diff --git a/src/Admin/Controllers/OrganizationsController.cs b/src/Admin/Controllers/OrganizationsController.cs
index a568f03d2..6752fed89 100644
--- a/src/Admin/Controllers/OrganizationsController.cs
+++ b/src/Admin/Controllers/OrganizationsController.cs
@@ -14,6 +14,7 @@ using Bit.Core.Settings;
 using Bit.Core.Utilities;
 using Microsoft.AspNetCore.Authorization;
 using Microsoft.AspNetCore.Mvc;
+using Microsoft.Extensions.Logging;
 
 namespace Bit.Admin.Controllers
 {
@@ -34,6 +35,7 @@ namespace Bit.Admin.Controllers
         private readonly GlobalSettings _globalSettings;
         private readonly IReferenceEventService _referenceEventService;
         private readonly IUserService _userService;
+        private readonly ILogger<OrganizationsController> _logger;
 
         public OrganizationsController(
             IOrganizationRepository organizationRepository,
@@ -49,7 +51,8 @@ namespace Bit.Admin.Controllers
             IApplicationCacheService applicationCacheService,
             GlobalSettings globalSettings,
             IReferenceEventService referenceEventService,
-            IUserService userService)
+            IUserService userService,
+            ILogger<OrganizationsController> logger)
         {
             _organizationRepository = organizationRepository;
             _organizationUserRepository = organizationUserRepository;
@@ -65,6 +68,7 @@ namespace Bit.Admin.Controllers
             _globalSettings = globalSettings;
             _referenceEventService = referenceEventService;
             _userService = userService;
+            _logger = logger;
         }
 
         public async Task<IActionResult> Index(string name = null, string userEmail = null, bool? paid = null,
@@ -199,6 +203,7 @@ namespace Bit.Admin.Controllers
                 catch (Exception ex)
                 {
                     TempData["ConnectionError"] = ex.Message;
+                    _logger.LogWarning(ex, "Error while attempting to do billing sync for organization with id '{OrganizationId}'", id);
                 }
 
                 if (_globalSettings.SelfHosted)
diff --git a/src/Api/Controllers/OrganizationConnectionsController.cs b/src/Api/Controllers/OrganizationConnectionsController.cs
index ff695252c..9f9090d57 100644
--- a/src/Api/Controllers/OrganizationConnectionsController.cs
+++ b/src/Api/Controllers/OrganizationConnectionsController.cs
@@ -74,6 +74,10 @@ namespace Bit.Api.Controllers
                 case OrganizationConnectionType.CloudBillingSync:
                     var typedModel = new OrganizationConnectionRequestModel<BillingSyncConfig>(model);
                     var license = await _licensingService.ReadOrganizationLicenseAsync(model.OrganizationId);
+                    if (!_licensingService.VerifyLicense(license))
+                    {
+                        throw new BadRequestException("Cannot verify license file.");
+                    }
                     typedModel.ParsedConfig.CloudOrganizationId = license.Id;
                     var connection = await _createOrganizationConnectionCommand.CreateAsync(typedModel.ToData());
                     return new OrganizationConnectionResponseModel(connection, typeof(BillingSyncConfig));
diff --git a/src/Core/OrganizationFeatures/OrganizationSponsorships/FamiliesForEnterprise/SelfHosted/SelfHostedSyncSponsorshipsCommand.cs b/src/Core/OrganizationFeatures/OrganizationSponsorships/FamiliesForEnterprise/SelfHosted/SelfHostedSyncSponsorshipsCommand.cs
index f89c490ca..848d52012 100644
--- a/src/Core/OrganizationFeatures/OrganizationSponsorships/FamiliesForEnterprise/SelfHosted/SelfHostedSyncSponsorshipsCommand.cs
+++ b/src/Core/OrganizationFeatures/OrganizationSponsorships/FamiliesForEnterprise/SelfHosted/SelfHostedSyncSponsorshipsCommand.cs
@@ -87,6 +87,7 @@ namespace Bit.Core.OrganizationFeatures.OrganizationSponsorships.FamiliesForEnte
 
                 if (response == null)
                 {
+                    _logger.LogDebug("Organization sync failed for '{OrgId}'", organizationId);
                     throw new BadRequestException("Organization sync failed");
                 }
 
diff --git a/src/Core/Services/Implementations/BaseIdentityClientService.cs b/src/Core/Services/Implementations/BaseIdentityClientService.cs
index 61ed13d01..a341b2820 100644
--- a/src/Core/Services/Implementations/BaseIdentityClientService.cs
+++ b/src/Core/Services/Implementations/BaseIdentityClientService.cs
@@ -124,11 +124,19 @@ namespace Bit.Core.Services
 
             if (!response.IsSuccessStatusCode)
             {
+                _logger.LogInformation("Unsuccessful token response with status code {StatusCode}", response.StatusCode);
+
                 if (response.StatusCode == HttpStatusCode.BadRequest)
                 {
                     _nextAuthAttempt = DateTime.UtcNow.AddDays(1);
                 }
 
+                if (_logger.IsEnabled(LogLevel.Debug))
+                {
+                    var responseBody = await response.Content.ReadAsStringAsync();
+                    _logger.LogDebug("Error response body:\n{ResponseBody}", responseBody);
+                }
+
                 return false;
             }
 
diff --git a/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs b/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
index 7d1268460..f7fa3fca3 100644
--- a/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
+++ b/test/Api.Test/Controllers/OrganizationConnectionsControllerTests.cs
@@ -83,9 +83,39 @@ namespace Bit.Api.Test.Controllers
 
         [Theory]
         [BitAutoData]
-        public async Task CreateConnection_Success(OrganizationConnectionRequestModel model, BillingSyncConfig config,
-            Guid cloudOrgId, SutProvider<OrganizationConnectionsController> sutProvider)
+        public async Task CreateConnection_BillingSyncType_InvalidLicense_Throws(OrganizationConnectionRequestModel model,
+            BillingSyncConfig config, Guid cloudOrgId, OrganizationLicense organizationLicense,
+            SutProvider<OrganizationConnectionsController> sutProvider)
         {
+            model.Type = OrganizationConnectionType.CloudBillingSync;
+            organizationLicense.Id = cloudOrgId;
+
+            model.Config = JsonDocumentFromObject(config);
+            var typedModel = new OrganizationConnectionRequestModel<BillingSyncConfig>(model);
+            typedModel.ParsedConfig.CloudOrganizationId = cloudOrgId;
+
+            sutProvider.GetDependency<ICurrentContext>()
+                .OrganizationOwner(model.OrganizationId)
+                .Returns(true);
+
+            sutProvider.GetDependency<ILicensingService>()
+                .ReadOrganizationLicenseAsync(model.OrganizationId)
+                .Returns(organizationLicense);
+
+            sutProvider.GetDependency<ILicensingService>()
+                .VerifyLicense(organizationLicense)
+                .Returns(false);
+
+            await Assert.ThrowsAsync<BadRequestException>(async () => await sutProvider.Sut.CreateConnection(model));
+        }
+
+        [Theory]
+        [BitAutoData]
+        public async Task CreateConnection_Success(OrganizationConnectionRequestModel model, BillingSyncConfig config,
+            Guid cloudOrgId, OrganizationLicense organizationLicense, SutProvider<OrganizationConnectionsController> sutProvider)
+        {
+            organizationLicense.Id = cloudOrgId;
+
             model.Config = JsonDocumentFromObject(config);
             var typedModel = new OrganizationConnectionRequestModel<BillingSyncConfig>(model);
             typedModel.ParsedConfig.CloudOrganizationId = cloudOrgId;
@@ -95,10 +125,11 @@ namespace Bit.Api.Test.Controllers
             sutProvider.GetDependency<ICurrentContext>().OrganizationOwner(model.OrganizationId).Returns(true);
             sutProvider.GetDependency<ILicensingService>()
                 .ReadOrganizationLicenseAsync(Arg.Any<Guid>())
-                .Returns(new OrganizationLicense
-                {
-                    Id = cloudOrgId,
-                });
+                .Returns(organizationLicense);
+
+            sutProvider.GetDependency<ILicensingService>()
+                .VerifyLicense(organizationLicense)
+                .Returns(true);
 
             await sutProvider.Sut.CreateConnection(model);