diff --git a/src/Api/Controllers/OrganizationConnectionsController.cs b/src/Api/Controllers/OrganizationConnectionsController.cs
index 73754dba76..13260b7cca 100644
--- a/src/Api/Controllers/OrganizationConnectionsController.cs
+++ b/src/Api/Controllers/OrganizationConnectionsController.cs
@@ -96,7 +96,7 @@ public class OrganizationConnectionsController : Controller
         switch (model.Type)
         {
             case OrganizationConnectionType.CloudBillingSync:
-                return await CreateOrUpdateOrganizationConnectionAsync<BillingSyncConfig>(organizationConnectionId, model);
+                return await CreateOrUpdateOrganizationConnectionAsync<BillingSyncConfig>(organizationConnectionId, model, ValidateBillingSyncConfig);
             case OrganizationConnectionType.Scim:
                 return await CreateOrUpdateOrganizationConnectionAsync<ScimConfig>(organizationConnectionId, model);
             default:
diff --git a/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs b/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
index 80bfcfe006..594e708bdf 100644
--- a/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
+++ b/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
@@ -214,6 +214,7 @@ public class OrganizationConnectionsControllerTests
         updated.Type = OrganizationConnectionType.CloudBillingSync;
         var model = RequestModelFromEntity<BillingSyncConfig>(updated);
 
+        sutProvider.GetDependency<IGlobalSettings>().SelfHosted.Returns(true);
         sutProvider.GetDependency<ICurrentContext>().OrganizationOwner(model.OrganizationId).Returns(true);
         sutProvider.GetDependency<IOrganizationConnectionRepository>()
             .GetByOrganizationIdTypeAsync(model.OrganizationId, model.Type)
@@ -225,6 +226,23 @@ public class OrganizationConnectionsControllerTests
             .GetByIdAsync(existing.Id)
             .Returns(existing);
 
+        OrganizationLicense organizationLicense = new OrganizationLicense();
+        var now = DateTime.UtcNow;
+        organizationLicense.Issued = now.AddDays(-10);
+        organizationLicense.Expires = now.AddDays(10);
+        organizationLicense.Version = 1;
+        organizationLicense.UsersGetPremium = true;
+        organizationLicense.Id = config.CloudOrganizationId;
+        organizationLicense.Trial = true;
+
+        sutProvider.GetDependency<ILicensingService>()
+            .ReadOrganizationLicenseAsync(Arg.Any<Guid>())
+            .Returns(organizationLicense);
+
+        sutProvider.GetDependency<ILicensingService>()
+            .VerifyLicense(organizationLicense)
+            .Returns(true);
+
         var expected = new OrganizationConnectionResponseModel(updated, typeof(BillingSyncConfig));
         var result = await sutProvider.Sut.UpdateConnection(existing.Id, model);
 
@@ -233,6 +251,51 @@ public class OrganizationConnectionsControllerTests
             .UpdateAsync(Arg.Is(AssertHelper.AssertPropertyEqual(model.ToData(updated.Id))));
     }
 
+    [Theory]
+    [BitAutoData]
+    public async Task UpdateConnection_BillingSyncType_InvalidLicense_ErrorThrows(OrganizationConnection existing, BillingSyncConfig config,
+        OrganizationConnection updated,
+        SutProvider<OrganizationConnectionsController> sutProvider)
+    {
+        existing.SetConfig(new BillingSyncConfig
+        {
+            CloudOrganizationId = config.CloudOrganizationId,
+        });
+        updated.Config = JsonSerializer.Serialize(config);
+        updated.Id = existing.Id;
+        updated.Type = OrganizationConnectionType.CloudBillingSync;
+        var model = RequestModelFromEntity<BillingSyncConfig>(updated);
+        sutProvider.GetDependency<IGlobalSettings>().SelfHosted.Returns(true);
+        sutProvider.GetDependency<ICurrentContext>().OrganizationOwner(model.OrganizationId).Returns(true);
+        sutProvider.GetDependency<IOrganizationConnectionRepository>()
+            .GetByOrganizationIdTypeAsync(model.OrganizationId, model.Type)
+            .Returns(new[] { existing });
+        sutProvider.GetDependency<IUpdateOrganizationConnectionCommand>()
+            .UpdateAsync<BillingSyncConfig>(default)
+            .ReturnsForAnyArgs(updated);
+        sutProvider.GetDependency<IOrganizationConnectionRepository>()
+            .GetByIdAsync(existing.Id)
+            .Returns(existing);
+
+        OrganizationLicense organizationLicense = new OrganizationLicense();
+        var now = DateTime.UtcNow;
+        organizationLicense.Issued = now.AddDays(-10);
+        organizationLicense.Expires = now.AddDays(10);
+        organizationLicense.Version = 1;
+        organizationLicense.UsersGetPremium = true;
+        organizationLicense.Id = config.CloudOrganizationId;
+        organizationLicense.Trial = true;
+
+        sutProvider.GetDependency<ILicensingService>()
+                    .VerifyLicense(organizationLicense)
+                    .Returns(false);
+
+        var exception = await Assert.ThrowsAsync<BadRequestException>(async () => await sutProvider.Sut.UpdateConnection(existing.Id, model));
+
+        Assert.Contains("Cannot verify license file.", exception.Message);
+
+    }
+
     [Theory]
     [BitAutoData]
     public async Task UpdateConnection_DoesNotExist_ThrowsNotFound(SutProvider<OrganizationConnectionsController> sutProvider)