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.Request to enable preview feature - Face Check with CAP
Dear Microsoft, I am on a business premium plan for my home test tenant. I cannot raise ticket nor do I have an account manager. I know this is in private preview. I would like my tenant to be enabled to test this new Verified ID feature to have "Face Check" in CAP as one of the Grant conditions. tenant id: bc85b508-0107-4472-a49c-fc8cefd4f0d7 Thank you.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.Does Rights Management Service currently support MFA claims from EAM?
We've been testing EAM (external authentication methods) for a few months now as we try to move our Duo configuration away from CA custom controls. I noticed today that when my Outlook (classic) client would not correctly authenticate to Rights Management Service to decrypt OME-protected emails from another org. It tries to open the message, fails to connect to RMS, and opens a copy of the email with the "click here to read the message" spiel. It then throws a "something is wrong with your account" warning in the Outlook client's top right corner. If I try to manually authenticate & let it redirect to Duo's EAM endpoint, it simply fails with an HTTP 400 error. When you close that error, it then presents another error of "No Network Connection. Please check your network settings and try again. [2603]". I can close/reopen Outlook and that warning message in the top right stays suppresses unless I attempt signing into RMS all over again. However.. If I do the same thing and instead use an alternate MFA method (MS Authenticator, for example), it signs in perfectly fine and will decrypt those OME-protected emails on the fly in the Outlook client, as expected. I verified that we excluded "aadrm.com" from SSL inspection and that we're not breaking certificate pinning. So all I can assume at the moment is that Rights Management Service isn't honoring MFA claims from EAM. Any experience/thoughts on this? Thanks in advance!"sign-in frequency" every time not working as expected and described.
We have several PIM managed groups in an Entra ID tenant. Members are added as eligible. For the activation of the memberships an Authentication Context is created which is linked to a conditional access policy. The conditional access policy requires MFA with phishing resistant authentication factors, and "sign in frequency" is set to "every time". When activating membership authentication is required. When activating membership to another group (>5min in between activations) one would expect to request an authentication prompt, as described in Microsoft documentation. In Firefox this works as expected, In Edge and Chrome there is no re-authentication required every time, and sometimes even not for the first activation, not even in an in-private session. The device is not joined to this tenant, and the account used to log on is different from the one used to logon to the Entra ID portal. This is a test tenant with only those CA rules configured, no other policies or rules are in place. Anyone experiencing the same, or knowing the cause?
Can External ID (CIAM) federate to an Azure AD/Entra ID tenant using SAML?
What I'm trying to achieve I'm setting up SAML federation FROM my External ID tenant (CIAM) TO a partner's Entra ID tenant (regular organizational tenant) for a hybrid CIAM/B2B setup where: Business users authenticate via their corporate accounts (OIDC or SAML) Individual customers use username/password or social providers (OIDC) Tenant details / Terminology: CIAM tenant: External ID tenant for customer-facing applications IdP tenant: Example Partner's organizational Entra ID tenant with business accounts Custom domain: mycustomdomain.com (example domain for the IdP tenant) Configuration steps taken Step 1: IdP Tenant (Entra ID) - Created SAML App Set up Enterprise App with SAML SSO Entity ID: https://login.microsoftonline.com/<CIAM_TENANT_ID>/ Reply URL: https://<CIAM_TENANT_ID>.ciamlogin.com/login.srf NameID: Persistent format Claim mapping: emailaddress → user.mail Step 2: CIAM Tenant (External ID) - Added SAML IdP (Initially imported from the SAML metadata URL from the above setup) Federating domain: mycustomdomain.com Issuer URI: https://sts.windows.net/<IDP_TENANT_ID>/ Passive endpoint: https://login.microsoftonline.com/mycustomdomain.com/saml2 DNS TXT record added: DirectFedAuthUrl=https://login.microsoftonline.com/mycustomdomain.com/saml2 Step 3: Attached to User Flow Added SAML IdP to user flow under "Other identity providers" Saved configuration and waited for propagation The problem It doesn't work. When testing via "Run user flow": No SAML button appears (should display "Sign in with mycustomdomain") Entering email address removed for privacy reasons doesn't trigger federation The SAML provider appears configured but never shows up in the actual flow Also tried using the tenant GUID in the passive endpoint instead of the domain - same result My question Is SAML federation from External ID to regular Entra ID tenants actually possible? I know OIDC federation to Microsoft tenants is (currently, august 2025) explicitly blocked (microsoftonline.com domains are rejected). Is SAML similarly restricted? The portal lets me configure everything without throwing any errors, but it never actually works. Am I missing something in my configuration? The documentation for this use case is limited and I've had to piece together the setup from various sources. Or is this a fundamental limitation where External ID simply can't federate to ANY Microsoft tenant regardless of the protocol used?Windows Live Custom Domains causes Entra account lockout
Hi everyone, we have an on-prem AD connected with EntraConnect to EntraID since about 3 years. We only sync users and groups, no password hash or anything else. Since a few days 4 (out of about 250) users are constantly being locked out due to failed login attempts on an Application called "Windows Live Custom Domains". All 4 users are locked out not at the same time but within 30 min to an hour. This happens multiple times a day. As far as I was able to investigate Windows Live Custom Domains is a service no longer offered by MS or has been replaced with something else. How am I able to find out where this failed login attempts come from? If someone could point me in the right direction I would be very happy. Thanks DanielUsing Entra ID Authentication with Arc-Enabled SQL Server in a .NET Windows Forms Application
Introduction: This guide demonstrates how to securely connect a .NET Framework Windows Forms application to an Arc-enabled SQL Server 2022 instance using Entra ID (Azure AD) authentication. It covers user authentication, token management, and secure connection practices, with code samples and screenshots. In many modern applications, it is common practice to use an application web service to mediate access to SQL Server. This approach can offer several advantages, such as improved security, scalability, and centralized management of database connections. However, there are scenarios where directly connecting to SQL Server is more appropriate. This guide focuses on such scenarios, providing a solution for applications that need direct access to SQL Server. This model is particularly useful for applications like SQL Server Management Studio (SSMS), which require direct database connections to perform their functions. By using Entra ID authentication, we can ensure that these direct connections are secure and that user credentials are managed efficiently. By following the steps outlined in this guide, developers can ensure secure and efficient connections between their .NET Windows Forms applications and Arc-enabled SQL Server instances using Entra ID authentication. This approach not only enhances security but also simplifies the management of user credentials and access tokens, providing a robust solution for modern application development. SAMPLE CODE: GitHub Repository Prerequisites Arc-enabled SQL Server 2022/2025 configured for Entra ID authentication Entra ID (Azure AD) tenant and app registration .NET Framework 4.6.2 Windows Forms application (Not required .NET version, only what the solution is based on) Microsoft.Identity.Client, Microsoft.Data.SqlClient NuGet packages Application Overview User authenticates with Entra ID Token is acquired and used to connect to SQL Server Option to persist token cache or keep it in memory Data is retrieved and displayed in a DataGridView Similar setup to use SSMS with Entra ID in articles below. Windows Form Sample Check User Button shows the current user The Connect to Entra ID at Login button will verify if you are logged in and try to connect to SQL Server. If the user is not logged in, an Entra ID authentication window will be displayed or ask you to log in. Once logged in it shows a Connection successful message box stating the connection to the database was completed. The Load Data button queries the Adventure Works database Person table and loads the names into the datagridview. The Cache Token to Disk checkbox option either caches to memory when unchecked and would require reauthentication after the application closes, or the option to cache to disk the token to be read on future application usage. If the file is cached to disk, the location of the cached file is (C:\Users\[useraccount]\AppData\Local). This sample does not encrypt the file which is something that would be recommended for production use. This code uses MSAL (Microsoft Authentication Library) to authenticate users in a .NET application using their Microsoft Entra ID (Azure AD) credentials. It configures the app with its client ID, tenant ID, redirect URI, and logging settings to enable secure token-based authentication. //Application registration ClientID, and TenantID are required for MSAL authentication private static IPublicClientApplication app = PublicClientApplicationBuilder.Create("YourApplicationClientID") .WithAuthority(AzureCloudInstance.AzurePublic, "YourTenantID") .WithRedirectUri("http://localhost") .WithLogging((level, message, containsPii) => Debug.WriteLine($"MSAL: {message}"), LogLevel.Verbose, true, true) .Build(); This method handles user login by either enabling persistent token caching or setting up temporary in-memory caching, depending on the input. It then attempts to silently acquire an access token for Azure SQL Database using cached credentials, falling back to interactive login if no account is found. private async Task<AuthenticationResult> LoginAsync(bool persistCache) { if (persistCache) TokenCacheHelper.EnablePersistence(app.UserTokenCache); else { app.UserTokenCache.SetBeforeAccess(args => { }); app.UserTokenCache.SetAfterAccess(args => { }); } string[] scopes = new[] { "https://database.windows.net//.default" }; var accounts = await app.GetAccountsAsync(); if (accounts == null || !accounts.Any()) return await app.AcquireTokenInteractive(scopes).ExecuteAsync(); var account = accounts.FirstOrDefault(); return await app.AcquireTokenSilent(scopes, account).ExecuteAsync(); } Connecting to SQL Server with Access Token This code connects to an Azure SQL Database using a connection string and an access token obtained through MSAL authentication. It securely opens the database connection by assigning the token to the SqlConnection object, enabling authenticated access without storing credentials in the connection string. This sample uses a self-signed certificate, in production always configure SQL Server protocols with a certificate issued by a trusted Certificate Authority (CA). TrustServerCertificate=True bypasses certificate validation and can allow MITM attacks. For production, use a trusted Certificate Authority and change TrustServerCertificate=True to TrustServerCertificate=False. Configure Client Computer and Application for Encryption - SQL Server | Microsoft Learn string connectionString = $"Server={txtSqlServer.Text};Database=AdventureWorks2019;Encrypt=True;TrustServerCertificate=True;"; var result = await LoginAsync(checkBox1.Checked); using (var conn = new SqlConnection(connectionString)) { conn.AccessToken = result.AccessToken; conn.Open(); // ... use connection ... } Fetching Data into DataGridView This method authenticates the user and connects to an Azure SQL Database using an access token, and runs a SQL query to retrieve the top 1,000 names from the Person table. It loads the results into a DataTable, which can then be used for display or further processing in the application. private async Task<DataTable> FetchDataAsync() { var dataTable = new DataTable(); var result = await LoginAsync(checkBox1.Checked); using (var conn = new SqlConnection(connectionString)) { conn.AccessToken = result.AccessToken; await conn.OpenAsync(); using (var cmd = new SqlCommand("SELECT TOP (1000) [FirstName], [MiddleName], [LastName] FROM [AdventureWorks2019].[Person].[Person]", conn)) using (var reader = await cmd.ExecuteReaderAsync()) { dataTable.Load(reader); } } return dataTable; } Configure Azure Arc SQL Server to use Entra ID authentication Using SQL Server 2022 follow the instructions here to setup the key vault and certificate when configuring. This article can also be used to configure SSMS to use Entra ID authentication. Detailed steps located here: Set up Microsoft Entra authentication for SQL Server - SQL Server | Microsoft Learn Using SQL Server 2025 the setup is much easier as you do not need to configure a Key Vault, or certificates as it is relying on using the managed identity for the authentication. Entra ID App Registration Steps Register a new app in Azure AD Add a redirect URI (http://localhost) Add API permissions for https://database.windows.net/.default On the Entra ID app registration, click on API Permissions. Add the API’s for Microsoft Graph: User.Read.All Application.Read.All Group.Read.All Add a permission for Azure SQL Database. If Azure SQL database is not shown in the list ensure that the Resource Provider is registered for Microsoft.Sql. Choose Delegated permissions and select user_impersonation, Click Add permission for the Azure SQL Database. NOTE: Once the permissions are added ensure that you grant admin consent on the items. Security Considerations Never store client secrets in client apps Use in-memory token cache for higher security, or encrypted disk cache for convenience Use user tokens for auditing and least privilege References Microsoft Docs: Azure AD Authentication for SQL Server MSAL.NET Documentation Arc-enabled SQL Server Documentation Conclusion: By following the steps outlined in this guide, developers can ensure secure and efficient connections between their .NET Windows Forms applications and Arc-enabled SQL Server instances using Entra ID authentication. This approach not only enhances security but also simplifies the management of user credentials and access tokens, providing a robust solution for modern application development. *** Disclaimer *** The sample scripts are not supported under any Microsoft standard support program or service. The sample scripts are provided AS IS without warranty of any kind. Microsoft further disclaims all implied warranties including, without limitation, any implied warranties of merchantability or of fitness for a particular purpose. The entire risk arising out of the use or performance of the sample scripts and documentation remains with you. In no event shall Microsoft, its authors, or anyone else involved in the creation, production, or delivery of the scripts be liable for any damages whatsoever (including, without limitation, damages for loss of business profits, business interruption, loss of business information, or other pecuniary loss) arising out of the use of or inability to use the sample scripts or documentation, even if Microsoft has been advised of the possibility of such damages.
MFA breakglass account recommendations?
Hi folks. Looking at the new Authentication Methods settings, and trying to consider the scenario where someone disables all of these methods by accident. We require MFA on all accounts (using the 'require MFA' param of Conditional Access). If these are all disabled, there's no MFA method available... Trying to think of ways around this, for that situation. Things I've considered - cert based auth, telephone auth, etc - all require the corresponding auth method to be enabled. How should this be handled?
