[PM-27731] Updated organization licenses to save the correct values from the token

src/Core/AdminConsole/Models/Data/Organizations/SelfHostedOrganizationDetails.cs

@@ -128,6 +128,7 @@ public Organization ToOrganization()
             UseApi = UseApi,
             UseResetPassword = UseResetPassword,
             UseSecretsManager = UseSecretsManager,
+            UsePasswordManager = UsePasswordManager,
             SelfHost = SelfHost,
             UsersGetPremium = UsersGetPremium,
             UseCustomPermissions = UseCustomPermissions,
@@ -156,6 +157,8 @@ public Organization ToOrganization()
             UseAdminSponsoredFamilies = UseAdminSponsoredFamilies,
             UseDisableSmAdsForUsers = UseDisableSmAdsForUsers,
             UsePhishingBlocker = UsePhishingBlocker,
+            UseOrganizationDomains = UseOrganizationDomains,
+            UseAutomaticUserConfirmation = UseAutomaticUserConfirmation,
         };
     }
 }

src/Core/Billing/Organizations/Commands/UpdateOrganizationLicenseCommand.cs

@@ -1,9 +1,11 @@
 using System.Text.Json;
 using Bit.Core.AdminConsole.Entities;
+using Bit.Core.Billing.Enums;
 using Bit.Core.Billing.Licenses;
 using Bit.Core.Billing.Licenses.Extensions;
 using Bit.Core.Billing.Organizations.Models;
 using Bit.Core.Billing.Services;
+using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Models.Data.Organizations;
 using Bit.Core.Services;
@@ -46,6 +48,57 @@ public async Task UpdateLicenseAsync(SelfHostedOrganizationDetails selfHostedOrg
         }
 
         var claimsPrincipal = _licensingService.GetClaimsPrincipalFromLicense(license);
+
+        // If the license has a Token (claims-based), extract all properties from claims BEFORE validation
+        // This ensures that CanUseLicense validation has access to the correct values from claims
+        // Otherwise, fall back to using the properties already on the license object (backward compatibility)
+        if (claimsPrincipal != null)
+        {
+            license.Name = claimsPrincipal.GetValue<string>(OrganizationLicenseConstants.Name);
+            license.BillingEmail = claimsPrincipal.GetValue<string>(OrganizationLicenseConstants.BillingEmail);
+            license.BusinessName = claimsPrincipal.GetValue<string>(OrganizationLicenseConstants.BusinessName);
+            license.PlanType = claimsPrincipal.GetValue<PlanType>(OrganizationLicenseConstants.PlanType);
+            license.Seats = claimsPrincipal.GetValue<int?>(OrganizationLicenseConstants.Seats);
+            license.MaxCollections = claimsPrincipal.GetValue<short?>(OrganizationLicenseConstants.MaxCollections);
+            license.UsePolicies = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UsePolicies);
+            license.UseSso = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseSso);
+            license.UseKeyConnector = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseKeyConnector);
+            license.UseScim = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseScim);
+            license.UseGroups = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseGroups);
+            license.UseDirectory = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseDirectory);
+            license.UseEvents = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseEvents);
+            license.UseTotp = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseTotp);
+            license.Use2fa = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.Use2fa);
+            license.UseApi = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseApi);
+            license.UseResetPassword = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseResetPassword);
+            license.Plan = claimsPrincipal.GetValue<string>(OrganizationLicenseConstants.Plan);
+            license.SelfHost = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.SelfHost);
+            license.UsersGetPremium = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UsersGetPremium);
+            license.UseCustomPermissions = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseCustomPermissions);
+            license.Enabled = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.Enabled);
+            license.Expires = claimsPrincipal.GetValue<DateTime?>(OrganizationLicenseConstants.Expires);
+            license.LicenseKey = claimsPrincipal.GetValue<string>(OrganizationLicenseConstants.LicenseKey);
+            license.UsePasswordManager = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UsePasswordManager);
+            license.UseSecretsManager = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseSecretsManager);
+            license.SmSeats = claimsPrincipal.GetValue<int?>(OrganizationLicenseConstants.SmSeats);
+            license.SmServiceAccounts = claimsPrincipal.GetValue<int?>(OrganizationLicenseConstants.SmServiceAccounts);
+            license.UseRiskInsights = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseRiskInsights);
+            license.UseOrganizationDomains = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseOrganizationDomains);
+            license.UseAdminSponsoredFamilies = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseAdminSponsoredFamilies);
+            license.UseAutomaticUserConfirmation = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseAutomaticUserConfirmation);
+            license.UseDisableSmAdsForUsers = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UseDisableSmAdsForUsers);
+            license.UsePhishingBlocker = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.UsePhishingBlocker);
+            license.MaxStorageGb = claimsPrincipal.GetValue<short?>(OrganizationLicenseConstants.MaxStorageGb);
+            license.InstallationId = claimsPrincipal.GetValue<Guid>(OrganizationLicenseConstants.InstallationId);
+            license.LicenseType = claimsPrincipal.GetValue<LicenseType>(OrganizationLicenseConstants.LicenseType);
+            license.Issued = claimsPrincipal.GetValue<DateTime>(OrganizationLicenseConstants.Issued);
+            license.Refresh = claimsPrincipal.GetValue<DateTime?>(OrganizationLicenseConstants.Refresh);
+            license.ExpirationWithoutGracePeriod = claimsPrincipal.GetValue<DateTime?>(OrganizationLicenseConstants.ExpirationWithoutGracePeriod);
+            license.Trial = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.Trial);
+            license.LimitCollectionCreationDeletion = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.LimitCollectionCreationDeletion);
+            license.AllowAdminAccessToAllCollectionItems = claimsPrincipal.GetValue<bool>(OrganizationLicenseConstants.AllowAdminAccessToAllCollectionItems);
+        }
+
         var canUse = license.CanUse(_globalSettings, _licensingService, claimsPrincipal, out var exception) &&
             selfHostedOrganization.CanUseLicense(license, out exception);
 
@@ -54,12 +107,6 @@ public async Task UpdateLicenseAsync(SelfHostedOrganizationDetails selfHostedOrg
             throw new BadRequestException(exception);
         }
 
-        var useAutomaticUserConfirmation = claimsPrincipal?
-            .GetValue<bool>(OrganizationLicenseConstants.UseAutomaticUserConfirmation) ?? false;
-
-        selfHostedOrganization.UseAutomaticUserConfirmation = useAutomaticUserConfirmation;
-        license.UseAutomaticUserConfirmation = useAutomaticUserConfirmation;
-
         await WriteLicenseFileAsync(selfHostedOrganization, license);
         await UpdateOrganizationAsync(selfHostedOrganization, license);
     }

src/Core/Services/Implementations/UserService.cs

@@ -14,6 +14,8 @@
 using Bit.Core.Auth.Enums;
 using Bit.Core.Auth.Models;
 using Bit.Core.Auth.UserFeatures.TwoFactorAuth.Interfaces;
+using Bit.Core.Billing.Licenses;
+using Bit.Core.Billing.Licenses.Extensions;
 using Bit.Core.Billing.Models;
 using Bit.Core.Billing.Models.Business;
 using Bit.Core.Billing.Models.Sales;
@@ -870,7 +872,7 @@
     {
         if (!CoreHelpers.FixedTimeEquals(
                 user.TwoFactorRecoveryCode,
                 recoveryCode.Replace(" ", string.Empty).Trim().ToLower()))
         {
             return false;
         }
@@ -982,6 +984,16 @@
             throw new BadRequestException(exceptionMessage);
         }
 
+        // If the license has a Token (claims-based), extract all properties from claims
+        // Otherwise, fall back to using the properties already on the license object (backward compatibility)
+        if (claimsPrincipal != null)
+        {
+            license.LicenseKey = claimsPrincipal.GetValue<string>(UserLicenseConstants.LicenseKey);
+            license.Premium = claimsPrincipal.GetValue<bool>(UserLicenseConstants.Premium);
+            license.MaxStorageGb = claimsPrincipal.GetValue<short?>(UserLicenseConstants.MaxStorageGb);
+            license.Expires = claimsPrincipal.GetValue<DateTime?>(UserLicenseConstants.Expires);
+        }
+
         var dir = $"{_globalSettings.LicenseDirectory}/user";
         Directory.CreateDirectory(dir);
         using var fs = File.OpenWrite(Path.Combine(dir, $"{user.Id}.json"));

test/Core.Test/AdminConsole/Entities/OrganizationTests.cs

@@ -1,7 +1,10 @@
-using System.Text.Json;
+using System.Reflection;
+using System.Text.Json;
+using System.Text.RegularExpressions;
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.Auth.Enums;
 using Bit.Core.Auth.Models;
+using Bit.Core.Billing.Organizations.Models;
 using Bit.Test.Common.Helpers;
 using Xunit;
 
@@ -115,4 +118,105 @@ public void UseDisableSmAdsForUsers_CanBeSetToTrue()
 
         Assert.True(organization.UseDisableSmAdsForUsers);
     }
+
+    [Fact]
+    public void UpdateFromLicense_AppliesAllLicenseProperties()
+    {
+        // This test ensures that when a new property is added to OrganizationLicense,
+        // it is also applied to the Organization in UpdateFromLicense().
+        // This is the fourth step in the license synchronization pipeline:
+        // Property → Constant → Claim → Extraction → Application
+
+        // 1. Get all public properties from OrganizationLicense
+        var licenseProperties = typeof(OrganizationLicense)
+            .GetProperties(BindingFlags.Public | BindingFlags.Instance)
+            .Select(p => p.Name)
+            .ToHashSet();
+
+        // 2. Define properties that don't need to be applied to Organization
+        var excludedProperties = new HashSet<string>
+        {
+            // Internal/computed properties
+            "SignatureBytes",             // Computed from Signature property
+            "ValidLicenseVersion",        // Internal property, not serialized
+            "CurrentLicenseFileVersion",  // Constant field, not an instance property
+            "Hash",                       // Signature-related, not applied to org
+            "Signature",                  // Signature-related, not applied to org
+            "Token",                      // The JWT itself, not applied to org
+            "Version",                    // License version, not stored on org
+
+            // Properties intentionally excluded from UpdateFromLicense
+            "Id",                         // Self-hosted org has its own unique Guid
+            "MaxStorageGb",               // Not enforced for self-hosted (per comment in UpdateFromLicense)
+
+            // Properties not stored on Organization model
+            "LicenseType",                // Not a property on Organization
+            "InstallationId",             // Not a property on Organization
+            "Issued",                     // Not a property on Organization
+            "Refresh",                    // Not a property on Organization
+            "ExpirationWithoutGracePeriod", // Not a property on Organization
+            "Trial",                      // Not a property on Organization
+            "Expires",                    // Mapped to ExpirationDate on Organization (different name)
+
+            // Deprecated properties not applied
+            "LimitCollectionCreationDeletion",      // Deprecated, not applied
+            "AllowAdminAccessToAllCollectionItems", // Deprecated, not applied
+        };
+
+        // 3. Get properties that should be applied
+        var propertiesThatShouldBeApplied = licenseProperties
+            .Except(excludedProperties)
+            .ToHashSet();
+
+        // 4. Read Organization.UpdateFromLicense source code
+        var organizationSourcePath = Path.Combine(
+            Directory.GetCurrentDirectory(),
+            "..", "..", "..", "..", "..", "src", "Core", "AdminConsole", "Entities", "Organization.cs");
+        var sourceCode = File.ReadAllText(organizationSourcePath);
+
+        // 5. Find all property assignments in UpdateFromLicense method
+        // Pattern matches: PropertyName = license.PropertyName
+        // This regex looks for assignments like "Name = license.Name" or "ExpirationDate = license.Expires"
+        var assignmentPattern = @"(\w+)\s*=\s*license\.(\w+)";
+        var matches = Regex.Matches(sourceCode, assignmentPattern);
+
+        var appliedProperties = new HashSet<string>();
+        foreach (Match match in matches)
+        {
+            // Get the license property name (right side of assignment)
+            var licensePropertyName = match.Groups[2].Value;
+            appliedProperties.Add(licensePropertyName);
+        }
+
+        // Special case: Expires is mapped to ExpirationDate
+        if (appliedProperties.Contains("Expires"))
+        {
+            appliedProperties.Add("Expires"); // Already added, but being explicit
+        }
+
+        // 6. Find missing applications
+        var missingApplications = propertiesThatShouldBeApplied
+            .Except(appliedProperties)
+            .OrderBy(p => p)
+            .ToList();
+
+        // 7. Build error message with guidance
+        var errorMessage = "";
+        if (missingApplications.Any())
+        {
+            errorMessage = $"The following OrganizationLicense properties are NOT applied to Organization in UpdateFromLicense():\n";
+            errorMessage += string.Join("\n", missingApplications.Select(p => $"  - {p}"));
+            errorMessage += "\n\nPlease add the following lines to Organization.UpdateFromLicense():\n";
+            foreach (var prop in missingApplications)
+            {
+                errorMessage += $"  {prop} = license.{prop};\n";
+            }
+            errorMessage += "\nNote: If the property maps to a different name on Organization (like Expires → ExpirationDate), adjust accordingly.";
+        }
+
+        // 8. Assert - if this fails, the error message guides the developer to add the application
+        Assert.True(
+            !missingApplications.Any(),
+            $"\n{errorMessage}");
+    }
 }

test/Core.Test/Billing/Licenses/LicenseConstantsTests.cs

@@ -0,0 +1,68 @@
+using System.Reflection;
+using Bit.Core.Billing.Licenses;
+using Bit.Core.Billing.Organizations.Models;
+using Xunit;
+
+namespace Bit.Core.Test.Billing.Licenses;
+
+public class LicenseConstantsTests
+{
+    [Fact]
+    public void OrganizationLicenseConstants_HasConstantForEveryLicenseProperty()
+    {
+        // This test ensures that when a new property is added to OrganizationLicense,
+        // a corresponding constant is added to OrganizationLicenseConstants.
+        // This is the first step in the license synchronization pipeline:
+        // Property → Constant → Claim → Extraction → Application
+
+        // 1. Get all public properties from OrganizationLicense
+        var licenseProperties = typeof(OrganizationLicense)
+            .GetProperties(BindingFlags.Public | BindingFlags.Instance)
+            .Select(p => p.Name)
+            .ToHashSet();
+
+        // 2. Get all constants from OrganizationLicenseConstants
+        var constants = typeof(OrganizationLicenseConstants)
+            .GetFields(BindingFlags.Public | BindingFlags.Static)
+            .Where(f => f.IsLiteral && !f.IsInitOnly)
+            .Select(f => f.GetValue(null) as string)
+            .ToHashSet();
+
+        // 3. Define properties that don't need constants (internal/computed/non-claims properties)
+        var excludedProperties = new HashSet<string>
+        {
+            "SignatureBytes",             // Computed from Signature property
+            "ValidLicenseVersion",        // Internal property, not serialized
+            "CurrentLicenseFileVersion",  // Constant field, not an instance property
+            "Hash",                       // Signature-related, not in claims system
+            "Signature",                  // Signature-related, not in claims system
+            "Token",                      // The JWT itself, not a claim within the token
+            "Version"                     // Not in claims system (only in deprecated property-based licenses)
+        };
+
+        // 4. Find license properties without corresponding constants
+        var propertiesWithoutConstants = licenseProperties
+            .Except(constants)
+            .Except(excludedProperties)
+            .OrderBy(p => p)
+            .ToList();
+
+        // 5. Build error message with guidance
+        var errorMessage = "";
+        if (propertiesWithoutConstants.Any())
+        {
+            errorMessage = $"The following OrganizationLicense properties don't have constants in OrganizationLicenseConstants:\n";
+            errorMessage += string.Join("\n", propertiesWithoutConstants.Select(p => $"  - {p}"));
+            errorMessage += "\n\nPlease add the following constants to OrganizationLicenseConstants:\n";
+            foreach (var prop in propertiesWithoutConstants)
+            {
+                errorMessage += $"  public const string {prop} = nameof({prop});\n";
+            }
+        }
+
+        // 6. Assert - if this fails, the error message guides the developer to add the constant
+        Assert.True(
+            !propertiesWithoutConstants.Any(),
+            $"\n{errorMessage}");
+    }
+}