Entra.Chat

AI agents are arriving in every Microsoft 365 tenant, and the questions admins ask first are what they cost to run and what it costs to secure them. In this Workplace Ninjas US special, four of the event’s speakers answer from the field: Jon Towles, founder of Workplace Ninjas US, Intune and AI tool builder Ugur Koc, Microsoft 365 security MVP Ru Campbell, and Spencer Alessi, the pen tester who defends Active Directory against Merill in the event’s AD vs Entra cage match.

Key takeaways

AI agents: cheap to run, not free to secure

* Admin agents can run on a laptop. You don’t need Security Compute Units, an E7 licence and Agent 365 just to query Microsoft Graph and reason over the results. Ugur’s answer is a local model that runs on a device with 8 GB of memory. His open-source OpenAdminOS runs agents as readable YAML files, top to bottom, through an MCP server and a local model such as Qwen on Ollama. “You don’t need like 10 SCUs to query your defender portal.”

* Review the tools you vibe-code before you share them. Ugur ran an agent-led security review over the new community projects for AwesomeIntune, found enough issues that he sent the authors fixes, and only published once they were merged. Keep API keys and secrets out of your repos, and treat every MCP connection as something to secure.

* An agent identity is free; securing it isn’t. Microsoft Entra Agent ID, with agent identities and blueprints, is available to every Entra customer. Conditional Access for agents needs Microsoft 365 E7, or Microsoft Agent 365 with at least Entra ID P1 or Microsoft 365 E3. Jon’s warning from the field: when the people using an agent don’t have Agent 365, “it’ll bypass conditional access when it talks to things like graph”. Budget for the licence before the agents go live.

Fix the baseline with one policy

* Block everything that isn’t on a managed device. Ru’s opening move when he hardens a new tenant: one Conditional Access policy for all users and all resources that requires a device marked as compliant or Microsoft Entra hybrid joined. “That’s the cheat code to securing Microsoft 365.” Start it in report-only and exclude your break-glass accounts.

* Know what each licence adds. Entra ID Free gives you security defaults. Entra ID P1, included in Business Premium, adds Conditional Access and the cheat code. E5 adds risk-based policies with P2. E7 matters once you add agents, because it includes Agent 365.

Cloud-native devices aren’t cloud-native identity

* Treat devices and identity as two decisions. Entra joined, Intune-managed devices work with users synced from Active Directory and can still reach file shares and Kerberos apps on-premises. Going cloud-only for identity is a separate, bigger step, and it’s the question behind the AD vs Entra debate.

* While AD is still there, keep defending it. Spence, a pen tester who talks mostly about Active Directory, is a fan of Entra and works in it every day. Plenty of tenants will run both for years, so follow the people who know AD as well as the ones who know Entra.

Watch the full conversation for how a Twitter fight became a conference session, the AD vs Entra scorecard, why Jon gives everyone an open bar and a puppy kennel, the 5K for Parkinson’s research, and who will still be running when the apocalypse comes. Explicit language.

Workplace Ninjas US 2027 runs 11-13 January 2027 at The Scott Resort & Spa in Scottsdale, Arizona. Tickets: workplaceninjas.us.

Sponsored by:

ENow Software Introduces New Entra ID App Onboarding Experience

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* Evaluate security risks more efficiently with integrated Microsoft Defender for Cloud Apps risk scores.

* Reduce manual work with centralized requests, reviews, and approvals.

* Improve transparency with a self-service portal for requesters to track status and decisions.

* Control app sprawl with an Internal App Catalog of approved applications.

Go beyond Microsoft’s consent and approval capabilities with customizable, structured application governance, from the initial request through ongoing oversight.

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See It In Action: Request a Demo

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About the guests

Jon Towles (”Mobile Jon”) is the founder of Workplace Ninjas US, an end-user computing practitioner with a long background in identity, and a Microsoft MVP.

→ mobile-jon.com | linkedin.com/in/jontowles

Ugur Koc builds free community tools for Microsoft Intune admins, including AwesomeIntune, IntuneBrew and IntuneAssignmentChecker, and is the creator of OpenAdminOS, an open-source desktop app for running local AI agents against Intune, Entra and Defender. He’s based in Hamburg, Germany.

→ ugurkoc.de | linkedin.com/in/ugurkocde

Ru Campbell is a Microsoft 365 security, compliance, identity and management expert and Microsoft MVP, based in Scotland. At Workplace Ninjas US he co-presents a Conditional Access session and hardens an out-of-the-box tenant live in 60 minutes.

→ campbell.scot | linkedin.com/in/rlcam

Spencer Alessi (”TechSpence”) is a Senior Penetration Tester at SecurIT360 and a Microsoft MVP (Security - Identity & Access). A recovering sysadmin turned pen tester, he writes and talks about Active Directory security and builds free tools such as ScriptSentry, ADeleginator and AppLocker Inspector.

→ spenceralessi.com | linkedin.com/in/spenceralessi

Related Links

From the conversation:

* Workplace Ninjas US 2027, 11-13 January 2027, Scottsdale, Arizona (mentioned at 02:58 and 24:41) - workplaceninjas.us

* Workplace Ninjas US agenda (Ru’s sessions and the AD vs Entra cage match; the agenda loads from the event platform) - https://workplaceninjas.us/agenda/

* AwesomeIntune: free Intune community tools (mentioned at 05:43) - awesomeintune.com

* OpenAdminOS: local-first AI agents for IT administration (mentioned at 07:03) - openadminos.com

* OpenAdminOS on GitHub - https://github.com/OpenAdminOS/OpenAdminOS

* Ollama: run models locally (mentioned at 07:12) - ollama.com

* Qwen models (mentioned at 07:13) - qwen.ai

* Spencer Alessi’s site and Ethical Threat Insights (mentioned at 16:39) - spenceralessi.com

AI agents and licensing:

* Microsoft Security Copilot Security Compute Units and capacity (mentioned at 09:09) - https://learn.microsoft.com/en-us/copilot/security/security-compute-units-capacity

* Conditional Access for agent identities, licensing requirements (mentioned at 09:39) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/agent-id

* What are agent identities? Microsoft Entra Agent ID (mentioned at 10:08) - https://learn.microsoft.com/en-us/entra/agent-id/what-are-agent-identities

* Overview of Microsoft Agent 365 - https://learn.microsoft.com/en-us/microsoft-agent-365/overview

Conditional Access baseline:

* Require device compliance with Conditional Access (mentioned at 11:46) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/policy-all-users-device-compliance

* Conditional Access: Grant controls - https://learn.microsoft.com/en-us/entra/identity/conditional-access/concept-conditional-access-grant

* Conditional Access policy templates - https://learn.microsoft.com/en-us/entra/identity/conditional-access/concept-conditional-access-policy-common

* Microsoft Entra licensing (mentioned at 11:58) - https://learn.microsoft.com/en-us/entra/fundamentals/licensing

* Security defaults in Microsoft Entra ID (mentioned at 12:25) - https://learn.microsoft.com/en-us/entra/fundamentals/security-defaults

Devices, identity and naming:

* Microsoft Entra joined vs hybrid joined in cloud-native endpoints (mentioned at 14:55) - https://learn.microsoft.com/en-us/intune/solutions/cloud-native-endpoints/entra-join-types

* How SSO to on-p…

Most SaaS vendors connect to your tenant with one multitenant app and one credential, shared by every customer. Kelvin Tegelaar, founder of CyberDrain and creator of CIPP (used by well over 10,000 MSPs), sees it from both sides, and his verdict is blunt: “This app is dangerous, period.”

Recorded on 14 October 2026, one day before the ConnectWise Cloud Backup app’s credential was used to sign in to customer tenants (173 confirmed by Huntress).

Key takeaways

The risk: one app, every tenant

* One app registration, a service principal in every tenant. The credentials sit on the vendor’s app registration, so one leaked secret or certificate works in every tenant that consented, with whatever application permissions you granted. For MSP tools, GDAP widens it to every customer behind the partner.

* You can’t put Conditional Access on a vendor’s app. Conditional Access for workload identities covers single-tenant apps only. Watch vendor apps’ sign-ins, ask vendors how they protect their credentials, and know where the Enabled for users to sign-in? switch is so you can disable an app fast.

Fix the credentials

* Retire client secrets; let certificates rotate themselves. Prefer managed identity or federation; otherwise use short-lived certificates. CIPP’s last 30 days and are replaced every two weeks with Microsoft Graph addKey/removeKey, not by granting the app Application.ReadWrite.All.

* Turn on app management policies. Block new client secrets and cap credential lifetimes. The tenant default policy is off until you enable it.

* Lock your app’s service principals. Builders: keep app instance property lock on (the default for new apps since June 2026), so customer tenants can’t add their own credentials to your app.

Fix the architecture

* Build one app per customer tenant. A leak in tenant A then stays in tenant A. It costs some engineering; one central app is “choosing convenience”, which is fine only if you choose it knowingly.

* Keep the apps you ship out of your corporate tenant. Separate tenants for corporate, Azure and the apps you publish, all secured to the same baseline. Decide early: an app registration can’t move between tenants.

Watch the full conversation for how Kelvin built CIPP out of spite, the vendor mistakes he sees most, and why a standard pen test won’t find any of this.

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Know what’s in your tenant, and keep watching it

Every risk above lives in your own tenant: multitenant vendor apps with powerful permissions, client secrets and certificates that live for years, and app management policies nobody turned on. Maester, the free, open-source security test framework for Microsoft 365, finds them, with tests for long-lived app certificates, expiring credentials, privileged permissions nobody uses and app management restrictions.

Maester Cloud keeps watching after the first scan:

* Continuous monitoring: scheduled runs, each one diffed against the last, with drift alerts sent from your own Microsoft 365 mailbox.

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* Every tenant in one place, switching between customers without signing in again. Unlimited users and tenants.

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About Kelvin Tegelaar

Kelvin Tegelaar is the founder of CyberDrain and the creator of CIPP, the CyberDrain Improved Partner Portal, an open-source, sponsor-funded tool that MSPs use to manage their customers’ Microsoft 365 tenants. He owns and is CTO of Lime Networks, an MSP in the Netherlands, and has been a Microsoft MVP for eight years. A system administrator rather than a developer by trade, he built CIPP in PowerShell and has blogged at CyberDrain.com for years about automating Microsoft 365 for MSPs.

GitHub - https://github.com/KelvinTegelaar

CyberDrain - cyberdrain.com

Related Links

From the conversation:

* Kelvin’s “accidental SaaS” blog post (mentioned at 02:25) - Referenced in the episode, but the blog post could not be found.

* Huntress: Never Just One Termite, 6 months of researching OAuth application attacks (rogue apps) (mentioned at 24:28) - https://www.huntress.com/blog/never-just-one-termite-6-months-of-researching-oauth-application-attacks

* Huntress: Traitorware, how hackers abuse legitimate apps to hijack Microsoft 365 - https://www.huntress.com/resources/traitorware-how-hackers-abuse-legitimate-apps-to-hijack-microsoft-365

* CIPP - cipp.app

* CIPP documentation - docs.cipp.app

* CIPP on GitHub - https://github.com/KelvinTegelaar/CIPP

* CyberDrain - cyberdrain.com

* Automating with PowerShell: making stolen tokens useless with Global Secure Access, by Kelvin Tegelaar - https://cyberdrain.com/automating-with-powershell-making-stolen-tokens-useless-with-global-secure-access/

* Huntress: vendor credential enables unauthorized access (the ConnectWise Cloud Backup incident) - https://www.huntress.com/blog/vendor-credential-enables-unauthorized-access

Multitenant apps and permissions:

* Application and service principal objects in Microsoft Entra ID (mentioned at 17:05) - https://learn.microsoft.com/en-us/entra/identity-platform/app-objects-and-service-principals

* allowedTenantsAudience (restrict a multitenant app to specific tenants, Graph beta) (mentioned at 17:18) - https://learn.microsoft.com/en-us/graph/api/resources/allowedtenantsaudience?view=graph-rest-beta

* How to configure app instance property lock (mentioned at 18:09) - https://learn.microsoft.com/en-us/entra/identity-platform/howto-configure-app-instance-property-locks

* Microsoft Graph permission types: delegated and application (mentioned at 18:48) - https://learn.microsoft.com/en-us/graph/permissions-overview

* Microsoft Graph permissions reference - https://learn.microsoft.com/en-us/graph/permissions-reference

* GDAP and the Secure Application Model (mentioned at 16:32) - https://learn.microsoft.com/en-us/partner-center/developer/gdap-and-secure-application-model

Credentials and rotation:

* Add and manage application credentials (mentioned at 21:00) - https://learn.microsoft.com/en-us/entra/identity-platform/how-to-add-credentials

* application: addKey (mentioned at 31:01) - https://learn.microsoft.com/en-us/graph/api/application-addkey?view=graph-rest-1.0

* Generate proof-of-possession tokens for rolling keys - https://learn.microsoft.com/en-us/graph/application-rollkey-prooftoken

* Configure app management policies (mentioned at 32:23) - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/configure-app-management-policies

* Managed identities and secretless authentication across tenants (mentioned at 28:21) - https://learn.microsoft.com/en-us/entra/identity/managed-identities-azure-resources/secretless-authentication

* Configure an app to trust a managed identity - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation-config-app-trust-managed-identity

Monitoring and response:

* Conditional Access for workload identities (mentioned at 27:38) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/workload-identity

* Disable user sign-in for an application (mentioned at 26:26) - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/disable-user-sign-in-portal

Tenants:

* Secure Future Initiative: eliminate identity lateral movement (mentioned at 34:32) - https://learn.microsoft.com/en-us/security/zero-trust/sfi/eliminate-identity-lateral-movement

* Microsoft actions following attack by nation state actor Midnight Blizzard (mentioned at 34:32) - https://www.microsoft.com/en-us/msrc/blog/2024/01/microsoft-actions-following-attack-by-nation-state-actor-midnight-blizzard

* Workforce and external tenant configurations (Microsoft Entra External ID) (mentioned at 37:17) - https://learn.microsoft.com/en-us/entra/external-id/tenant-configurations

Related Entra.Chat Episodes

* Stolen Tokens, Agents and Universal CAE: What Global Secure …

Most Conditional Access gaps aren’t exotic. They come from reading policies the wrong way: as firewall rules with an “allow”, as a list of platforms that seems complete, as an MFA exception for the office that made sense years ago. Brandon Colley has reviewed well over a thousand Conditional Access policies in customer assessments, and the same handful of mistakes come up in tenant after tenant.

Once those are fixed, the risk moves. Passkeys, privileged access and Conditional Access put more locks on the front door, the user sign-in. An app that was consented to years ago, holds a client secret and still has a stale redirect URI is a back door that none of those locks cover.

Brandon is a Senior Security Consultant at TrustedSec and a Microsoft Security MVP. He came from systems administration, learned Active Directory security at Trimarc, and now spends his days on cloud and on-premises assessments and the remediation that follows. These are the gaps he checks first, and the app and consent settings he has moved on to.

Security defaults can cover more admins than your policies

The free tier can be stricter than the paid one. Security defaults require MFA for 16 administrator roles. The Microsoft-managed policy “Multifactor authentication for admins accessing Microsoft Admin Portals”, and the “Require MFA for admins” template it mirrors, cover 14. The two extra roles in security defaults are Authentication Policy Administrator and Identity Governance Administrator.

If a small tenant is on security defaults, think hard before switching it off: the moment you do, you lose protections that you then have to rebuild in Conditional Access yourself.

Sponsored by:

ENow Software Introduces New Entra ID App Onboarding Experience

As user requests for SaaS and AI applications increase, Entra ID and M365 teams face a growing volume of security reviews, added hours of manual research, and bottlenecks.

New! ENow App Governance Accelerator 4.0 introduces App Onboarding, helping teams:

* Accelerate app approvals with configurable, multistage workflows.

* Evaluate security risks more efficiently with integrated Microsoft Defender for Cloud Apps risk scores.

* Reduce manual work with centralized requests, reviews, and approvals.

* Improve transparency with a self-service portal for requesters to track status and decisions.

* Control app sprawl with an Internal App Catalog of approved applications.

Go beyond Microsoft’s consent and approval capabilities with customizable, structured application governance, from the initial request through ongoing oversight.

Faster Approvals. Less Admin Work. Better Security Posture.

Learn More About ENow App Governance Accelerator 4.0

See It In Action: Request a Demo

Decide which roles are privileged yourself

“We require MFA on privileged roles” is easy to say in an audit. An assessment asks a harder question: privileged by whose definition? Brandon’s own list is about 36 roles, grouped into tier 0 and tier 1, the same tiering model Active Directory admins used 20 years ago.

Don’t lean on Microsoft’s mandatory MFA either. It covers the Azure portal, the Microsoft Entra admin center, the Intune admin center and the Microsoft 365 admin center, plus create, update and delete operations from Azure CLI, Azure PowerShell, the Azure mobile app and IaC tools. Microsoft Graph APIs are generally not in scope, so in some cases a single-factor sign-in can still reach Graph. Your Conditional Access still has to cover every app and every role you consider privileged.

Every platform is not all platforms

Conditions inside one policy combine with AND. A policy that requires MFA when the user is risky, the sign-in is risky and the location is outside the United States only fires when all three are true at once, so it almost never fires. Put conditions that should act on their own into separate policies.

The device platforms condition has the same trap. Ticking Android, iOS, Windows, macOS and Linux is not the same as “any device”. The platform comes from the user agent string, which isn’t verified and is easy to change, so a sign-in that claims an unknown platform matches none of your platform policies and walks past all of them. Microsoft’s recommended fix is a separate block policy: include Any device, exclude the platforms you support, and set the grant to Block access. Brandon covers how the spoofing works in his Petri article (linked below).

Watch this episode…

Conditional Access has no allow rule

Customers often ask for a policy that will “allow finance access to the finance app”. Conditional Access has no allow rule. A policy is an if-then statement: if the users, target resources and conditions match, then require MFA, a compliant device or another control, or block. Anything the policy doesn’t match passes through untouched.

So every time you narrow the users, the apps or the conditions to describe who should get in, you also shrink what the policy protects. Scope policies broadly and carve out exclusions on purpose.

Testing: ask what a policy doesn’t do

Testing usually covers the happy path: the right user opens the right app and gets an MFA prompt. The gaps are in the paths nobody tried: the user who isn’t in the group, the unmanaged device, the other network. Two locations, managed and unmanaged devices, a few apps and a few user types already make dozens of test cases, and every new condition (insider risk from Microsoft Purview, for example) multiplies them again.

The useful question isn’t “what does this policy do?” but “what doesn’t it do, and does something else cover that?” When you add a role or group to one policy, check whether it should come out of another.

Tools help:

* What If tool: simulate a sign-in for a user, app, device platform and location, and see which policies apply.

* Conditional Access Optimization Agent: Microsoft Security Copilot reviews your policies and suggests new policies (created in report-only mode) and changes for you to approve. It needs Microsoft Entra ID P1 and security compute units.

* AI with sanitized data: as a consultant, Brandon often can’t run tools inside a customer’s tenant. He exports the policies as JSON, removes tenant names, group names and IDs, and asks an AI model to explain a specific coverage question. Challenge the answers and verify them; don’t take them on trust.

User actions and device code flow

Two gaps Brandon still finds often:

* User actions. Conditional Access can target Register security information and Register or join devices. Without a policy on these, registering an MFA method or a device is protected only by whatever the sign-in itself required.

* Device code flow. Microsoft deploys a managed policy that blocks it in some tenants, but Brandon has seen it deployed only about three times. Check whether you need it: filter the sign-in logs by authentication protocol for device code and see who uses it. Legitimate users are usually input-constrained devices such as Teams phones and Teams Rooms. At one customer, the single device code sign-in turned out to be their own penetration test. Then block it with an authentication flows policy and exclude only what genuinely needs it.

Trusted locations: the exception that switches MFA off

A common policy reads: require strong authentication for all users, all apps, everywhere, except trusted locations. It was best practice once. In effect it means single-factor sign-in at the office, and it often survives after the rest of the policy has been modernized.

On Microsoft Entra joined and hybrid joined Windows devices you don’t need the exception for single sign-on. The primary refresh token (PRT) provides SSO to apps and carries the MFA claim. The exception only lets users skip strong authentication.

Flip how you use locations. Instead of using them to relax MFA, use them to lock down the accounts that can’t do MFA, such as service accounts, shared accounts and kiosk accounts, so they only work from specific IP ranges and devices.

While you’re there:

* MFA trusted IPs in the legacy MFA service settings ar…

Most tenants have the same problem: hundreds of app registrations and service principals, client secrets that were set to expire in a hundred years, permission grants nobody remembers approving, and test tenants that were never cleaned up. It’s tempting to start fixing the scariest app on the list. Jeff Sakowicz argues for a different order: stop the problem from growing first, then remove the debt that gives you the most risk reduction for the least disruption.

Jeff isn’t describing someone else’s product. He has spent most of his 14 years at Microsoft as a product leader on the Entra application platform, shaping the application and service principal model and the OAuth permissions and consent model that every Entra tenant runs on today. Publisher verification and risk-based step-up consent came out of that work, and he now leads part of the team building the platform behind Microsoft Entra Agent ID. Inside Microsoft, he’s the person teams call when an app incident needs untangling. This is his playbook for securing non-human identities, from client secret burndown and unused apps to consent phishing and the protections Microsoft runs in every tenant by default.

Prevention starts with policy

The best medicine is prevention. Before you clean anything up, go through the policy controls you already have and set them to block insecure configuration that doesn’t fit your organization’s risk tolerance. This is a balance, not a switch. “If you want the most secure system in the world, unplug the server, bury it underground. Your job is done.” Lock things down too hard and developers and end users will find other ways to get work done, especially now that they have agents to help them. Shadow IT is almost always less secure than what you stopped. So whenever a control blocks self-service, make sure people know what to do next and how to get unblocked quickly.

Treat high-value apps as production infrastructure

Microsoft runs customer-facing apps in tenants separate from its corporate tenant. Tenant-level isolation is a useful form of segmentation, and some large organizations do the same for their production assets. But a second tenant brings its own operational overhead, and a tenant that falls into chaos can leave you worse off than before.

Whatever you decide, treat your multitenant apps and high-value line-of-business apps as production infrastructure, the same way you would protect a database or a high-value Azure subscription. A good middle ground is to keep a close eye on the owners and sponsors of your high-value apps and agent identities. They are the people who can change those identities’ authentication configuration, so their accounts need good hygiene.

The easier win is test, demo and staging. If they still live in your productivity or production tenant, move them out. Midnight Blizzard showed how small dominoes lead to big consequences: Microsoft’s own write-up describes a password spray against a legacy, non-production test tenant account, followed by a legacy test OAuth application that had elevated access to the corporate environment.

Sponsored by

Many of the app and consent problems in this episode are exactly what Maester checks for: it runs security tests against your Microsoft Entra and Microsoft 365 configuration and tells you what passed and what failed.

Maester Cloud turns those results into a workflow your team can run every day:

* Assign an owner to each finding and link it to a ticket, instead of tracking remediation in a spreadsheet.

* See what got fixed since the last run, and record accepted risks.

* Catch drift with daily history and alerts when a setting changes.

* Every tenant in one place, without switching sign-ins.

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Map your surface area, then think in three dimensions

Before buying a new inventory tool, use the one you already have. If your organization already tracks production assets or other identities, bring your non-human identities into that system instead of running a parallel process. Then answer three questions: how many of these do I have, what categories of identity are in the portfolio, and what are the big categories of risk?

Jeff looks at risk in three dimensions:

* Active threats. Priority zero. Hand them to the SOC immediately.

* Posture. Surface area from misconfiguration, or configuration that was state of the art five years ago, such as the implicit flow for a single-page app. Weak credentials, insecure redirect URIs, unused identities and legacy protocols all live here.

* Blast radius. How much privilege each identity has, whether it’s used or not.

Most organizations end up with a huge list of high-privilege apps and posture issues. You will never get every risk to zero at that scale, so the job is to prioritise by risk and by return on effort.

Burn down secrets: stop the bleeding first

Say you’ve read the Solorigate reports and want to get client secrets off your non-human identities. Step one is to stop the bleeding: create an app management policy that blocks new password credentials from being added. App management policies can take an enforcement date, so only apps created after that date are affected and your hundreds of existing apps keep working while you fix them. There is no equivalent for user authentication methods.

Before you switch it on, find out how disruptive it will be. One new app a month that uses a password credential is easy to absorb. A hundred a day could grind the organization to a halt. Have the guidance and the exception process ready, and move the enforcement date if you need to.

Once the problem has stopped growing, turn to the debt. Split it into categories and start with the two ends of the spectrum:

* The most privileged. Apps with existing passwords that have app-only access to read all mailboxes or read and write all user profiles go to the top of the list. Move them to a stronger credential and check whether they need that access at all.

* The wholly unused. More on this below.

The end goal is system-managed credentials, using a managed identity or workload identity federation with a federated identity credential (FIC). You can argue a certificate’s private key is harder to leak than a secret, but as Jeff says, “a bad copy-paste is a bad copy-paste.” System-managed credentials also remove a big source of toil for developers, which helps when you need people to move.

Why mail is the flag

Mail permissions can look less frightening than broad directory permissions, but for many attacks mail is the goal. “Mail’s often the flag that the attacker’s trying to capture.” Other access is often just a way to move laterally or elevate privilege. Mail, Teams chats and files can be the end goal, and that is what most historical consent phishing attacks went after. A mailbox is also a good lateral movement tool: it can hold credentials and bank details, and it gives an attacker what they need to craft a convincing social engineering attack against everyone the victim emails or chats with every day.

Lost secrets make this worse. A secret that is valid for years, used by apps nobody can name, gives an attacker a way in without adding a new credential, so there’s no new event for you to trace.

Unused identities: the highest return on effort

A wholly unused identity is the highest-ROI bucket. “If you get rid of an unused identity, you might be knocking an item off of seven lists.” In one move you can remove a weak password, an insecure redirect URI, overprivileged access and some legacy protocol usage. Do your due diligence first, because some apps only run once a year at tax season. But removing something that is truly unused doesn’t disrupt anyone, and it can be done as a central action by a single team without engaging every app owner. That high-leverage central action is what Microsoft leaned into for its Secure Future Initiative work.

Then look at low-usage identities. They hide in plain sight: an identity with an automated runner that wakes up every day to run a test…

A phished and stolen refresh token is one of the most useful things an attacker can take from your tenant. It is a long-term artifact, which is why so many phishing attempts go after it. Alex Pavlovsky’s answer to that attack is a feature every Entra ID P1 tenant already owns.

Compliant network is part of Global Secure Access, and, like source IP restoration, it comes with Entra ID P1. Put the GSA client on your devices, add one Conditional Access policy that blocks access from anywhere outside the All Compliant Network locations named location, and a stolen refresh token or PRT cookie no longer works from the attacker’s own machine. As Alex puts it, the token itself does not become bound, but your use of it is gated by being on your organization’s compliant network.

Merill is joined by two former colleagues who are Microsoft Entra PMs: Alexander (Alex) Pavlovsky from the Global Secure Access feature team, and Marilee Turscak, who works on helping customers adopt AI safely. They explain why Microsoft built networking into identity, walk through the compliant network policy and a BYOD sign-in with no client installed, and demo a network policy that stops an agent from deleting a file its user is allowed to delete.

Why a stolen token stops working

For phishing itself, Alex is clear that the main line of defence is still stronger credentials that do not involve passwords. Compliant network helps with what comes after: the newer attack patterns where refresh tokens are stolen and replayed.

If your tenant-wide policy says you can only authenticate from a compliant network, you can also only replay refresh tokens from a compliant network. PRTs become unusable unless they are used from a device that has GSA, which means your organization’s device. Alex says the same applies to ROADtools-style attacks with PRT cookies: none of that works with compliant network in place. The signal is also tenant-specific. A GSA device in tenant B satisfies compliant network in tenant B and nowhere else.

In the demo, Alex builds the policy in a few clicks: all users, all resources (so the primary refresh token, Entra ID itself and Microsoft Graph are covered), any network except compliant network locations, then block. Start it in report-only mode, watch who is not coming through compliant network, pilot with a smaller group and expand. You do not need the advanced GSA licences for this, but you do need the GSA client on your devices or a remote network sending the traffic.

And exclude your break glass accounts. Alex has taken many panicked customer calls from admins who forgot, and Marilee locked herself out of a test tenant this way recently.

One engine for identity and network

When Merill joined Microsoft, he couldn’t see why networking belonged to the identity team. Alex explains the reasoning. When identity picks up a signal that a user, session or token is at risk, the network has to hear about it quickly, and passing those signals between separate systems through traditional APIs is too slow at this scale. So Microsoft made the identity engine and the network engine one engine.

That design shows up in source IP restoration. Behind a typical proxy or security service edge, every user looks like they signed in from the provider’s shared IP range. GSA sends the user’s original source IP to Entra securely, so sign-in logs are accurate, Conditional Access can evaluate the user’s own IP, and Identity Protection’s location and impossible travel detections work again. It is also why compliant network works at all: the GSA edge shares a security engine with Entra ID, so it can tell Entra that this is a legitimate GSA device from a specific tenant, and Entra can trust that signal.

The network can tell agents from users

“Agents are super deterministic. They are very resourceful. They do not give up.” Alex also argues that saying no to agents means falling behind your competitors, so the question becomes how to protect their use.

GSA can detect when network access comes from an agent, and its policy rules can match on the HTTP method, the destination and whether a user or an agent is acting. Marilee’s baseline recommendation is to block sensitive actions by agents. In her demo, the Zava helper agent tries to remove a document from Dropbox and gets an “agent is not authorized” error, because a policy called “block agents from destructive actions” blocks the DELETE method for agents only. The user checkbox is left clear, so the person can still delete the file themselves. The logs show the same attribution, which Alex says is valuable even before you apply any policy.

Alex also describes Copilot Studio agents running through GSA with no client anywhere. A Copilot Studio admin checks one box to enable the GSA integration, and with Internet Access and a policy in place, that agent traffic flows through GSA and your policies apply.

BYOD without the client

Marilee shows a user on a personal device with no GSA client. When she signs in, she is prompted to switch to her work browser profile, and from then on Explicit Forward Proxy sends that profile’s traffic through GSA. When she tries to open Facebook, she is blocked inside the work profile and nowhere else on her device. Alex sees the managed Edge profile becoming a sandbox with secure network access and Purview DLP, which could reduce the need for remote browser isolation. The full client still gets the most features, including agent detection, and remote networks are a third way to send traffic through GSA.

Universal CAE now acts on device state

Continuous access evaluation used to depend on applications that understood it, which mostly meant SharePoint, Teams and Exchange. Send an app’s traffic through GSA and it becomes CAE-aware too, including private apps. If an admin is on an SSH session over GSA and Entra flags their identity, Alex says the session is dead within about two to five minutes, even if their token is good for another 90 minutes.

The week before recording, Microsoft added device state support. If Intune or a third-party MDM marks a device non-compliant in Entra ID, GSA asks the user to bring it back into compliance or lose network connectivity. User risk changes and device deletion or disablement also trigger it now. If you already run GSA, you get this without changing anything, which is Merill’s favourite kind of feature.

If you have Entra ID P1 and have never deployed the GSA client, compliant network is the place to start.

About Alexander Pavlovsky

Alexander Pavlovsky is a Product Manager on the Microsoft Entra Global Secure Access feature team. He has been at Microsoft for 22 years. He started in Microsoft Consulting, installing domain controllers and Exchange servers for customers from CDs, then moved to the identity product team as a customer-facing PM in the Entra GTP (Get To Production) team, later CXE (Customer Experience), helping organizations adopt Azure AD.

LinkedIn - https://linkedin.com/in/alexpav

About Marilee Turscak

Marilee Turscak is a Product Manager on the Microsoft Security team focusing on Microsoft Entra. For the past two years she has focused on getting customers deployed across the Microsoft Entra Suite, and she now works on helping customers adopt AI safely and securely.

LinkedIn - https://linkedin.com/in/marilee-turscak

Related Links

* What is Global Secure Access? - overview and the licensing table for each feature (mentioned at 10:08) - https://learn.microsoft.com/en-us/entra/global-secure-access/overview-what-is-global-secure-access

* Source IP restoration (mentioned at 15:07) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-source-ip-restoration

* Universal Conditional Access (mentioned at 15:26) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-universal-conditional-access

* Universal Tenant Restrictions (mentioned at 15:26) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-universal-tenant-restrictions

* Compliant network check with Conditional Access (mention…

Ask a coding agent to build something that talks to another service and watch what it does. It creates a client secret. Then another one. As Arturo Lucatero puts it, next thing you know you have ten secrets that were created without you knowing about it. At the speed AI is moving, he thinks we could be cleaning up a few million new secrets within six months.

That would undo a lot of hard work. Under Microsoft’s Secure Future Initiative, Microsoft spent years removing secrets from its own estate and helping customers do the same with managed identities and workload identity federation. The agent era is the window to make secretless the default before the habit sets in.

Arturo is a Principal Product Manager on Microsoft Entra Agent ID, and he helped launch Managed Service Identity, the feature we now call Managed Identities for Azure resources. In this episode he and Merill trace the whole path: why secrets break, how managed identity takes them away inside Azure, how workload identity federation extends that to AWS, GCP, Azure Arc and now AI vendors like Anthropic, and what that means for agents.

Secrets work until they don’t

A service principal with a client secret works. It works right up to the moment it gets leaked, expires in the middle of an important job, or turns out to have no clear owner, no rotation plan and no one who knows where it is stored. Managed identity moves that whole burden to the platform. The secret still exists, but the developer never sees it. The admin’s job shrinks to control-plane questions: which resource, which identity, and what it can access. Arturo also hints at what comes next: binding managed identity tokens to the resource so a leaked token is useless anywhere else.

Beyond Azure

Not every workload or data source lives in Azure. Workload identity federation lets a workload present a token from an identity provider you already trust, such as AWS, Google Cloud, GitHub or Kubernetes, and exchange it for an Entra token with no secret involved. Azure Arc brings managed identity to servers outside Azure, including the one under your desk, which raised a hard design question for the team: what happens to the secret when the machine is in someone’s basement?

Coding agents default to secrets

Coding agents learned from years of examples full of client secrets and Key Vault plumbing, so that is what they produce. Merill has to push his own agents back towards workload identity federation every time. Arturo hit the same problem from the inside: when he asked a coding agent to build with Agent ID, it created a plain service principal and named it “blueprint”. The fix was rewriting documentation and shipping agent skills that teach coding agents the right pattern.

Why agent identities still allow client secrets

Merill asks the obvious question. If secrets are this bad, why can an agent identity have one? Arturo’s answer is compatibility. Agent identities already authenticate through a federated identity credential flow under the hood, but many places that call agents cannot obtain an OIDC token yet. Without secrets or certificates as a fallback, people would simply keep using app registrations.

Open standards are the way out

Agents now cross identity providers and clouds every day. Entra is leaning on open standards so they can do that without secrets or interrupting users: SPIFFE identities that can be exchanged for Entra tokens, and ID-JAG, which lets admins pre-consent so an agent can reach a service like GitHub or Slack without prompting the user.

Arturo’s advice for anyone building today is simple: whatever you can do to avoid having a secret, do it.

Is Each App in Entra ID Still Worth Governing?

App registrations and enterprise applications accumulate. Owners change. Projects and pilots end. Credentials linger. And stale or unused apps and their permissions can continue adding risk and governance overhead long after their purpose is gone.

ENow App Governance Accelerator helps you understand and act on:

* What is in your Entra ID application estate

* Who owns business and technical decisions and management?

* Which apps, permissions, and credentials need attention?

* What can be safely cleaned up to reduce your attack surface on a continuous basis as your tenant grows and changes?

Get the visibility and automated workflows you need to investigate application lifecycles at scale, clear out stale apps, and stop wasting time governing applications that shouldn’t still be there in the first place.

See it in Action

Subscribe with your favorite podcast player or watch on YouTube

About Arturo Lucatero

Arturo Lucatero is a Principal Product Manager at Microsoft working on Microsoft Entra Agent ID, where he focuses on giving agents a strong, governable identity and on the developer experience for building with it, including skills that teach coding agents to use Agent ID correctly. He joined Microsoft’s identity team after a re-org moved him there from Power BI, worked on Connect Health, and then helped Stuart Kwan launch Managed Service Identity, now managed identities for Azure resources. Most of his career has been spent modernising non-human identities, from managed identity and Azure Arc to workload identity federation.

LinkedIn - https://www.linkedin.com/in/arturo-lucatero/

Related Links

* Microsoft Entra Agent ID skill for coding agents, in GitHub Copilot for Azure (mentioned at 32:52) - https://github.com/microsoft/GitHub-Copilot-for-Azure/blob/main/plugins/azure-skills/skills/entra-agent-id/SKILL.md

* AI-guided setup for Microsoft Entra Agent ID, using the skill with GitHub Copilot (mentioned at 32:52) - https://learn.microsoft.com/en-us/entra/agent-id/agent-id-ai-guided-setup

* Ben Reader: Access Azure Key Vault from a local Kubernetes cluster with Azure Arc workload identity (mentioned at 22:32) - https://powers-hell.com/2026/08/26/access-azure-key-vault-from-a-local-kubernetes-cluster-with-azure-arc-workload-identity

* Ben Reader: Run a PowerShell workload on a local Kubernetes cluster that talks to Microsoft Graph (mentioned at 22:32) - https://powers-hell.com/2026/09/08/run-a-powershell-workload-on-a-local-kubernetes-cluster-that-talks-to-microsoft-graph

* Managed identities for Azure resources, formerly Managed Service Identity (mentioned at 04:50) - https://learn.microsoft.com/en-us/entra/identity/managed-identities-azure-resources/overview

* Workload identity federation (mentioned at 15:18) - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation

* Workload Identity Federation for the Claude API (mentioned at 16:27) - https://platform.claude.com/docs/en/manage-claude/workload-identity-federation

* Agent identity blueprints in Microsoft Entra Agent ID (mentioned at 20:35) - https://learn.microsoft.com/en-us/entra/agent-id/agent-blueprint

* Access Azure resources with managed identity on Azure Arc-enabled servers (mentioned at 23:09) - https://learn.microsoft.com/en-us/azure/azure-arc/servers/managed-identity-authentication

* SPIFFE and SPIRE (mentioned at 27:41) - https://spiffe.io/

* Federate a SPIFFE/SPIRE workload identity with Microsoft Entra ID (mentioned at 29:25) - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation-spiffe-spire

* Pieter Kasselman: SPIFFE at the BotAuth BoF, IETF 123 (mentioned at 29:53) - https://datatracker.ietf.org/meeting/123/materials/slides-123-webbotauth-spiffe-at-the-botauth-bof-pieter-kasselman-00

* Identity Assertion JWT Authorization Grant (ID-JAG), IETF draft (mentioned at 30:21) - https://datatracker.ietf.org/doc/draft-ietf-oauth-identity-assertion-authz-grant/

* Microsoft Secure Future Initiative (mentioned at 06:30) - https://www.microsoft.com/en-us/trust-center/security/secure-future-initiative

Related Entra.Chat Episodes

* One Compromised Agent ID Blueprint Can Cross Tenant Boundaries - https://entra.news/p/one-compromised-agent-id-blueprint

* From Windows Core to Leading Agent ID: Vince Smith’s Microsoft Story - https://entra.news/p/from-windows-core-to-leading-agent

* Attackers Are Targeting the AI Ecosy…

Active Directory is not dead. It is nearly thirty years old, Microsoft is still shipping new capabilities and new telemetry for it, and most of the forests running today will outlive the people currently administering them. What has changed is that you can now test it the same way you test your cloud tenant.

Maester, the open-source PowerShell testing framework, added Active Directory coverage: 269 opt-in checks across 19 areas, from users, groups, computers and service principal names through GPO state, DACLs, DNS, trusts, replication and schema. They run against your domain, not your tenant, and they are off unless you explicitly connect to Active Directory.

Mike Soule, who wrote and validated that test suite, and Sam Erde, Microsoft MVP and author of DLLPickle, join Merill at HIP Conf in Nashville to go through what the tests cover, how to run them safely, and where the project is heading.

Sponsored by:

Is Each App in Entra ID Still Worth Governing?

App registrations and enterprise applications accumulate. Owners change. Projects and pilots end. Credentials linger. And stale or unused apps and their permissions can continue adding risk and governance overhead long after their purpose is gone.

ENow App Governance Accelerator helps you understand what’s in your Entra ID application estate, who owns it, which apps, permissions, and credentials need attention, and what can safely be cleaned up to reduce your attack surface on a continuous basis as your tenant grows and changes.

Get the visibility and automated workflows you need to investigate application lifecycles at scale, clear out stale apps, and stop wasting time governing applications that shouldn’t still be there in the first place.

Operational health is not the same as a security finding

The design decision that makes these tests usable is the split between operational patterns and security controls. Six groups nested in a row is not a vulnerability. Nesting is an intentional, functional capability. It is also nearly impossible to reason about when you are trying to work out where a permission actually comes from, and that is how incidents happen.

So not every test is pass/fail. Some exist to be investigated and monitored, and Maester’s tagging lets you baseline them and watch whether an anti-pattern is spreading or receding over time. The underlying guidance is a blend: years of health checks across dozens of forests, community research from teams like Semperis and SpecterOps, and Microsoft’s own documentation — which, for a product people keep declaring dead, is currently some of the best documentation and logging Microsoft ships. The new NTLM auditing in Windows Server is the example: the who, the why and the where of every NTLM authentication, instead of replaying events and correlating them yourself.

Maester is not trying to replace the likes of PingCastle, Purple Knight or Locksmith. Those tools offer real value, and the conversation now is about bringing those perspectives into one central platform.

The permissions you actually need

Everything the AD tests do is read-only. A plain domain user gets a surprising amount, because a directory is built to be readable — you will simply get a subset of the tests. The full set needs tier-zero read access, because some tests reach objects in the configuration container. In a tiered environment, that means running as a tier-zero admin from a privileged admin workstation.

Interactively, there is nothing to set up beyond line of sight to a domain controller, the ActiveDirectory module and PowerShell. The AD tests are excluded by default and have to be requested by tag. For automation, run a local runner, or give a container runtime a path back to a domain controller. Today the tests run as the logged-in user’s domain credentials; alternate credentials and group managed service accounts are on the road map.

Tiering, ESAE and the enterprise access model

There are no explicit tiering tests yet, but they are coming now that Microsoft has published implementation guidance. The history is worth knowing. ESAE — the Enhanced Security Admin Environment, the red forest — solved a real problem: inside Active Directory, a domain admin is trusted implicitly, so the source of authority needs to sit somewhere that is not self-referential. A separate management forest achieves that, at a cost in operational complexity that most organisations could not sustain. Microsoft has since moved to the enterprise access model, and in practice most teams landed in the middle: tiering based on access control, with tier zero for core identity infrastructure, tier one for servers, databases and applications, and tier two for workstations and the workforce.

The advice is not all-or-nothing. Any amount of effort you put into tiering is a good investment. Where Maester helps is codifying Microsoft’s recommended implementation as tests you can actually check yourself against, including the DACL and inheritance anti-patterns that accumulate through ordinary operations.

What is coming next

The dependency on the ActiveDirectory PowerShell module is on its way out. Almost all of this work is LDAP-level, so a .NET-based approach covers the vast majority of tests with no module dependency — which opens up Linux, macOS and non-domain-joined machines. Multi-domain aggregation is in progress; today a run covers a single domain at a time. And Maester 3 is being planned around a new engine for the built-in tests, with multi-threading and parallel execution, licensing handled centrally instead of inside every test, and Pester retained for backward compatibility and custom tests.

Subscribe with your favorite podcast player or watch on YouTube

About Michael Soule

Mike Soule is a Maester co-maintainer and National Director of Enterprise Architecture at Sentinel Technologies, where he works with enterprise customers on identity, cloud and security. He wrote and validated the Active Directory test suite that shipped in Maester 2.2 — 269 opt-in checks across 19 areas — and has been the project’s leading test contributor since the night after Maester’s launch talk at the PowerShell Conference, when he turned up the next morning with roughly thirty CISA tests already written.

LinkedIn - https://www.linkedin.com/in/mikesoule/

GitHub - https://github.com/soulemike

About Sam Erde

Sam Erde is a Maester co-maintainer and a Microsoft MVP, working at Patriot Consulting. He has spent more than twenty years in PowerShell, Active Directory, Group Policy, Exchange and Microsoft 365, contributes to open-source defensive tooling including Locksmith, and wrote DLLPickle, the module that gets you out of assembly version conflicts when several Microsoft modules are loaded in one session.

LinkedIn - https://www.linkedin.com/in/samerde/

GitHub - https://github.com/SamErde

Related Links

* Maester - open-source PowerShell test automation for Microsoft 365, Entra and now Active Directory (mentioned at 00:21) - https://maester.dev

* Introducing Maester 2.2 - the release that added 269 opt-in Active Directory checks across 19 areas (mentioned at 04:50) - https://maester.dev/blog/maester-2-2/

* Active Directory security testing in Maester - what the tests cover and how to run them (mentioned at 04:50) - https://maester.dev/blog/active-directory-security-testing/

* Maester on GitHub - source, tests and contribution guide (mentioned at 03:44) - https://github.com/maester365/maester

* Locksmith - Jake Hildreth’s AD CS assessment and remediation tool (mentioned at 05:11) - https://github.com/jakehildreth/Locksmith

* NTLM auditing enhancements in Windows 11 24H2 and Windows Server 2025 (mentioned at 09:53) - https://support.microsoft.com/en-us/topic/overview-of-ntlm-auditing-enhancements-in-windows-11-version-24h2-and-windows-server-2025-b7ead732-6fc5-46a3-a943-27a4571d9e7b

* AD DS tier model for privileged access security (mentioned at 24:47) - https://learn.microsoft.com/en-us/windows-server/identity/ad-ds/tier-model

* Securing privileged access - the enterprise access model …

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 Securit…

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.

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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 Migrat…

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.

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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/ide…