Moving Microsoft 365 authentication to Entra ID Cloud Auth from On-Prem ADFS
Hi Identity Brain Trust, Assuming this would be the right place for my question as I couldn't find any other hub more relevant for this one. We have several applications configured to be authenticated via ADFS. We are looking to move these gradually to Entra ID Cloud auth and decommission ADFS, eventually. I would like to test out how Microsoft 365 can be moved to Cloud Auth from ADFS for a certain group of people. I have tried to use ADFS migration wizard in Entra but 365 app is not showing in the ADFS Application Migration section of Entra ID. I've read this official guide but still couldn't find how this can be manually done when App Migration section won't have the app appearing there. - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/migrate-ad-fs-application-overview Appreciate any of your inputs on this one! Kev
MFA Issue blocks Global Admin / Data Protection Team disconnects calls
Hi. I have just learned that the Microsoft Authenticator app allows you to create MFA for multiple Global Administrator accounts, but those accounts will not properly transfer when you move to a new Smartphone. I have one tenant that has only one Global Admin Account secured using MFA and the Microsoft Authenticator App. The MFA is no longer working. I have been told to work with the Microsoft Data Protection Team by calling them at 800-865-9408. The weird thing is they keep disconnecting the call before the issue gets addressed. It has happened multiple times. Calling them back results in hold times averaging over 2 hours. Does anyone have ideas how I can get my MFA issue solved perhaps by reaching the proper group at Microsoft in another fashion? Is there some customer advocate resource at Microsoft I can contact?
From “No” to “Now”: A 7-Layer Strategy for Enterprise AI Safety
The “block” posture on Generative AI has failed. In a global enterprise, banning these tools doesn't stop usage; it simply pushes intellectual property into unmanaged channels and creates a massive visibility gap in corporate telemetry. The priority has now shifted from stopping AI to hardening the environment so that innovation can run at velocity without compromising data sovereignty. Traditional security perimeters are ineffective against the “slow bleed” of AI leakage - where data moves through prompts, clipboards, and autonomous agents rather than bulk file transfers. To secure this environment, a 7-layer defense-in-depth model is required to treat the conversation itself as the new perimeter. 1. Identity: The Only Verifiable Perimeter Identity is the primary control plane. Access to AI services must be treated with the same rigor as administrative access to core infrastructure. The strategy centers on enforcing device-bound Conditional Access, where access is strictly contingent on device health. To solve the "Account Leak" problem, the deployment of Tenant Restrictions v2 (TRv2) is essential to prevent users from signing into personal tenants using corporate-managed devices. For enhanced coverage, Universal Tenant Restrictions (UTR) via Global Secure Access (GSA) allows for consistent enforcement at the cloud edge. While TRv2 authentication-plane is GA, data-plane protection is GA for the Microsoft 365 admin center and remains in preview for other workloads such as SharePoint and Teams. 2. Eliminating the Visibility Gap (Shadow AI) You can’t secure what you can't see. Microsoft Defender for Cloud Apps (MDCA) serves to discover and govern the enterprise AI footprint, while Purview DSPM for AI (formerly AI Hub) monitors Copilot and third-party interactions. By categorizing tools using MDCA risk scores and compliance attributes, organizations can apply automated sanctioning decisions and enforce session controls for high-risk endpoints. 3. Data Hygiene: Hardening the “Work IQ” AI acts as a mirror of internal permissions. In a "flat" environment, AI acts like a search engine for your over-shared data. Hardening the foundation requires automated sensitivity labeling in Purview Information Protection. Identifying PII and proprietary code before assigning AI licenses ensures that labels travel with the data, preventing labeled content from being exfiltrated via prompts or unauthorized sharing. 4. Session Governance: Solving the “Clipboard Leak” The most common leak in 2025 is not a file upload; it’s a simple copy-paste action or a USB transfer. Deploying Conditional Access App Control (CAAC) via MDCA session policies allows sanctioned apps to function while specifically blocking cut/copy/paste. This is complemented by Endpoint DLP, which extends governance to the physical device level, preventing sensitive data from being moved to unmanaged USB storage or printers during an AI-assisted workflow. Purview Information Protection with IRM rounds this out by enforcing encryption and usage rights on the files themselves. When a user tries to print a "Do Not Print" document, Purview triggers an alert that flows into Microsoft Sentinel. This gives the SOC visibility into actual policy violations instead of them having to hunt through generic activity logs. 5. The “Agentic” Era: Agent 365 & Sharing Controls Now that we're moving from "Chat" to "Agents", Agent 365 and Entra Agent ID provide the necessary identity and control plane for autonomous entities. A quick tip: in large-scale tenants, default settings often present a governance risk. A critical first step is navigating to the Microsoft 365 admin center (Copilot > Agents) to disable the default “Anyone in organization” sharing option. Restricting agent creation and sharing to a validated security group is essential to prevent unvetted agent sprawl and ensure that only compliant agents are discoverable. 6. The Human Layer: “Safe Harbors” over Bans Security fails when it creates more friction than the risk it seeks to mitigate. Instead of an outright ban, investment in AI skilling-teaching users context minimization (redacting specifics before interacting with a model) - is the better path. Providing a sanctioned, enterprise-grade "Safe Harbor" like M365 Copilot offers a superior tool that naturally cuts down the use of Shadow AI. 7. Continuous Ops: Monitoring & Regulatory Audit Security is not a “set and forget” project, particularly with the EU AI Act on the horizon. Correlating AI interactions and DLP alerts in Microsoft Sentinel using Purview Audit (specifically the CopilotInteraction logs) data allows for real-time responses. Automated SOAR playbooks can then trigger protective actions - such as revoking an Agent ID - if an entity attempts to access sensitive HR or financial data. Final Thoughts Securing AI at scale is an architectural shift. By layering Identity, Session Governance, and Agentic Identity, AI moves from being a fragmented risk to a governed tool that actually works for the modern workplace.
Windows Hello passkeys dialog appearing and cannot remove or suppress it.
Hi everyone, I’m dealing with a persistent Windows Hello and passkey issue in Chrome and Brave and yes this is relevant as they're the only browsers having this issue whilst Edge for example is fine, and at this point I’m trying to understand whether this is expected behavior, a bug, or a design oversight. PS. Yes, I'm in contact with related browser support teams but since they seem utterly hopeless i'm asking here, since its at least partially Windows Hello issue. Problem description Even with: Password managers disabled in browser settings, Windows Hello disabled in Chrome/Brave settings, Windows Hello PIN enabled only for device login, Passkeys still stored under chrome://settings/passkeys (which I cannot delete since its used for logging on the device), The devices are connected to Entra ID but this is not required to reproduce the issue although a buisness account configuration creates a Passkey with Windows Hello afaik. Observed behavior When I attempt to sign in on office.com, Windows Hello automatically triggers a dialog offering authentication via passkeys, even though: I don’t want passkeys used for browser logins, passkeys are turned off everywhere they can be, Windows Hello is intended only for local device authentication. The dialog cannot be suppressed, disabled, or hidden(trust me, i tried for weeks). It effectively forces the Windows Hello prompt as a primary option, which causes problems both personally and in business contexts (wrong credential signaling, misleading users that are supposed to use a dedicated password manager solution insted of browser password managers, enforcing an unwanted authentication flow, etc.). What I already verified Many, many, (too many) Windows registry workarounds that never worked. Dug through almost all flags on those browsers. Chrome/Brave → Password Manager: disabled Chrome/Brave → Windows Hello toggle: off Looked through what feels like almost every related option in Windows Settings. Tried gpedit.msc local rules System up to date Windows Hello configured to use PIN, but stores "passkeys used to log on to this device" Why this is a problem Windows Hello automatically assumes that the device-level Windows Hello credentials should always be available as a WebAuthn authenticator. This feels like a big security and UX issue due to: unexpected authentication dialogs, Inability to controll where and how passkey credential are shared to applications, inability to turn the feature off, no administrative or local option to disable Hello for WebAuthn separately from device login. Buisness users either having issues with keeping passwords in order (our buissnes uses a dedicated Password Manager but this behaviour covers its dialog option) or not having PIN to their devices (when I disable windows hello entierly, since when there is no passkeys the option doesn't appear) Questions Is there any supported way to disable Windows Hello as a WebAuthn/passkey option in browsers, while keeping Hello enabled for local device login? Is this expected behavior from the Windows Hello, or is it considered a bug? Are there registry/policy settings (documented or upcoming) that allow disabling the Windows platform authenticator specifically for browsers like Chrome and Brave? Is Microsoft aware of this issue? If so, is it tracked anywhere? Additional notes This issue replicates 100% across (as long as there are passkeys configured): Windows 11 devices i've managed to get my hands on, Chrome and Brave (latest versions), multiple Microsoft accounts and tenants, multiple clean installations. Any guidance or clarification from the Windows security or identity teams would be greatly appreciated. And honestly if there is any more info i could possibly provide PLEASE ask away.
Survey: Microsoft Purview Retention Labels in Outlook Mobile (iOS/Andriod)
We need your input! Today, in Outlook for Windows, Outlook for the Web, and (currently rolling out) Outlook for Mac, end-users can manually apply Microsoft Purview retention labels and MRM personal tags to individual emails and non-default (user-created) folders. The Outlook and Data Lifecycle Management product groups are interested in learning from our customers how important that same functionality would be in Outlook for Mobile (iOS/Android). Please consider filling out and sharing the following survey to let us know how this feature would or would not be useful to you and your organization: https://aka.ms/RetentionLabels-OutlookMobile Please note that your responses will remain anonymous unless you choose to provide contact information at the end of the survey.Never Get Locked Out: The Importance of a Break Glass Admin Account
One of the simplest but most critical safeguards in Microsoft Entra ID is having a Break Glass Admin account. In my lab, I created a dedicated emergency account with: - Permanent Global Admin role (for emergencies only) - Excluded from Conditional Access policies - Strong password stored securely - Monitoring in place to detect any sign-in attempts This account is never used for daily operations — it exists only to guarantee access in case Conditional Access, MFA, or identity protection policies block all other admins. This setup prevents accidental lockouts and ensures continuity. Does your organization maintain a Break Glass Admin account, and how do you secure it?
Getting Contextual Summary from SIT(Sensitive info types) via PowerShell cmd
Hi, I am using a PowerShell command(Export-ContentExplorerData) to extract data from an SIT. In the response, I am getting most of the data but I am interested in getting the matching primary element from Contextual summary(Content explorer) https://learn.microsoft.com/en-us/powershell/module/exchange/export-contentexplorerdata
Scheduling attack simulations
I'm starting to use the Defender attack simulation feature. I have approx. 3000 users to target. Leadership don't want to send 3000 tests every month rather divide the people up across 12 months sending smaller monthly batches. The issue of not being enough tests for each individual is there a way to automate the sending of these to even batches of people across 12 months rather than having to set these up manually?
Device Stuck on Restart Screen After Update - Error Code: ATTEMPTED WRITE TO READONLY MEMORY
Hi everyone, I’m experiencing an issue with my Windows device that started after a recent update. For the past three days, my device has been stuck on a restart screen with the following error message: Your device ran into a problem and needs to restart. We'll restart for you. For more information about this issue and possible fixes, visit https://www.windows.com/stopcode If you call a support person, give them this info: Stop Code: ATTEMPTED WRITE TO READONLY MEMORY I’ve tried restarting the device multiple times, but it keeps returning to this screen. I’m unable to access my system or troubleshoot further. Has anyone else encountered this issue after an update? Any suggestions on how to resolve this would be greatly appreciated. Thank you in advance for your help!
