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!Blocking Personal Outlook and Gmail Accounts on Corporate Device
Hello Community, In my organization, we use the Microsoft 365 environment. We have a hybrid infrastructure, but we aim to deploy as many policies as possible through Microsoft 365 (Intune, Purview, Defender, etc.). One of our goals is to limit the use of corporate devices for personal purposes. We use Outlook as our corporate email service, and we would like to block employees from signing into their personal email accounts (either via web or desktop application). Additionally, we would like to block access to other email services, such as Gmail, both via web and desktop apps. Could you provide guidance on how to achieve this? I would greatly appreciate any help or suggestions. Thank you very much! Juan Rojas
User app registration - exploitable for BEC?
Hello. Recently dealt with a case of BEC. I'm not trained in forensics, but doing my best. Appears the hacker used an application called eM Client for their attack, getting access to a user's mailbox and hijacking a thread. I can see the login from two weeks ago (the incident was only noticed a couple days ago, however) - from a European country that SHOULD have been blocked by Conditional Access. Come to find out, the tenant conditional access was unassigned from everyone. We're not sure how - we re-enabled it, and audited changes, but the only change that appears was us re-enabling it. Which I thought indicates it was never configured right, except we've got a ticket documenting a change to Conditional Access a couple days after the hack that ALSO does not appear in the logs. So... it's likely it was changed, yet I have no record of that change (atleast, not through Entra > Monitoring > Auditing). If anyone knows any other ways of checking this, please advise - but I can't seem to even access our Diagnostic settings, the page tells me I need an Azure Active Directory subscription (I'm on Entra ID P1, which includes AAD.... this might be related to being global admin, and not Security Admin - we don't use that role in this relationship) ANYWAY, my amateur forensic skills have found that the attacker used an app called eM Client to get access. I'm not sure yet how they obtained the password, and got past MFA... But quick research shows this application (esp it's pro version) is known for use in BEC. The app was registered in Entra, and granted certain read permissions in Entra ID for shared mailboxes, presumably to find a decent thread to hijack. I'm not 100% sure yet there was any actual exploit done using this app, but it's popularity amongst hackers implies it does SOMETHING useful (i think remember that it authenticates using Exchange Web Services instead of Exchange Online, or something similar? Will update when I have the chance to check). We're in the process of improving our Secure Score, and this incident makes me think user's ability to register apps should be locked down. Checked Secure Score for this, and while there ARE recommendations around apps, disabling user app registration is NOT one of them. Just curious about people's thoughts. I just barely understand App Registration in Entra, but if this is a known attack vector, I would think disabling app registration would be a security recommendation?
