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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 are IPv4-only and not recommended. The “All trusted networks and locations” option in Conditional Access includes them. The checkbox to skip MFA for federated users on your intranet belongs to the same legacy settings. * Continuous access evaluation checks IP-based named locations at the resource. Include both IPv4 and IPv6 ranges, or IP mismatches will cause unexpected behaviour. * Check your ranges. Few admins still calculate subnets by hand. AI can help, as long as you check the answer: ask whether a specific IP is inside a specific range rather than accepting “it’s a /8”. * Compliant network. With Global Secure Access and the Microsoft traffic profile, the compliant network check in Conditional Access is included with Microsoft Entra ID P1. It follows the device rather than the building, which suits people who move around with their laptops. Apps: the back door There are no unpatched Entra servers for an attacker to exploit, so the ways in are user sign-in and apps. Once an app is in the tenant, consented, holding permissions and a client secret, it lives there until someone actively looks at it. A single leaked client secret can be all an attacker needs, and none of the controls on user sign-in apply to it. Prefer certificates, and better still managed identities or workload identity federation, over client secrets. Redirect URIs and dangling domains A redirect URI (reply URL) is where Microsoft Entra sends the token after a user signs in. If an attacker controls that URL, they get the token from a completely legitimate Microsoft sign-in, usually started by a phishing link. Watch for three kinds: * Old redirect URIs left behind after an app moved. * Wildcards, which Microsoft’s guidance says not to use. * Reclaimed domains: names you let go that someone else can register. The classic case is azurewebsites.net. Deve

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. Subscribe with your favorite podcast player or watch on YouTube 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 suite won’t show up as unused, and may not be privileged enough to make your red list. Look closely and you find the same two token requests every day for months, with no person or agent relying on them. Microsoft Entra recommendations already flag unused applications and unused credentials. Consent phishing and your consent policy A small set of controls drastically reduces the chance of a compromise through consent phishing, and the first is a consent policy. Microsoft has revised the defaults several times over the last few years and they are now in a good state, but check yours and tune it for your organization. Older tenants deserve a second look in both directions. Many organizations turned user consent fully off around 2019, when consent phishing surged and the setting was just on or off. The modern consent policy framework now offers far more granular options, so you can enable the self-service your business needs without opening a hole. Note that changing your consent settings only affects future consent; existing grants stay in place. The protections you don’t see Publisher verification is more than a blue checkmark. Microsoft uses it as a signal in several places. By default, multitenant apps registered after November 8, 2020 that don’t have a verified publisher can’t get user consent from other tenants unless they only ask for basic sign-in and profile permissions. Risk-based step-up consent is another. It’s on by default in every tenant, and when a user consent request looks risky it requires an admin instead, even when the user would normally be allowed to consent. Microsoft built it this way because once a user takes the lure and lands on a consent screen, “the click-through rate on the actual consent prompt was very, very high.” The best defence is to stop them getting there. Microsoft also detects and takes down campaigns that use m

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 (mentioned at 18:24) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-compliant-network * ROADtools - the Azure AD and Entra ID exploration framework behind many PRT cookie attacks (mentioned at 21:19) - https://github.com/dirkjanm/ROADtools * BYOD with Global Secure Access (mentioned at 23:30) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-bring-your-own-device * Explicit Forward Proxy overview (mentioned at 24:31) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-explicit-forward-proxy * Configure Explicit Forward Proxy for Microsoft Edge with Intune (mentioned at 25:06) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-configure-explicit-forward-proxy-intune-policy * WebMCP (mentioned at 27:05) - https://github.com/webmachinelearning/webmcp * Remote network connectivity (mentioned at 27:54) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-remote-network-connectivity * Web filtering, including rules that match on user or agent and HTTP method (mentioned at 29:43) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-web-filtering * AI agent discovery (mentioned at 29:43) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-ai-agent-discovery * Secure Web and AI Gateway for Copilot Studio agents (mentioned at 34:13) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-secure-web-ai-gateway-agents * Set up Global Secure Access for Copilot Studio agents (mentioned at 34:13) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-secure-web-ai-gateway-agents * Tutorial: require a compliant network for Microsoft traffic (mentioned at 39:22) - https://learn.microsoft.com/en-us/entra/global-secure-access/tutorial-microsoft-traffic-compliant-network * Manage emergency access (break glass) accounts (mentioned at 41:01) - https:

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 Ecosystem You Cannot See - https://entra.news/p/attackers-are-targeting-the-ai-ecosystem Chapters 00:00 Intro01:19 Arturo’s path from Intel to identity04:50 Launching Managed Service Identity07:06 Why MSI became managed identities09:41 How managed identity removes the secret14:31 Beyond Azure: workload identity federation17:08 Coding agents and the new secret sprawl20:01 When a coding agent fakes an Agent ID blueprint22:32 Managed identity anywhere with Azure Arc24:42 Why agent identities still allow client secrets27:41 Open standards: SPIFFE and ID-JAG31:48 What developers should do today 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

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 that replaced ESAE (mentioned at 25:23) - https://learn.microsoft.com/en-us/security/privileged-access-workstations/privileged-access-access-model * DLLPickle - Sam Erde’s module for PowerShell assembly version conflicts (mentioned at 16:16) - https://github.com/SamErde/DLLPickle * HIP Conference - Hybrid Identity Protection, Nashville, where this episode was recorded (mentioned at 01:18) - https://www.hipconf.com/ * PowerShell DSC (mentioned at 31:34) - https://learn.microsoft.com/en-us/powershell/dsc/overview Chapters 00:00 Intro 00:40 Is Active Directory dead? 01:41 How Maester started and Mike’s overnight tests 04:50 Active Directory tests in Maester 2.x 05:03 How Maester compares to PingCastle and Locksmith 07:03 Operational health checks vs security findings 08:43 Where the AD guidance comes from 11:12 Running the tests and the permissions you need 13:53 Dropping the ActiveDirectory PowerShell module 15:18 One report for AD and cloud plus a Maester 3 teaser 17:20 Performance and memory in very large forests 20:23 Never run it on a domain controller 23:03 Multi-domain and multi-forest scans 24:14 Testing AD tiering and the enterprise access model 28:02 Beyond AD: DNS and Windows Server roles 28:50 Validating GPOs and desktop builds with Maester 31:25 Maester vs DSC and config-as-code 35:49 AD is not dead 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.Ne

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_VV

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 wr

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

An Entra GSA migration should not mean throwing away years of useful SSE policy work and rebuilding every application, segment, and rule by hand. Existing configuration carries hard-won intent: which populations need access, which destinations should be blocked, and which exceptions keep the business running. Migrate2GSA creates a path to preserve the useful parts while making the migration a deliberate cleanup opportunity. In this episode of Entra.Chat, I spoke with Andres Canello, Principal Product Manager at Microsoft and creator of Migrate2GSA. Andres demonstrates how the open-source toolkit exports configuration from third-party products, converts it into a common CSV schema, gives administrators an intentional review step, and provisions the approved configuration into Global Secure Access through Microsoft Graph. The goal is not to configure the product end to end or remove human judgment. Andres describes it as a way to accelerate the repetitive 80%. Conflicting segments default to “do not provision,” existing applications are skipped, generated Conditional Access policies remain disabled, and there is no delete API call in the toolkit. The conversation also covers greenfield provisioning, backup and restore, reusable consultant baselines, and the unusual development story behind more than 30,000 lines of PowerShell. Andres explains why detailed, published specifications produced better AI-generated code than incremental prompting—and why the intent and edge cases in an open-source contribution matter more than who typed the implementation. Subscribe with your favorite podcast player or watch on YouTube. About Andres Canello Andres Canello is a Principal Product Manager at Microsoft, where he works at the intersection of modern identity and Secure Service Edge. Over his 15 years at Microsoft, he was a founding member of the Entra Global Secure Access team, helping shape the product before it launched, and has since guided some of the largest identity and secure-access deployments in the industry, from banks and miners to national governments. He’s the creator of Migrate2GSA, an open-source migration toolkit used by organizations around the world, which he built end-to-end using AI-assisted, spec-driven development. * Andres Canello on LinkedIn * Andres Canello on X/Twitter Sponsored by Maester Cloud turns every Maester and Microsoft Zero Trust Assessment run into a durable evidence trail. See new failures, fixes, accepted risks, and posture changes across every tenant - without digging through old HTML reports. * Keep 5+ years of tenant history in your chosen Azure region * Compare runs, spot drift, and get change alerts Become a Founding Supporter for $99/month to fund open-source Maester development, shape the roadmap, and get self-hosted private-preview access plus 10% off hosted for life. Related Links * Plan and troubleshoot UserPrincipalName changes in Microsoft Entra ID (mentioned at 04:07) * Azure AD Mailbag: Conditional Access Q&A by Andres Canello (mentioned at 06:43) * Migrate2GSA documentation (mentioned at 45:37) * Migrate2GSA source repository (mentioned at 45:37) Related Entra.Chat Episodes * How to Migrate from Legacy VPNs to Entra Private Access (Real Strategies from a Veteran) * Global Secure Access Explained: Real-World Rollouts, Mistakes, and Best Practices * Identity-Centric Network Security: Entra Global Secure Access Architecture & Benefits Chapters 00:00 Intro 01:05 Andres Canello's 15 Years in Microsoft Identity 06:43 A Conditional Access Mistake Admins Still Make 11:29 From Early Customer Pilots to Entra GSA 13:21 Why SSE Migrations Should Not Start From Scratch 18:31 Beyond Migration: Backup Restore and Greenfield 23:27 Export Convert Review and Provision 27:02 How Specifications Made AI-Generated PowerShell Work 35:22 Conflict Detection and the Human Review Gate 39:14 Microsoft Graph Provisioning with Safety Built In 43:35 Automating the Repetitive 80 Percent 46:15 Contributing to Migrate2GSA Podcast Apps * Entra.Chat * Apple Podcast * YouTube * Spotify * Overcast * Pocketcast * Other podcast apps Merill’s socials * YouTube * LinkedIn * Twitter * TikTok * Bluesky * Mastodon * Threads * GitHub Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe

Conditional Access no longer begins and ends with identity signals. Microsoft Purview can now influence the controls Entra administrators are asked to implement. From insider-risk conditions in Conditional Access to inline protection for sensitive data moving toward unsanctioned AI apps. That means Entra teams need enough Purview knowledge to understand what triggers a policy, how users experience it, and who should respond when an alert fires. In this episode of Entra.Chat, Merill speaks with Ray Reyes, Principal Security Consultant at Engage Squared and author of Mastering Microsoft Purview Deployment in the Era of AI. Ray explains Data Loss Prevention and Insider Risk Management in plain language, then follows their integrations into Microsoft Entra ID, Microsoft Defender XDR, and Global Secure Access. The conversation moves beyond product configuration. A policy can be technically simple and still require identity, network, data-security, HR, management, and data-owner teams to agree on scope, ownership, education, escalation, and remediation. Ray’s practical advice is to understand the neighbouring Microsoft security products at a high level and deploy Purview gradually: start in audit mode or with a limited group, learn from the impact, and expand with the business. Ray also shares the story of the charity he and his wife started in Nepal, how it grew from supporting roughly 30 street children to reaching thousands, and how that chapter changed his perspective on work and stress. He and Merill close with an honest discussion about burnout, layoffs, gratitude, personal branding, and building a career safety net outside any one employer. Sponsored by Recent layoffs have left a lot of strong professionals in limbo. That’s why we built Sponsor a Seeker, a simple way for the community to lift each other up. For just $29, you can gift a full 3-month Job-Hunt Pass packed with: • Unlimited resume & job description scans • AI-powered rewrites that actually beat ATS systems • Professional cover letter generation Every dollar goes directly to the seeker. You can: → Sponsor someone like Alex M. (recently laid off front-end engineer) → Or request sponsorship for yourself Either way, you’re helping keep momentum alive in a tough market. 👉 Take action here: pastthebots.com/sponsor Let’s turn “I was laid off” into “Someone had my back.” Thank you for being part of this community, Rod Trent Past the Bots Subscribe with your favorite podcast player or watch on YouTube. About Ray Reyes Ray Reyes is a Principal Security Consultant at Engage Squared and the author of Mastering Microsoft Purview Deployment in the Era of AI. He previously worked at Microsoft, where he led data-security subject-matter expertise across Asia Pacific and Japan and helped customers deploy Microsoft Purview and Microsoft Defender XDR. His work now spans identity, data security, and the wider Microsoft security stack. * LinkedIn → linkedin.com/in/ray-reyes-598062125 Related Links * Mastering Microsoft Purview Deployment in the Era of AI by Ray Reyes (mentioned at 00:00 and 02:25) * Microsoft Purview overview (discussed from 03:29) * Adaptive Protection in Microsoft Purview (discussed at 22:09) * Learn about Data Loss Prevention for Network Data Security (discussed at 33:31) * Configure Microsoft Entra Internet Access content filtering (discussed at 34:18) * The Resilience Project: Finding Happiness through Gratitude, Empathy and Mindfulness by Hugh van Cuylenburg (mentioned at 47:25) Related Entra.Chat Episodes * How Microsoft Is Securing AI Agents in Entra — Conditional Access, Zero Trust & the “Block” Debate * How to Migrate from Legacy VPNs to Entra Private Access * What’s New in Microsoft Entra — May 2026: Passkeys, Agents & Cloud Sync Chapters 00:00 Intro 03:29 Why Purview Matters to Entra Admins 05:39 How Microsoft Purview Evolved 09:46 Data Loss Prevention Explained 16:04 Insider Risk and Employee Departures 22:09 Adaptive Protection Meets Conditional Access 25:00 Education and Alert Ownership 28:51 Breaking Down the Security Silos 33:31 Network Data Security and Unsanctioned AI 38:29 How to Roll Out Purview Safely 41:20 Ray’s Charity Work in Nepal 47:10 Resilience Burnout and a Career Safety Net 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

Xbox Security runs a gaming-specific Microsoft Entra baseline across more than 70 tenants every night. The scale is striking: about 50 controls, dozens of independently operated game-studio tenants, and one parallel pipeline that checks whether each environment still matches Xbox’s security intent. When a Conditional Access policy moves to report-only or a required service principal loses a permission, the next run finds it. In this episode of Entra.Chat, Merill speaks with Audrey Long, Principal Cloud Security Architect in Xbox Security at Microsoft, and Sam Erde, SecureShield Architect at Patriot Consulting and a Maester maintainer. Audrey explains how Xbox Security extended Maester with custom PowerShell, GitHub Actions, a multi-tenant service principal, federated identity credentials, dashboards, ticketing, and time-bound exceptions. The result is more than a posture report. Findings flow into an operational lifecycle with owners and deadlines. Studios get readable reports, deep links to the affected object, and remediation guidance. Security teams can answer audit questions without interrupting all the tenant admins, while the Maester pipeline keeps read-only observability separate from remediation authority. The conversation also covers why a Microsoft-wide baseline needs adapting for gaming acquisitions, how custom tests encode an organization’s intent, why security configuration deserves regression tests, the Investigate status Audrey’s team helped introduce, and how administrators can use AI as a first-draft assistant for PowerShell and CI/CD without outsourcing validation. Subscribe with your favorite podcast player or watch on YouTube Sponsor Maester Cloud turns every Maester and Microsoft Zero Trust Assessment run into a durable evidence trail. See new failures, fixes, accepted risks, and posture changes across every tenant—without digging through old HTML reports. * Keep 5+ years of tenant history in your chosen Azure region * Compare runs, spot drift, and get change alerts Maester Cloud is in active development. Join the waitlist for hosted, self-hosted, or enterprise onboarding updates. About Audrey Long Audrey Long is a Principal Cloud Security Architect in Xbox Security at Microsoft. She focuses on Microsoft Entra and identity security, as well as securing Azure, AWS, and Google Cloud environments across Xbox and its game studios. In this episode, she shares how her team built a gaming-specific Entra baseline and operationalized it across more than 70 tenants. * LinkedIn - https://www.linkedin.com/in/aulong/ About Sam Erde Sam Erde is part of the Maester core maintainer team, a Microsoft MVP, and a SecureShield Architect at Patriot Consulting. He focuses on Active Directory, Microsoft Entra ID, Microsoft 365 security, and practical PowerShell tooling for defenders. LinkedIn - https://www.linkedin.com/in/samerde/ Related Links * Maester, installation guide, and source code (mentioned at 02:19) - Maester · installation guide · GitHub source * Continuous monitoring with Maester and GitHub Actions (mentioned at 14:38) - https://maester.dev/docs/monitoring/github/ * Writing custom Maester tests (mentioned at 22:39) - https://maester.dev/docs/writing-tests/ * Connect-Maester permissions and read-only access (mentioned at 24:38) - https://maester.dev/docs/connect-maester/ * Zero Trust Assessment: Secure your tenant (mentioned at 25:46) - https://entra.news/p/find-your-tenants-hidden-flaws-in * Maester’s Investigate test-result status (mentioned at 34:02) - https://maester.dev/docs/writing-tests/formatting-test-results/ * Making Security Invisible for Game Developers (mentioned at 45:52) - https://opsmatters.com/videos/making-security-invisible-game-developers Related Entra.Chat Episodes * How to Secure Copilot Agents, Azure DevOps & Defender (+ more) with Maester 2.1 (Full Breakdown) * Zero Trust Assessment: Secure your tenant * How to Design Bullet-Proof Conditional Access Policies in Microsoft Entra ID Chapters 00:00 Intro00:42 Meet Audrey Long02:19 From 50 Controls to 70+ Tenants05:11 Making an Entra Baseline Gaming-Specific08:32 Why Custom Maester Tests Matter11:07 Governance and Nightly Automation15:27 From Findings to Remediation18:07 Reports Studios Can Actually Use22:39 Building Custom Multi-Tenant Tests28:07 Security Intent as Regression Tests30:48 Catching Drift and Producing Audit Evidence41:39 CI/CD and AI for Security Admins 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 Entra Agent ID uses familiar application and service-principal objects under the hood, but its one-to-many hierarchy creates a different security boundary. A blueprint can be associated with many agent identities. When that blueprint belongs to a third-party provider and is trusted across customer tenants, the provider’s credential security becomes part of every customer’s risk model. In this episode of Entra.Chat, Merill speaks with Katie Knowles, Senior Security Researcher at Datadog, about her three-part security analysis of Microsoft Entra Agent ID. Katie explains the blueprint, blueprint principal, agent identity, and agent-user relationships before walking through a cross-tenant compromise demonstration: compromised blueprint credentials, enumeration of associated agents, token requests in trusting tenants, permission inspection, and selection of a useful target identity. That path does not automatically grant Global Administrator access. Its impact depends on what the target agent identity has been permitted to do. The important lesson is the control point: one blueprint can sit upstream of many identities, tenants, and permission sets. Katie and Merill also discuss tenant-owned versus vendor-owned blueprints, the Agent ID Administrator role, first-party agent creation through Microsoft platforms, why production client secrets compound the blast radius, workload identity federation, separating blueprints by risk, reusing app-registration detections, and Microsoft Entra ID Protection for agents. REGISTER: Hidden Risk of App Permissions in Entra ID Many Microsoft Entra ID environments contain third-party and custom applications with permissions that are broader than necessary, and most organizations lack visibility into how those permissions are being used. Excessive Microsoft Graph permissions and unused access increase the risk of OAuth abuse and privilege escalation. Join our live session on July 22 to learn how to: * Evaluate delegated versus application permissions * Build an effective app governance strategy * Reduce unnecessary access without disrupting users You’ll also see how a free AppGov Score assessment can help identify governance gaps and where unused permissions reporting fit into a least-privilege approach. Subscribe with your favorite podcast player or watch on YouTube About Katie Knowles Katie Knowles is a Senior Security Researcher at Datadog focused on Azure security research, cloud identity, and securing emerging technologies. * LinkedIn - https://linkedin.com/in/kaknowles * X/Twitter - https://twitter.com/_sigil * GitHub - https://github.com/siigil * Website - https://kknowl.es/ * Microsoft MVP profile - https://mvp.microsoft.com/en-US/MVP/profile/a3547b6a-6a4d-4aa0-840f-23b858c43c8b Related Links * Entra Agent ID: The blueprint blast radius (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-blueprint-blast-radius/ * Entra Agent ID: Inside a cross-tenant agent compromise (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-inside-agent-compromise/ * Entra Agent ID: Protect, detect, respond (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-protect-detect-respond/ * Disable agent identities in your tenant (mentioned at 04:00 and 49:33) - https://learn.microsoft.com/entra/agent-id/disable-agent-identities * Investigating suspicious AI workflows in Microsoft Entra Agent ID: Agent’s user account (mentioned at 05:14) - https://redcanary.com/blog/threat-detection/entra-id-ai-workflows-teams/ * Entra Agent ID from a Security Perspective (mentioned at 20:38) - https://blog.compass-security.com/2026/06/entra-agent-id-from-a-security-perspective/ * Spying On Your ISVs Credential Choices (mentioned at 38:11) - https://ericonidentity.com/2025/01/13/spying-on-your-isvs-credential-choices/ * Who Are the Robots? Uncovering AI Agents Identities (mentioned at 51:39) - https://www.youtube.com/watch?v=mMxACHKIAwY * AzTier (mentioned at 51:39) - https://aztier.com/ * Microsoft Entra Agent ID key concepts - https://learn.microsoft.com/entra/agent-id/key-concepts * Workload identity federation - https://learn.microsoft.com/entra/workload-id/workload-identity-federation * ID Protection for agents - https://learn.microsoft.com/entra/id-protection/concept-risky-agents Related Entra.Chat Episodes * If You Manage Entra Permissions, Watch This Before Deploying Agents - https://entra.news/p/if-you-manage-entra-permissions-watch * 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 Ecosystem You Cannot See - https://entra.news/p/attackers-are-targeting-the-ai-ecosystem Chapters 00:00 Intro 01:12 Katie’s Three-Part Agent ID Research 05:40 Agent ID Objects Under the Hood 06:24 One Blueprint, Many Agent Identities 08:43 The Multitenant Trust Boundary 17:33 Cross-Tenant Compromise Walkthrough 28:29 First-Party and Third-Party Blueprints 36:56 Stop Using Client Secrets 38:40 Workload Identity Federation 46:24 Permissions and Privilege Boundaries 49:33 Detecting and Responding to Agent Abuse 51:29 What Comes Next for Agent ID 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

AI agent security is not just about attackers using AI. It is also about attackers targeting the agent ecosystem most organizations cannot see clearly yet: MCP servers, agent skills, packages, API keys, prompts, tools, and the identity layer underneath all of it. In this episode, I sit down with Thomas Roccia, founder of Security Break and a former Microsoft threat researcher, to look at AI agents from the threat-intelligence side. Thomas explains why the easiest path for attackers may not be futuristic autonomous hacking. It may be the boring weak spots that already exist: malicious packages, untrusted MCP servers, hostile agent skills, leaked API keys, and AI-generated code that chooses the fastest path instead of the safest one. For Entra admins and security teams, this is where Agent ID, non-human identity, workload identity, logging, sponsorship, and governance start to matter. Entra Agent ID gives teams a way to identify and govern agents, but identity is only one part of the picture. You still need to understand what agents can discover, what tools they can call, what context they consume, and whether you can replay what they actually did. Thomas also breaks down his practical AI threat-intelligence work, including how teams can use agents for CTI, how adversarial prompts and context flooding change the risk model, and why defenders need to understand the attacker side of agent security before these systems become invisible production infrastructure. Sponsored by Secure BYOD Wi‑Fi Without MDM enrollment Keytos Connect is a new mobile and desktop app that makes it easy for users to connect personal and BYOD devices to enterprise and campus Wi‑Fi without shared passwords, manual certificate installs, or traditional MDM enrollment. Users simply download the app, sign in with their work or school account, and Keytos handles the rest. It also works alongside Intune, allowing organizations to continue managing corporate-owned devices while simplifying connectivity for personal devices. * Connect in minutes: users download the app, sign in, and get securely onboarded to Wi‑Fi * No MDM required: enable secure access for personal devices without giving IT full control of them * Works alongside Intune: keep your existing management workflows for corporate devices while enabling secure BYOD access * Automatic certificate management: certificate issuance and renewal happen behind the scenes * Secure by default: EAP-TLS authentication eliminates shared Wi‑Fi passwords and provides unique credentials for every user * Multi-OS: Available across iOS, Android, Windows, and macOS devices * Included at no additional cost with existing EZRADIUS and EZCA subscriptions Learn more about Keytos Connect and see how easy secure BYOD connectivity can be. About Thomas Roccia Thomas Roccia is a threat researcher and founder of SecurityBreak, focused on AI threat intelligence, malware analysis, and AI agent security. He previously worked in incident response, malware analysis, threat intelligence, Microsoft Defender, and AI threat research. He is also the author of Visual Threat Intelligence and teaches practical AI for threat intelligence and agentic workflows. LinkedIn - https://au.linkedin.com/in/thomas-roccia Subscribe with your favorite podcast player or watch on YouTube 👇 Related Links * Thomas Roccia on LinkedIn - https://au.linkedin.com/in/thomas-roccia * SecurityBreak - https://securitybreak.io/ * Practical AI for Threat Intelligence training - https://securitybreak.io/training-genai * SHIELD.md: A Security Standard for OpenClaw and AI Agents - https://blog.securitybreak.io/shield-md-a-security-standard-for-openclaw-and-ai-agents-b38637031460 * Microsoft Entra Agent ID - https://learn.microsoft.com/en-us/entra/agent-id/what-is-microsoft-entra-agent-id * Microsoft Entra Agent ID key concepts - https://learn.microsoft.com/en-us/entra/agent-id/key-concepts * Agentic Resource Discovery specification - https://agenticresourcediscovery.org/ * GitHub Agent Finder - https://github.blog/changelog/2026-06-17-agent-finder-for-github-copilot-now-available/ Chapters 00:00 Intro 00:33 Meet Thomas Roccia 01:48 From Malware Analysis to AI Threat Intel 03:30 Why AI Security Is Moving So Fast 05:49 Agentic Resource Discovery and New Standards 09:25 Attackers Are Already Using AI Agents 11:47 The AI Ecosystem Is The Target 15:26 Prompt Injection, MCP, Skills, and API Keys 20:28 Vibe Coding vs Production Security 23:47 Agent ID and Identity for AI Agents 32:30 Practical AI for Threat Intelligence 39:13 Monitoring Agents Like Threat Actors Do 42:28 Context Flooding and What’s Next 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