and Build a Roadmap
Podcast Apps
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