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?
Nested App Authentication (NAA) token to protect middle-tier server
I'm working on an outlook addin and want to use the NAA accesstoken to validate the user on an api running on a php webserver. The addin runs as a taskepane (created with yo office) with the app only manifest. I have setup NAA to do Microsoft graph calls on behalf of the user. I have used this guid to setup NAA (copy/past) https://learn.microsoft.com/en-us/office/dev/add-ins/develop/enable-nested-app-authentication-in-your-add-in I have setup a php server (not in Microsoft infrastruktur) for a simple API, that handlers MySQL calls and app only calls to Microsoft graph. The php api authenticate itself with a client secret from the Azure app registration. Both are working as expected. Can i use the accesstoken from the NAA, to authenticate the user on the php server? If it can be done how do I validate the token?
Multi-Factor Authentication for people without a Smart Phone?
Howdy, We have a couple people who don't have Smart Phones and need to use MFA. We don't want to use a simple Text Message if we can and prefer to use something a bit more secure. I found there is an Authenticator App for Windows 10 but it doesn't seem to work with O365 accounts. Are there any sort of keyfob dongle or USB dongle thing that work with Office 365 that we can get for people who don't have smartphones? I've used the kind where the number on the fob changes every minute just like an authenticator app would but that was many years ago. If anyone knows something we can use to make this work, let me know. Thanks!
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?External people can't open files with Sensitivity Label encryption.
Question: What are the best practices for ensuring external users can open files encrypted with Sensitivity Labels? Hi all. I've been investigating proper setup of sensitivity labels in Purview, and the impact on user experience. The prerequisites are simple enough, creating and configuring the labels reasonably straightforward, and publishing them is a breeze. But using them appears to be a different matter! Everything is fine for labels that don't apply encryption (control access) or when used internally. However, the problems come when labels do apply encryption and information is sent externally. The result is that we apply a label to a document, attach that document to an email, and send it externally - and the recipient says they can't open it and they get an error that their email address is not in our directory. This is because due to the encryption, the external user needs to authenticate back to our tenant, and if they're not in our tenant they obviously can't do this so the files won't open. So, back to the question above. What's the easiest / most secure / best way to add any user we might share encrypted content with to our tenant. As I see it we have the following options: Users have to request Admins add the user as a Guest in our tenant before they send the content. Let's face it, they'll not do this and/or get frustrated. Users share encrypted content directly from SharePoint / OneDrive, rather than attaching it to emails (as that would automatically add the external person as a Guest in the tenant). This will be fine in some circumstances, but won't always be appropriate (when you want to send them a point-in-time version of a doc). With good SharePoint setup, site Owners would also have to approve the share before it gets sent which could delay things. Admins add all possible domains that encrypted content might be shared with to Entra B2B Direct Connect (so the external recipient doesn't have to be our tenant). This may not be practical as you often don't know who you'll need to share with and we work with hundreds of organisations. The bigger gotcha is that the external organisation would also have to configure Entra B2B Direct Connect. Admins default Entra B2B Direct Connect to 'Allow All'. This opens up a significant attack surface and also still requires any external organisation to configure Entra B2B Direct Connect as well. I really want to make this work, but it need to be as simple as possible for the end users sharing sensitive or confidential content. And all of the above options seem to have significant down-sides. I'm really hoping someone who uses Sensitivity Labels on a day-to-day basis can provide some help or advice to share their experiences. Thanks, Oz.Escalation Inquiry: IP Logs Request for MS Account
Hello, I am seeking advice regarding a security issue with my Microsoft account. There were unauthorized login attempts on my account between May 23 and May 25, 2025. I submitted a ticket to Microsoft Privacy / Security Incident Response (SIR) regarding IP activity logs. My ticket was created on August 7, 2025 and escalated to the IP/SIR team on August 11, 2025. Since then, I have sent multiple follow-ups, but no response has been received. I also created a new ticket on September 17, 2025, but only received the automatic acknowledgment; no agent has contacted me. I am concerned because the logs are important for verifying my account security and ensuring no unauthorized access occurred. Could anyone advise typical processing times for IP activity requests or suggest ways to escalate this issue effectively? Thank you in advance for any guidance.Azure AD Health Failing
I am on the latest version of Azure AD Connect (2.5.79.0)... There are no network/DNS/connectivity issues at our site, it seems to me that Azure AD Health Service is having trouble because the endpoint is experiencing a service issue.. Is anyone else having the same problem with failure alerts/etc? I checked by running "Test-MicrosoftEntraConnectHealthConnectivity -Role SYNC" command, the stack trace throws an undocumented error number and complains of rate limiting issues... smells like the server is being overwhelmed or there are other issues slowing down the endpoint/service with the consequence that connections are piling up causing this error: Connectivity Test Step 1 of 2: Testing dependent service endpoints begins ... AAD CDN connectivity is skipped. Connecting to endpoint https://login.microsoftonline.com Endpoint validation for https://login.microsoftonline.com is Successful. Connecting to endpoint https://s1.adhybridhealth.azure.com/providers/Microsoft.ADHybridHealthService/diagnostics/version Endpoint validation for https://s1.adhybridhealth.azure.com/providers/Microsoft.ADHybridHealthService/diagnostics/version is Successful. Connectivity Test Step 1 of 2 - Testing dependent service endpoints completed successfully. Connectivity Test Step 2 of 2 - EventHub data upload procedure begins ... Tenant Id is successfully collected during agent registration. Server rejected Eventhub data upload, here is the exception: Microsoft.ServiceBus.Messaging.ServerBusyException: The request was terminated because the entity is being throttled. Error code : 50002. Sub error : 101. Please wait 4 seconds and try again. To know more visit https://aka.ms/sbResourceMgrExceptions and https://aka.ms/ServiceBusThrottlingS:N:ADHSPRODWUSEHSYNCIA:EVENTHUB:ADHSPRODWUSEHSYNCIA~22527,CL:30,CC:32,ACC:356250,LUR:WinEnd,LUT:2025-10-08T03:03:12.2035867Z,RC:1 TrackingId:<<< anonymized tracking ID>>> 0, SystemTracker:adhsprodwusehsyncia:eventhub:adhsprodwusehsyncia~22527, Timestamp:2025-10-08T03:03:13 at Microsoft.ServiceBus.Common.ExceptionExtensions.ThrowException(Exception exception) at Microsoft.ServiceBus.Common.AsyncResult.End[TAsyncResult](IAsyncResult result) at Microsoft.ServiceBus.Messaging.EventHubSender.Send(EventData data) at Microsoft.Identity.Health.AgentV1.ConfigurationPowerShell.TestAzureADConnectHealthConnectivity.TestInsightServiceDataUploadProcedure() Azure AD Connect Health agent could not communicate to the Health Service using port 5671. As a result, agent communication will fall back to use port 443, but use of port 5671 is recommended. Please allow outbound communication using port 5671. Tenant Id is successfully collected during agent registration. Server rejected Eventhub data upload, here is the exception: Microsoft.ServiceBus.Messaging.ServerBusyException: The request was terminated because the entity is being throttled. Error code : 50002. Sub error : 101. Please wait 4 seconds and try again. To know more visit https://aka.ms/sbResourceMgrExceptions and https://aka.ms/ServiceBusThrottlingS:N:ADHSPRODWUSEHSYNCIA:EVENTHUB:ADHSPRODWUSEHSYNCIA~22527,CL:30,CC:32,ACC:356837,LUR:IncomingUsage_ADHSPRODWUSEHSYNCIA-5,LUT:2025-10-08T03:03:54.9448143Z,RC:1 TrackingId:<<< anonymized tracking ID>>>, SystemTracker:adhsprodwusehsyncia:eventhub:adhsprodwusehsyncia~22527, Timestamp:2025-10-08T03:04:00 at Microsoft.ServiceBus.Common.ExceptionExtensions.ThrowException(Exception exception) at Microsoft.ServiceBus.Common.AsyncResult.End[TAsyncResult](IAsyncResult result) at Microsoft.ServiceBus.Messaging.EventHubSender.Send(EventData data) at Microsoft.Identity.Health.AgentV1.ConfigurationPowerShell.TestAzureADConnectHealthConnectivity.TestInsightServiceDataUploadProcedure() Azure AD Connect Health agent could not communicate to the Health Service using port 5671. As a result, agent communication will fall back to use port 443, but use of port 5671 is recommended. Please allow outbound communication using port 5671.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.
