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.
Enterprise Strategy for Secure Agentic AI: From Compliance to Implementation
Imagine an AI system that doesn’t just answer questions but takes action querying your databases, updating records, triggering workflows, even processing refunds without human intervention. That’s Agentic AI and it’s here. But with great power comes great responsibility. This autonomy introduces new attack surfaces and regulatory obligations. The Model Context Protocol (MCP) Server the gateway between your AI agent and critical systems becomes your Tier-0 control point. If it fails, the blast radius is enormous. This is the story of how enterprises can secure Agentic AI, stay compliant and implement Zero Trust architectures using Azure AI Foundry. Think of it as a roadmap a journey with three milestones - Milestone 1: Securing the Foundation Our journey starts with understanding the paradigm shift. Traditional AI with RAG (Retrieval-Augmented Generation) is like a librarian: It retrieves pre-indexed data. It summarizes information. It never changes the books or places orders. Security here is simple: protect the index, validate queries, prevent data leaks. But Agentic AI? It’s a staffer with system access. It can: Execute tools and business logic autonomously. Chain operations: read → analyze → write → notify. Modify data and trigger workflows. Bottom line: RAG is a “smart librarian.” Agentic AI is a “staffer with system access.” Treat the security model accordingly. And that means new risks: unauthorized access, privilege escalation, financial impact, data corruption. So what’s the defense? Ten critical security controls your first line of protection: Here’s what a production‑grade, Zero Trust MCP gateway needs. Its intentionally simplified in the demo (e.g., no auth) to highlight where you must harden in production. (https://github.com/davisanc/ai-foundry-mcp-gateway) Authentication Demo: None Prod: Microsoft Entra ID, JWT validation, Managed Identity, automatic credential rotation Authorization & RBAC Demo: None Prod: Tool‑level RBAC via Entra; least privilege; explicit allow‑lists per agent/capability Input Validation Demo: Basic (ext whitelist, 10MB, filename sanitize) Prod: JSON Schema validation, injection guards (SQL/command), business‑rule checks Rate Limiting Demo: None Prod: Multi‑tier (per‑agent, per‑tool, global), adaptive throttling, backoff Audit Logging Demo: Console → App Service logs Prod: Structured logs w/ correlation IDs, compliance metadata, PII redaction Session Management Demo: In‑memory UUID sessions Prod: Encrypted distributed storage (Redis/Cosmos DB), tenant isolation, expirations File Upload Security Demo: Ext whitelist, size limits, memory‑only Prod: 7‑layer defense (validate, MIME, malware scanning via Defender for Storage), encryption at rest, signed URLs Network Security Demo: Public App Service + HTTPS Prod: Private Endpoints, VNet integration, NSGs, Azure Firewall no public exposure Secrets Management Demo: App Service env vars (not in code) Prod: Azure Key Vault + Managed Identity, rotation, access audit Observability & Threat Detection (5‑Layer Stack) Layer 1: Application Insights (requests, dependencies, custom security events) Layer 2: Azure AI Content Safety (harmful content, jailbreaks) Layer 3: Microsoft Defender for AI (prompt injection incl. ASCII smuggling, credential theft, anomalous tool usage) Layer 4: Microsoft Purview for AI (PII/PHI classification, DLP on outputs, lineage, policy) Layer 5: Microsoft Sentinel (SIEM correlation, custom rules, automated response) Note: Azure AI Content Safety is built into Azure AI Foundry for real‑time filtering on both prompts and completions. Picture this as an airport security model: multiple checkpoints, each catching what the previous missed. That’s defense-in-depth. Zero Trust in Practice ~ A Day in the Life of a Prompt Every agent request passes through 8 sequential checkpoints, mapped to MITRE ATLAS tactics/mitigations (e.g., AML.M0011 Input Validation, AML.M0004 Output Filtering, AML.M0015 Adversarial Input Detection). The design goal is defense‑in‑depth: multiple independent controls, different detection signals, and layered failure modes. Checkpoints 1‑7: Enforcement (deny/contain before business systems) Checkpoint 8: Monitoring (detect/respond, hunt, learn, harden) AML.M0009 – Control Access to ML Models AML.M0011 – Validate ML Model Inputs AML.M0000 – Limit ML Model Availability AML.M0014 – ML Artifact Logging AML.M0004 – Output Filtering AML.M0015 – Adversarial Input Detection If one control slips, the others still stand. Resilience is the product of layers. Milestone 2: Navigating Compliance Next stop: regulatory readiness. The EU AI Act is the world’s first comprehensive AI law. If your AI system operates in or impacts the EU market, compliance isn’t optional, it’s mandatory. Agentic AI often falls under high-risk classification. That means: Risk management systems. Technical documentation. Logging and traceability. Transparency and human oversight. Fail to comply? Fines up to €30M or 6% of global turnover. Azure helps you meet these obligations: Entra ID for identity and RBAC. Purview for data classification and DLP. Defender for AI for prompt injection detection. Content Safety for harmful content filtering. Sentinel for SIEM correlation and incident response. And this isn’t just about today. Future regulations are coming US AI Executive Orders, UK AI Roadmap, ISO/IEC 42001 standards. The trend is clear: transparency, explainability, and continuous monitoring will be universal. Milestone 3: Implementation Deep-Dive Now, the hands-on part. How do you build this strategy into reality? Step 1: Entra ID Authentication Register your MCP app in Entra ID. Configure OAuth2 and JWT validation. Enable Managed Identity for downstream resources. Step 2: Apply the 10 Controls RBAC: Tool-level access checks. Validation: JSON schema + injection prevention. Rate Limiting: Express middleware or Azure API Management. Audit Logging: Structured logs with correlation IDs. Session Mgmt: Redis with encryption. File Security: MIME checks + Defender for Storage. Network: Private Endpoints + VNet. Secrets: Azure Key Vault. Observability: App Insights + Defender for AI + Purview + Sentinel. Step 3: Secure CI/CD Pipelines Embed compliance checks in Azure DevOps: Pre-build: Secret scanning. Build: RBAC & validation tests. Deploy: Managed Identity for service connections. Post-deploy: Compliance scans via Azure Policy. Step 4: Build the 5-Layer Observability Stack App Insights → Telemetry. Content Safety → Harmful content detection. Defender for AI → Prompt injection monitoring. Purview → PII/PHI classification and lineage. Sentinel → SIEM correlation and automated response. The Destination: A Secure, Compliant Future By now, you’ve seen the full roadmap: Secure the foundation with Zero Trust and layered controls. Navigate compliance with EU AI Act and prepare for global regulations. Implement the strategy using Azure-native tools and CI/CD best practices. Because in the world of Agentic AI, security isn’t optional, compliance isn’t negotiable, and observability is your lifeline. Resources https://learn.microsoft.com/en-us/azure/ai-foundry/what-is-azure-ai-foundry https://learn.microsoft.com/en-us/azure/defender-for-cloud/ai-threat-protection https://learn.microsoft.com/en-us/purview/ai-microsoft-purview https://atlas.mitre.org/ https://digital-strategy.ec.europa.eu/en/policies/european-approach-artificial-intelligence https://techcommunity.microsoft.com/blog/microsoft-security-blog/microsoft-sentinel-mcp-server---generally-available-with-exciting-new-capabiliti/4470125Never 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?
Authenticator not displaying numbers on MacOS
I'm have an issue with MFA on a Mac (all the latest versions). We have conditional access policies in place, so once a day I'm prompted for MFA (I work off-site) and the Office app (e.g. Outlook, Teams) will create the pop-up window that 'should' display a number that I then match on my phone. My phone see's the push notification, but the Mac never creates the numbers in the first place. The pop-up is there, just no number. The workaround is: Answer 'its not me' on the phone On the Mac, select 'I can't use Authenticator right now' Tell the Mac to send a new request This time it creates the number and I can authenticate on the phone. It only appears to happen for the installed Office applications i.e. if I'm accessing applications/admin-centre via the browser, then the pop-up is within the browser and everything works first time. Is this a known issue?Meet Your New Cybersecurity Sidekick - Microsoft Security Copilot Agents
Imagine if your security team had a super-smart assistant that never sleeps, learns from every task, and helps stop cyber threats before they become disasters. That’s exactly what Microsoft’s new Security Copilot Agents are designed to do. Why Do We Need Them? Cyberattacks are getting sneakier and faster many now use AI to trick people or break into systems. In fact, 67% of phishing attacks in 2024 used AI. Meanwhile, security teams are drowning in alerts 66 per day on average and 73% of experts admit they’ve missed important ones. That’s where Security Copilot comes in. It’s like having an AI-powered teammate that helps you investigate threats, fix issues, and stay ahead of attackers. What Are Security Copilot Agents? Think of these agents as mini digital coworkers. They’re not just chatbots they’re smart, adaptable tools that: Learn from your feedback Work with your existing Microsoft security tools Help you make faster, better decisions Keep you in control while they handle the heavy lifting They’re built to be flexible and smart unlike traditional automation that breaks when things change. Real-World Examples of What They Do Here are a few of the agents already available: Phishing Triage Agent: Automatically checks if a suspicious email is a real threat or just spam. It explains its reasoning in plain language and learns from your feedback. Alert Triage Agents (in Microsoft Purview): Helps prioritize which security alerts matter most, so your team can focus on the big stuff first. Conditional Access Optimization Agent (in Microsoft Entra): Keeps an eye on who has access to what and flags any gaps in your security policies. Vulnerability Remediation Agent (in Microsoft Intune): Spots the most urgent software vulnerabilities and tells you what to fix first. Threat Intelligence Briefing Agent: Gives you a quick, customized report on the latest threats that could affect your organization. Even More Help from Partners Microsoft is also teaming up with other companies to build even more agents. For example: OneTrust helps with privacy breach responses. Tanium helps analysts make faster decisions on alerts. Fletch helps reduce alert fatigue by showing what’s most important. Aviatrix helps diagnose network issues like VPN or gateway failures. BlueVoyant: helps to assess your SOC and recommends improvements. Why It Matters These agents don’t just save time they help your team stay ahead of threats, reduce stress, and focus on what really matters. They’re like having a team of AI-powered interns who never get tired and are always learning. Learn More 📢 Microsoft Security Blog: Security Copilot Agents Launch 🎥 https://aka.ms/SecurityCopilotAgentsVideo
Entra Private Access - Private DNS
Hello Everyone We are using the trial period of Entra Private access and Entra Internet Access using Global Secure Access client. We recently got the Private DNS feature within Quick Access under Global Secure Access. The moment, we added our on-premise domain suffix to create a line of sight to the DC's, access to other private apps, some of which are actually cloud web apps stopped working. The cloud app web portals won't open, RDP to servers were not working. Intermittently, we could open the portal or RDP to the server, but everything had just died down. After leaving it for more than 8 hours, the issues were still not going away, so we removed the quick access app and disabled private DNS, issue was resolved after that. Any ideas why ? Also, is there a way we could allow our on-premise user accounts to change their passwords when it expires or get those password expired notifications as we did when we used Cisco VPN. We have Azure hybrid-joined machines with GSA running in them, but users don't get password expiry notifications, nor can they change the password on the local Laptop as it can't talk to the DC's. We created an app with Kerberos port 88, LDAP 389 and 464, still password change doesn't work. Users are logging in to the Laptops with cached passwords.Anomalies with Conditional Access Policy "Terms of Use" Failures
Hello Microsoft Community, I'm reaching out with a bit of a puzzle regarding our "Terms of Use" Conditional Access policy, and I'm eager to tap into the collective wisdom here for some insights. In our Entra ID User Sign-In logs, we've identified intermittent "failure" entries associated with the "Terms of Use" Conditional Access policy. Interestingly, even for users who had previously accepted the "Terms of Use". There appears to be no discernible impact, and they continue their tasks without interruption. This observation became apparent during the troubleshooting of unrelated Surface Hub and Edge Sync issues at some client sites. What adds to the complexity of the situation is that for the same users, both before and after these "failure" entries, the Conditional Access policy is marked as "success". Hence, it doesn't seem to be a straightforward case of the policy erroneously detecting non-acceptance of the "Terms of Use". The mystery lies in understanding why these intermittent "failure" entries occur for users who have already accepted the terms, especially when the policy consistently reports "success" for the same users. Furthermore, the Insights for the "Terms of Use" Conditional Access policy show around 1.48k successes and 1.43k failures in the last 90 days, yet there's no discernible impact on user functionality. Observations: "Failure" entries in Sign-In logs don't seem to disrupt users' day-to-day activities. The ratio of successes to failures is balanced, yet users experience no noticeable problems. The issue complicates troubleshooting efforts but doesn't significantly affect the user experience. I'm turning to the community for guidance on interpreting and resolving this discrepancy between "failure" entries in the Conditional Access policy logs and the seemingly unaffected user experience. Any insights into why these failures occur without user impact would be greatly appreciated. For additional context, I've attached screenshots of a user's Sign-In log entry and the insight chart from the Conditional Access policy. Sign-In log of a user (failure): Sign-In log of same user (success): Current Conditional Access insights: Thank you in advance for your time and assistance. I look forward to any guidance or solutions you can provide. Best regards, Leon TüpkerSecure Score - Enable conditional access policies to block legacy authentication.
Hi all, it reports me to block legacy authentications for all users, however I have already done so by configuring conditional access; does anyone else have the same report despite the fact that we have already implemented blocking?Cloud Kerberos - Failed to read secrets from the domain
Hi all, Apologies if this is the wrong place to post this! I am looking at understanding Cloud Kerberos and the uses behind it, primarily for WHfB for now. Following the guide on the Microsoft page, I get an error when running on the DC https://learn.microsoft.com/en-us/entra/identity/authentication/howto-authentication-passwordless-security-key-on-premises#install-the-azure-ad-kerberos-powershell-module?WT.mc_id=EM-MVP-5004668 Set-AzureADKerberosServer : Failed to read secrets from the domain DOMAIN.LOCAL. The lab environment has 2 DCs at different sites but replicate between each other without issue. The process creates an entry in AD but when I run the command below (GA details is an address, just changed for the forum post) Get-AzureADKerberosServer -Domain $domain -UserPrincipalName "GA details" -DomainCredential $domainCred I get the output below... Id : 16451 UserAccount : CN=krbtgt_AzureAD,CN=Users,DC=DOMAIN,DC=LOCAL ComputerAccount : CN=AzureADKerberos,OU=Domain Controllers,DC=DOMAIN,DC=LOCAL DisplayName : krbtgt_16451 DomainDnsName : DOMAIN.LOCAL KeyVersion : 1598799 KeyUpdatedOn : 27/07/2024 06:41:15 KeyUpdatedFrom : PDC.DOMAIN.LOCAL CloudDisplayName : CloudDomainDnsName : CloudId : CloudKeyVersion : CloudKeyUpdatedOn : CloudTrustDisplay : Can you advise why the secrets aren't being found and the cloud information not populated? This is a lab enviroment so if needed, we can get a bit rough with it. Any help would be welcomed. Kind regards Tom
