Authentication 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 🙂
MFA catch-22 during onboarding due to registration policy
Hi, We are experiencing a catch-22 scenario during user onboarding related to MFA. New users are required to install the Microsoft Authenticator app via our Company Portal. However, they are prompted to complete MFA registration before they can access or download anything from the Company Portal. Since they do not yet have the Authenticator app installed, they are effectively blocked from completing the MFA setup. From our investigation, it appears that the Multi-Factor Authentication registration policy is enforcing MFA registration for new users. In our scenario, this creates a circular dependency. We have attempted to exclude our office network from MFA using Conditional Access, but this does not resolve the issue because the MFA registration policy is triggered before Conditional Access policies are evaluated. Our questions: Is there a recommended way to handle MFA onboarding in this type of scenario? Can Conditional Access policies be used instead of the MFA registration policy for initial MFA enrollment?
Free Webinar: Microsoft Entra ID Break-Glass Accounts Done Right (Live Demo + Q&A)
Hi everyone, I’m hosting a free community webinar focused on one of the most common (and painful) Entra ID issues: tenant lockouts caused by break-glass account misconfiguration. This session is practical and demo-driven, and I’ll cover real-world scenarios I’ve seen involving Conditional Access and emergency access design. What we’ll cover Why every tenant should have at least two break-glass accounts Common misconfigurations that lead to lockouts Conditional Access exclusions: what works and what fails Recommended hardening approach (without blocking emergency access) Monitoring + alerting best practices Live demo + Q&A Who it’s for Microsoft 365 admins Entra ID / Conditional Access admins Security engineers MSP engineers The recording will be shared with registrants after the session. Registration link: https://teams.microsoft.com/l/meetup-join/19%3ameeting_MjkwYzExNzItMzY4OC00NThmLTg2ZDYtM2ExMTRiNWYwMGZl%40thread.v2/0?context=%7b%22Tid%22%3a%224bb6dd74-2dd1-459b-b867-f51781e1e7ed%22%2c%22Oid%22%3a%2251c6a848-6393-44f9-bac5-21855d5c7c3d%22%7d Thanks! Jaspreet Singh
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
Entra Enterprise apps and App registrations - Global Secure Access - Conditional Access Block
I am working on a rollout for Global Secure Access and ran into an issue with Entra Enterprise apps setup in the tenant. With Global Secure Access I have a Conditional Access Policy set to Block access to All Resources excluding some resources like Intune and Defender tap required for mobile setup. When I added an administrator account which had done some Enterprise application setup and authorization for various third-party applications, those third-party applications stopped working with failed logins indicating token access issues. Upon review I found the majority of applications to be using client secret authentication with this administrator account as the authorizer. My limited knowledge of Enterprise apps leads me to believe this client secret is an application password that the third-party uses to keep generating tokens based on the authorizing account. My questions surrounding this setup and further understanding are mainly in relation to how Enterprise apps and app registrations authenticate, as well as user authentication directly. 1. How does the token authorization work? Does the application just use the client secret to authenticate as the user who authorized it to generate an access token? Why does MFA requirements and changing passwords not affect this but specific Block policy does? 2. What are best practices in relation to authorizing third-party applications? My thoughts are a dedicated account to authorize applications when needed. 3. How will this work with applications regular users use? Say a user has a digital notebook that syncs with their OneNote or a calendar app that syncs calendars between Outlook and their website. Do these applications also use client secrets with the user's token and will break when added to the GSA setup I have? Is the only way around this to authorize with an admin account for token issuance? Thank you for your time reading this and any insight you may have for any of the questions or ideas mentioned.
Fido passkeys blocked by policy
Hi all I'm helping out a customer with deploying physical passkeys and I'm running into a weird error. I've activated the sign in method and selected the two AAGuids for the Authenticator app and I've added the right AAGuid for the brand and model of passkey we are using. We can select the authentication method and enroll the security correctly but when trying to sign in using it we get the error as displayed in the attached picture. When checking the sign in logs i get this error message FIDO sign-in is disabled via policy and the error code is: 135016 I've not been able to track down any policy that would be blocking passkeys. anyone got any ideas?Grant Just-in-Time Admin Access with Microsoft Entra PIM
In my lab, I worked with Microsoft Entra Privileged Identity Management (PIM) to grant Just-in-Time admin access. Instead of permanent assignments, users become eligible for roles and must activate them only when needed. Steps I tested: - Configured roles as eligible rather than permanent - Required MFA and approval for role activation - Verified access automatically expired after the time window This approach reduces standing privileges and aligns with Zero Trust by securing privileged access. Curious — does your org still keep permanent Global Admins, or have you moved to JIT with PIM?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.Global Secure Access - Conditional Access Require GSA - Android Blocked
Hello all, I am currently working on deploying Global Secure Access client with Microsoft Forward Traffic profile and a conditional access policy to block access to M365 services unless connected through the GSA client. I have this working as I want it for Windows and mobile devices in a tenant we use for development. However, when I set this up at our live tenant, I cannot get the Android device to work. My setup is a Personally Owned Work Profile with the Defender app deployed and configured to enable GSA. I can connect to Global Secure Access and it does show some traffic tunneling to Microsoft. However, when I go to login to another app like Outlook, it blocks the sign-in. This is not the case for an iPhone I have personally enrolled and my Entra Joined laptop. Upon investigation of any differences between our development tenant (working fully) and our tenant (Android not working) I found that in the GSA section under Services, there is an extra service called “Microsoft Entra Channel Access”. This service does not show up when I am logged in our developer tenant. Even on the same phone by removing work profiles and signing in to both tenants, our live tenant shows the new channel, and the developer tenant does not have it. I did some log review with the advanced diagnostics feature and the app and noted a few things I am lead to believe that the issue is with this new Entra Channel that has been deployed to our live tenant and not to our dev tenant yet. When I go to sign-in to the Outlook application in the work profile for the developer tenant, I can see the authentication traffic being tunneled through the Microsoft 365 profile. (login.live.com, login.microsoftonline.com, and aadcdn.msftauth.net). However, in our production tenant when doing the same test I do not see those destinations being tunneled at all. I do see the traffic being collected in the “Hostname” section, but is not being tunneled. Another interesting point with this is that on an iPhone I am testing; I do see the authentication destinations being tunneled through the Entra Channel. Here are the screenshots of my findings. https://imgur.com/a/82r3HQC I have an open Microsoft support case and hoping to get the attention of a Microsoft employee or MVP who may be able to get this in front of the Entra product team to see if this is a bug.
Block all 365 apps except Outlook via CA
Trying to block 365 for a subset of users, except email. The old app-based CA rules made this easy. The new 'resource' based setup... I'm not even sure if it's possible. CoPilot just keeps telling me to use the old version of CA, because it hasn't clued into Microsoft's downgrade cycle. If I try to filter by resource attribute, I'm told I don't have permission to do so. I'm the global admin. Here's what searching for Outlook gives me and Exchange Advice? We ARE intune licensed, but i'm not sure App Protection Policies will help here. The intention is to block BYOD from accessing anything but Outlook / Exchange. That is, Mobile devices that aren't (whatever param I decide on)
