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.
Security Info blocked by conditional access
Hello, We have a conditional access policy in place where a specific group can only access Microsoft 365 (deny all apps, except Office 365). The moment a user clicks on Security Info in My Account, the user is blocked by this policy. I cant find a way to exclude the app "My Signins" (AppId 19db86c3-b2b9-44cc-b339-36da233a3be2). Since MFA is forced for this group, they can't change their authenticator app registration. Is there a solution for this? Initial MFA setup works by the way. UPDATE jan 23, 2025: I contacted Microsoft support and this was their answer (in short): " MySignin is a very sensitive resource that is not available in the picker and cannot be excluded in the conditional access policy. Also, the application is calling Microsoft Graph. I understand that this is not the information you are looking to hear at this time, I would have loved to help but the application cannot be excluded from the policy. "Entra External ID email OTP send event requestType always set to "signIn" regardless of user action
Hi, In a recent workload, I'm assisting a client with implementation of Entra External ID for identity management and app authentication, which includes sending OTP codes with customized email templates. To accomplish this, a custom authentication extension has been created that authorizes the request and then communicates with an email service via an event-driven, loosely coupled architecture. While implementing and testing this feature together with the client, we noticed that it seems like the different modes or states in the user flows are not reflected in the requestType property in the request payload posted to the OnOtpSend auth extension configured. E.g., if a user tries to sign in but has forgotten their password and navigates to the password reset view and requests to send the OTP code to their email address to reset the password, the following payload is sent to the auth extension endpoint (the original payload below was logged with Application Insights, with identifiers below then redacted and formatted, otherwise intact): { "type": "microsoft.graph.authenticationEvent.emailOtpSend", "source": "/tenants/aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee/applications/11111111-2222-3333-4444-555555555555", "data": { "@odata.type": "microsoft.graph.onOtpSendCalloutData", "otpContext": { "identifier": "email address removed for privacy reasons", "oneTimeCode": "<REDACTED>" }, "tenantId": "aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee", "authenticationEventListenerId": "22222222-3333-4444-5555-666666666666", "customAuthenticationExtensionId": "33333333-4444-5555-6666-777777777777", "authenticationContext": { "correlationId": "44444444-5555-6666-7777-888888888888", "client": { "ip": "192.0.2.10", "locale": "en-gb", "market": "en-gb" }, "protocol": "UNDEFINED", "requestType": "signIn", "clientServicePrincipal": { "id": "55555555-6666-7777-8888-999999999999", "appId": "11111111-2222-3333-4444-555555555555", "appDisplayName": "Example Web App", "displayName": "Example Web App" }, "resourceServicePrincipal": { "id": "55555555-6666-7777-8888-999999999999", "appId": "11111111-2222-3333-4444-555555555555", "appDisplayName": "<client-app-name>-Web", "displayName": "<client-app-name>-Web" } } } } The above payload was captured using browser-based authentication (native auth is not used), with the below parameters passed (identifiers, tenant name etc. redacted, otherwise intact): https://example.ciamlogin.com/ aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee/oauth2/v2.0/authorize ?response_type=code &client_id=11111111-2222-3333-4444-555555555555 &redirect_uri=https%3A%2F%2Fexample.com%2Fsignin%2Fcallback%2F &scope=openid+profile+email &state=<REDACTED> &prompt=login &ui_locales=de-DE &mkt=de-DE &nonce=<REDACTED> &code_challenge=<REDACTED> &code_challenge_method=S256 Following having navigated to the authorize endpoint above, the issue can be reproduced by entering an email address or an existing user identity, then on the password entry view, press the “Forgot Password?” link under the password input field, and then press the button/element “Email code to <user-email>”. I have looked at using the requestType in the email OTP send event payload to determine which email template and email content are used as per client requirement, but noted that the requestType seemingly always contains the value "signIn" even if the OTP code was sent as part of a password reset operation. At first glance, it would seem like this property indicates which step in the UI the user is currently at, even though I’m not certain whether that is what the property is actually meant to represent or indicate or not. However, for the above scenario and requirement, some identifier or value indicating the action would be needed in order to tailor the email content. The alternatives to having a reliable context property in the payload to indicate user action would require more or less significant additional components and infrastructure, thus increasing the complexity of the solution. Based on its name and values, it would seem like the requestType property appears be a good candidate to carry a user action context identifier. A suitable alternative solution has been adopted currently, using a generalized OTP template, which works well, but the requirement that it would be preferable to tailor the content based on user context and intent, e.g., whether the request was triggered as part of a password reset action or for another authentication scenario, is still present, ideally via the event payload sent from Entra External ID to the auth extension. If there would be any further/follow-up questions on the above, e.g., to clarify the requirement, or further explain the reproduction steps and behaviour observed, or anything else, please tell, and I'll ensure to get back as soon as possible. Also, would someone have some input on potential other/additional ways to make the requestType include a context identifier, that would be much appreciated as well, thanks! Regards Kristoffer
Locked account due to many attempts from malicious IP
Hello experts, today, a user contacted me that she cannot access M365 and asked to unlock her account. 1st thing I've checked were her log-ins in MS Entra and there I've found many and many attempts to log in from different countries - like India, Russia, Demark etc... that happened with just few seconds delay.... As a result, the user's account got blocked. Had to deal 1st time with this kind of issue.... See pictures below. Now, it looks like there was another user under the same attack few days ago (who is on vacation so doesnt know he is blocked for now :)).... Anyway, wondering - how I can prevent these types of attack? We have MFA (app auth) configured so even if the password got broken, MFA should prevent the attacker to sign in. I was going to create a conditional access but there are countries like Italy, Denmark (and other EU ones) etc that I don't want to block. We have M365 E3 with M365 E5 Security subscriptions assigned to all users. Would be grateful for any advise.Guest accounts and MFA via Conditional Access in MS Entra
Hi experts, trying to get some help on my scenario and issue that external users started to experience since I've enabled MFA for external identities & guest users via Conditional Access. We have lots of external partners that we share some documentation with from our SharePoint. Some time ago, I have enabled "MS Entra B2B Integration for SharePoint and OneDrive" so that any external user that access shared files/folders in our SharePoint gets a GUEST account created in our tenant. This was also preparation for enabling MFA for External users via Conditional Access. I believe these are called "B2B Collaboration guests" Now, few days ago, I have enabled MFA via Conditional Access for all external users and guests, enabled for all cloud apps and require MFA to grant access. Until now, I got feedback from two external partners that their existing access doesnt work anymore - and they need to go through MFA (which is expected). The problem is that when they go through MFA set up, it ends up in a "loop" - meaning, they go through all steps but when completing the last step they are returned back to the very 1st step again. So they: scan QR code successfully authenticate get the page that it was successful get back to the 1st step asking to install or use MS Auth app The user tried different browsers also with Incognito tabs... When I am checking sing-in logs: guest account is created fine the status is: "Interrupted" additional details: The user was presented options to provide contact options so that they can do MFA. conditional access forcing MFA is marked as FAILED as MFA was not completed Both external partners that reported this are using MS Entra and I see their IDENTITY as ExternalAzureAD. Have not heard back from anyone else using other than ExternalAzureAD so not sure if there is something extra that needs to be configured. Anyone experienced this issue? Any idea what can be wrong? I do not have any cross-tenant collaboration etc configured...Unexpected button behaviour when using the prompt=create parameter in Entra External ID user flows
Hi, In a recent workload, I'm assisting a client to implement Entra External ID for streamlined authorization as well as single sign-on for associated registered external facing third-party applications for external customer users through their Entra External ID identity, as well as assisting the client with auth branding and other UI customizations, and preparing Entra ID federation custom OIDC providers and configuration for enabling SSO with organizational internal and remote work- and school accounts etc. The sign-up / create account experience is of importance to the client, as a rather substantial amount of users are expected to sign-up via self-service sign-up following having received an invite via another app. To ensure that the user lands on the create account view, in order to minimize the number of steps and actions the users need to take to get there, the prompt=create parameter is used to pre-select the sign-up/register experience in the user flows UI. Having stress-tested the user flows and experience recently, we noticed that in a specific scenario, some UI elements behave in a manner that could be described as unexpected, and even though a workaround has mitigated it to some extent, the behaviour of some elements could probably be improved a bit to ensure an even more consistent user experience in the built-in user flows. Specifically, if the user flow is invoked with the prompt parameter set, the user lands on the create account screen as expected, however, unless custom CSS modification is applied, the Back button that would typically be there, as if having arrived there from the initial sign-in screen where it’s also displayed. If pressing the Back button displayed on the Create account view when having navigated there with the prompt=create set in the /authorize request, pressing the button seemingly doesn’t have any impact or result in any action, one can click it, but nothing happens. I'd suspect it's perhaps a "remnant" from if the flow is invoked without any prompt parameter set, or with prompt=login set, but when prompt=create is set, there is no state/page history in the UI to navigate back to, as no previous page has been displayed or rendered yet and added to the history, and the Back button click thus doesn’t have any effect. In general, I think buttons that don't have any tangible action should not be displayed, also, if prompt=login is set, the Back button isn't shown then either on the very initial user flow view shown then, so it would seem the built-in user flows actually already follow such approach in fact, but not when the prompt=create has been set, thus causing some inconsistency in the UI that users could notice unless custom CSS styling is applied. The expected behaviour for our business case would be that if prompt=create is set, then, similar to the prompt=login, no Back button should be displayed, or, if shown, it should result in some navigation (perhaps something like javascript.go(-1), but that could/would be dependent on from where the user arrived, e.g., going back a step in the browser history won't work if the user clicked a link from an invite email ) and preferably not be non-actionable. Furthermore, on the topic of the Back button and its behaviour when the prompt=create parameter is set, there is another case at which we observed some unexpected button behaviour as well, that could probably benefit from some attention. At a specific second scenario, it seems that the Continue button is displayed without providing any action, and when clicking the Back button then, clicking it seemingly resets the "create account", state likely set by the prompt=create initially, and instead switches the flow back to the sign-in state, which can at least affect the display text of some subsequent buttons shown in later steps in the UI. The user arrives at a built-in Entra External ID user flow /authorize endpoint, with the prompt=create query parameter set The user triggers the OTP challenge by entering an email address to verify the email address The user receives the OTP code but enters it incorrectly, i.e., doesn't copy the full code length of eight digits, and instead enters/pastes six of the eight code digits. The UI then shows an error message that the code could not be used/validated, and the email address field is displayed again with the email address that was used for the verification attempt prefilled. If the user clicks the Continue button at this stage, nothing happens. If the user clicks the Back button instead (given that it’s not hidden), it shows the same view one more time, with the Back and Continue buttons at the bottom. However, if the user clicks the Continue button this time, it works and a new code is sent. On the next screen, where the newly sent code can be entered, instead of a button named "Continue", it will now instead show a button with the text "Sign-in" (it would seem like the create account state has gotten lost somewhere along the way at this point, perhaps when the back button in the step 5 above was pressed). If one omits the prompt=create parameter, or when using prompt=login, things seem to work fine, the above occurs when the prompt=create is set. The reason why is the prompt=create is used is due to a business requirement to try to minimize the steps, especially in conjunction with the registration/sign-up, as far a possible when signing up. We have opted for the built-in user flows, not the self-hosted native authentication UI pages, for this project, and then as I understand it, it is the prompt=create parameter that can/should be used to enable the user to land directly on the registration page without having to navigate there manually via the sign-up link, that is otherwise shown on the initial sign-in page. It would thus be great if the prompt=create parameter could have some attention (or perhaps if a dedicated sign-up user flow type could be added potentially, even though that would perhaps warrant some update to the user flow app linking as well, as my understanding is that one user flow can be linked to one app registration at a time currently) to avoid that some buttons become unresponsive when the parameter is used, or falls back to sign-in, to improve the built-in user flows further, as the prompt=create fulfils the business requirement well otherwise. If there would be any further/follow-up questions on the above, e.g., to clarify the requirement, or further explain the reproduction steps and behaviour observed, or anything else, please tell, and I'll ensure to get back as soon as possible. Also, would someone have some input on potential other/additional ways to pre-select the create account/sign-up experience, that would naturally be much appreciated as well, thanks! Regards KristofferAuthentication Context (Entra ID) Use case
Microsoft Entra ID has evolved rapidly over the last few years, with Microsoft continuously introducing new identity, access, and security capabilities as part of the broader Zero Trust strategy. While many organizations hold the necessary Entra ID and Microsoft 365 licenses (often through E3 or E5 bundles), a number of these advanced features remain under‑utilised or entirely unused. This is frequently due to limited awareness, overlapping capabilities or uncertainty about where and how these features provide real architectural value. One such capability which is not frequently used is Authentication Context. Although this feature is available for quite some time, it is often misunderstood or overlooked because it does not behave like traditional Conditional Access controls. Consider Authentication Context as a mobile “assurance tag” that connects a resource (or a particular access route to that resource) to one or several Conditional Access (CA) policies, allowing security measures to be enforced with resource-specific accuracy instead of broad, application-wide controls. Put simply, it permits step-up authentication only when users access sensitive information or perform critical actions, while maintaining a smooth experience for the “regular path.” When used intentionally, it enables resource‑level and scenario‑driven access control, allowing organizations to apply stronger authentication only where it is actually needed without increasing friction across the entire user experience. Not expensive Most importantly to use Authentication Context the minimum licensing requirement is Microsoft Entra ID Premium P1 which most customers already have this license. so you not need to convenience for higher license to utilize this feature. But do note Entra Premium 2 is needed if your Conditional Access policy uses advanced signals, such as: User or sign‑in risk (Identity Protection) Privileged Identity Management (PIM) protected roles Risk‑based Conditional Access policies The Workflow Architecturally, Authentication Context works when a claims request is made as part of token issuance commonly expressed via the acrs claim. When the request includes a specific context (for example c1), Entra evaluates CA policies that target that context and forces the required controls (MFA, device compliance, trusted location, etc.). The important constraint: the context must be requested/triggered by a supported workload (e.g., SharePoint) or by an application designed to request the claim; it is not an automatic “detect any action inside any app” feature. Lets look at few high level architecture reference 1. Define “assurance tiers” as contexts Create a small set of contexts (e.g., c1: Confidential Access, c2: Privileged Operations) and publish them for use by supported apps/services. 2. Bind contexts to resources Assign the context to the resource boundary you want to protect—most commonly SharePoint sites (directly or via sensitivity labels), so only those sites trigger the context. (e.g - Specific SharePoint sites like financials, agreements etc ) 3. Attach Conditional Access policies to the context Create CA policies that target the context and define enforcement requirements (Additional MFA strength, mandating device compliance, or location constraint through named locations etc.). The context is the “switch” that activates those policies at the right moment. 4. Validate runtime behavior and app compatibility Because authentication context can impact some client apps and flows, validate supported clients and known limitations (especially for SharePoint/OneDrive/Teams integrations). Some Practical Business Scenarios Scenario A — Confidential SharePoint Sites (M&A / Legal / HR) Problem: You want stronger controls for a subset of SharePoint sites without forcing those controls for all SharePoint access. Architect pattern: Tag the confidential site(s) with Authentication Context and apply a CA policy requiring stronger auth (e.g., compliant device + MFA) for that context. Pre-reqs: SharePoint Online support for authentication context; appropriate licensing and admin permissions; CA policies targeted to the context Scenario B — “Step-up” Inside a Custom Line-of-Business App Problem: Users can access the app normally, but certain operations (approval, export, privileged view) need elevated assurance. Architect pattern: Build the app on OpenID Connect/OAuth2 and explicitly request the authentication context (via acrs) when the user reaches the sensitive path; CA then enforces step-up. Pre-reqs: App integrated with Microsoft identity platform using OIDC/OAuth2; the app can trigger claims requests/handle claim challenges where applicable; CA policies defined for the context Scenario C — Granular “Resource-based” Zero Trust Without Blanket MFA Problem: Security wants strong controls on crown jewels, but business wants minimal prompts for routine work. Architect pattern: Use authentication context to enforce higher assurance only for protected resources (e.g., sensitive SharePoint sites). This provides least privilege at the resource boundary while reducing global friction. Pre-reqs: Clearly defined resource classification; authentication context configured and published; CA policies and monitoring. In a nutshell, Authentication Context allows organizations to move beyond broad, one‑size‑fits‑all Conditional Access policies and adopt a more precise, resource‑driven security model. By using it to link sensitive resources or protected access paths to stronger authentication requirements, organizations can improve security outcomes while minimizing unnecessary user friction. When applied deliberately and aligned to business‑critical assets, Authentication Context helps close the gap between licensing capability and real‑world value—turning underused Entra ID features into practical, scalable Zero Trust controls. If you find this useful, please do not forget to like and add your thoughts 🙂
Can the built-in "No account? Create one" link redirect to a custom sign-up page?
I'm using Microsoft Entra External ID with a built-in sign-in/sign-up user flow. On the Microsoft-hosted sign-in page, the "No account? Create one" link always redirects users to the default Entra sign-up page. I already have a custom registration page and would like this built-in link to redirect to my custom URL instead. Is there any supported way to customize the destination of this link in a built-in user flow? If not, could someone confirm whether this behavior is fixed by design? Thanks!
Orphaned TPM-bound Entra Workplace Join device — no tenant access, backend deletion required
I have a personal Windows device that remains stuck in a TPM-protected Workplace Join to a former Microsoft Entra ID tenant. I no longer have tenant access and am not an admin. Local remediation completed: - dsregcmd /leave executed as SYSTEM - All MS-Organization / AAD certificates removed - Device still reports WorkplaceJoined : YES Azure Support ticket creation fails with: AADSTS160021 – interaction_required Application requested a user session which does not exist. Tenant inaccessible / user not present in tenant. This is an orphaned Entra ID device object. Requesting guidance or escalation for backend deletion. Tenant ID: 99f9b903-8447-4711-a2df-c5bd1ad1adf7 Device ID: f47987f4-a20b-4c34-a5f7-40ab0f593c6c
MFA Options for Employees without Phones
Hello everbody, we're currently trying to implement MFA in our company, but approximately 1/10 of our employees have a workphone and are not allowed to use their personal phone. Since we also recently introduced Intune, the idea was to just use Windows Hello for Business, but when trying to provision it, we realized that you need to have MFA active for an account to be able to even activate it? Which kinda defeats the purpose. So my question is, is there some way to circumvent the MFA requirement for WHfB? Or what other options do we realistically have? Thanks in Advance!
