diff --git a/src/Umbraco.Core/Constants-Telemetry.cs b/src/Umbraco.Core/Constants-Telemetry.cs
index f8a382b0bb..0e7c96d250 100644
--- a/src/Umbraco.Core/Constants-Telemetry.cs
+++ b/src/Umbraco.Core/Constants-Telemetry.cs
@@ -29,5 +29,6 @@ public static partial class Constants
         public static string DatabaseProvider = "DatabaseProvider";
         public static string CurrentServerRole = "CurrentServerRole";
         public static string RuntimeMode = "RuntimeMode";
+        public static string BackofficeExternalLoginProviderCount = "BackofficeExternalLoginProviderCount";
     }
 }
diff --git a/src/Umbraco.Core/EmbeddedResources/Lang/en_us.xml b/src/Umbraco.Core/EmbeddedResources/Lang/en_us.xml
index d85e6d7eb4..035d0e42f1 100644
--- a/src/Umbraco.Core/EmbeddedResources/Lang/en_us.xml
+++ b/src/Umbraco.Core/EmbeddedResources/Lang/en_us.xml
@@ -3010,7 +3010,7 @@ To manage your website, simply open the Umbraco backoffice and start adding cont
           We will send:
           <ul>
             <li>Anonymized site ID, Umbraco version, and packages installed.</li>
-            <li>Number of: Root nodes, Content nodes, Macros, Media, Document Types, Templates, Languages, Domains, User Group, Users, Members, and Property Editors in use.</li>
+            <li>Number of: Root nodes, Content nodes, Macros, Media, Document Types, Templates, Languages, Domains, User Group, Users, Members, Backoffice external login providers, and Property Editors in use.</li>
             <li>System information: Webserver, server OS, server framework, server OS language, and database provider.</li>
             <li>Configuration settings: Modelsbuilder mode, if custom Umbraco path exists, ASP environment, and if you are in debug mode.</li>
           </ul>
diff --git a/src/Umbraco.Infrastructure/Telemetry/Interfaces/IDetailedTelemetryProvider.cs b/src/Umbraco.Infrastructure/Telemetry/Interfaces/IDetailedTelemetryProvider.cs
index b21b216e68..e6ce3b005f 100644
--- a/src/Umbraco.Infrastructure/Telemetry/Interfaces/IDetailedTelemetryProvider.cs
+++ b/src/Umbraco.Infrastructure/Telemetry/Interfaces/IDetailedTelemetryProvider.cs
@@ -2,7 +2,7 @@ using Umbraco.Cms.Core.Models;
 
 namespace Umbraco.Cms.Infrastructure.Telemetry.Interfaces;
 
-internal interface IDetailedTelemetryProvider
+public interface IDetailedTelemetryProvider
 {
     IEnumerable<UsageInformation> GetInformation();
 }
diff --git a/src/Umbraco.Web.BackOffice/Controllers/TinyMceController.cs b/src/Umbraco.Web.BackOffice/Controllers/TinyMceController.cs
index 3d93f9af6c..a9f81344a0 100644
--- a/src/Umbraco.Web.BackOffice/Controllers/TinyMceController.cs
+++ b/src/Umbraco.Web.BackOffice/Controllers/TinyMceController.cs
@@ -26,6 +26,19 @@ public class TinyMceController : UmbracoAuthorizedApiController
     private readonly IIOHelper _ioHelper;
     private readonly IShortStringHelper _shortStringHelper;
 
+    private readonly Dictionary<string, string> _fileContentTypeMappings =
+        new()
+        {
+            { "image/png", "png" },
+            { "image/jpeg", "jpg" },
+            { "image/gif", "gif" },
+            { "image/bmp", "bmp" },
+            { "image/x-icon", "ico" },
+            { "image/svg+xml", "svg" },
+            { "image/tiff", "tiff" },
+            { "image/webp", "webp" },
+        };
+
     public TinyMceController(
         IHostingEnvironment hostingEnvironment,
         IShortStringHelper shortStringHelper,
@@ -43,16 +56,6 @@ public class TinyMceController : UmbracoAuthorizedApiController
     [HttpPost]
     public async Task<IActionResult> UploadImage(List<IFormFile> file)
     {
-        // Create an unique folder path to help with concurrent users to avoid filename clash
-        var imageTempPath =
-            _hostingEnvironment.MapPathContentRoot(Constants.SystemDirectories.TempImageUploads + "/" + Guid.NewGuid());
-
-        // Ensure image temp path exists
-        if (Directory.Exists(imageTempPath) == false)
-        {
-            Directory.CreateDirectory(imageTempPath);
-        }
-
         // Must have a file
         if (file.Count == 0)
         {
@@ -65,13 +68,36 @@ public class TinyMceController : UmbracoAuthorizedApiController
             return new UmbracoProblemResult("Only one file can be uploaded at a time", HttpStatusCode.BadRequest);
         }
 
+        // Create an unique folder path to help with concurrent users to avoid filename clash
+        var imageTempPath =
+            _hostingEnvironment.MapPathContentRoot(Constants.SystemDirectories.TempImageUploads + "/" + Guid.NewGuid());
+
+        // Ensure image temp path exists
+        if (Directory.Exists(imageTempPath) == false)
+        {
+            Directory.CreateDirectory(imageTempPath);
+        }
+
         IFormFile formFile = file.First();
 
         // Really we should only have one file per request to this endpoint
         //  var file = result.FileData[0];
-        var fileName = formFile.FileName.Trim(new[] { '\"' }).TrimEnd();
+        var fileName = formFile.FileName.Trim(new[] {'\"'}).TrimEnd();
         var safeFileName = fileName.ToSafeFileName(_shortStringHelper);
-        var ext = safeFileName.Substring(safeFileName.LastIndexOf('.') + 1).ToLowerInvariant();
+        string ext;
+        var fileExtensionIndex = safeFileName.LastIndexOf('.');
+        if (fileExtensionIndex is not -1)
+        {
+            ext = safeFileName.Substring(fileExtensionIndex + 1).ToLowerInvariant();
+        }
+        else
+        {
+            _fileContentTypeMappings.TryGetValue(formFile.ContentType, out var fileExtension);
+            ext = fileExtension ?? string.Empty;
+
+            // safeFileName will not have a file extension, so we need to add it back
+            safeFileName += $".{ext}";
+        }
 
         if (_contentSettings.IsFileAllowedForUpload(ext) == false ||
             _imageUrlGenerator.IsSupportedImageFormat(ext) == false)
diff --git a/src/Umbraco.Web.BackOffice/DependencyInjection/UmbracoBuilder.BackOfficeIdentity.cs b/src/Umbraco.Web.BackOffice/DependencyInjection/UmbracoBuilder.BackOfficeIdentity.cs
index 6d3ff7edda..1844cf5885 100644
--- a/src/Umbraco.Web.BackOffice/DependencyInjection/UmbracoBuilder.BackOfficeIdentity.cs
+++ b/src/Umbraco.Web.BackOffice/DependencyInjection/UmbracoBuilder.BackOfficeIdentity.cs
@@ -11,7 +11,9 @@ using Umbraco.Cms.Core.Scoping;
 using Umbraco.Cms.Core.Security;
 using Umbraco.Cms.Core.Services;
 using Umbraco.Cms.Infrastructure.Security;
+using Umbraco.Cms.Infrastructure.Telemetry.Interfaces;
 using Umbraco.Cms.Web.BackOffice.Security;
+using Umbraco.Cms.Web.BackOffice.Telemetry;
 using Umbraco.Cms.Web.Common.AspNetCore;
 using Umbraco.Cms.Web.Common.Security;
 
@@ -65,6 +67,7 @@ public static partial class UmbracoBuilderExtensions
         services.TryAddScoped<IIpResolver, AspNetCoreIpResolver>();
         services.TryAddSingleton<IBackOfficeExternalLoginProviders, BackOfficeExternalLoginProviders>();
         services.TryAddSingleton<IBackOfficeTwoFactorOptions, DefaultBackOfficeTwoFactorOptions>();
+        services.AddTransient<IDetailedTelemetryProvider, ExternalLoginTelemetryProvider>();
 
         return new BackOfficeIdentityBuilder(services);
     }
diff --git a/src/Umbraco.Web.BackOffice/Telemetry/ExternalLoginTelemetryProvider.cs b/src/Umbraco.Web.BackOffice/Telemetry/ExternalLoginTelemetryProvider.cs
new file mode 100644
index 0000000000..21a59796b3
--- /dev/null
+++ b/src/Umbraco.Web.BackOffice/Telemetry/ExternalLoginTelemetryProvider.cs
@@ -0,0 +1,22 @@
+using Umbraco.Cms.Core;
+using Umbraco.Cms.Core.Models;
+using Umbraco.Cms.Infrastructure.Telemetry.Interfaces;
+using Umbraco.Cms.Web.BackOffice.Security;
+
+namespace Umbraco.Cms.Web.BackOffice.Telemetry;
+
+public class ExternalLoginTelemetryProvider : IDetailedTelemetryProvider
+{
+    private readonly IBackOfficeExternalLoginProviders _externalLoginProviders;
+
+    public ExternalLoginTelemetryProvider(IBackOfficeExternalLoginProviders externalLoginProviders)
+    {
+        _externalLoginProviders = externalLoginProviders;
+    }
+
+    public IEnumerable<UsageInformation> GetInformation()
+    {
+        IEnumerable<BackOfficeExternaLoginProviderScheme> providers = _externalLoginProviders.GetBackOfficeProvidersAsync().GetAwaiter().GetResult();
+        yield return new UsageInformation(Constants.Telemetry.BackofficeExternalLoginProviderCount, providers.Count());
+    }
+}
diff --git a/tests/Umbraco.Tests.Integration/Umbraco.Core/Telemetry/TelemetryServiceTests.cs b/tests/Umbraco.Tests.Integration/Umbraco.Core/Telemetry/TelemetryServiceTests.cs
index bc4b68b508..a310caa164 100644
--- a/tests/Umbraco.Tests.Integration/Umbraco.Core/Telemetry/TelemetryServiceTests.cs
+++ b/tests/Umbraco.Tests.Integration/Umbraco.Core/Telemetry/TelemetryServiceTests.cs
@@ -50,7 +50,8 @@ public class TelemetryServiceTests : UmbracoIntegrationTest
             Constants.Telemetry.IsDebug,
             Constants.Telemetry.DatabaseProvider,
             Constants.Telemetry.CurrentServerRole,
-            Constants.Telemetry.RuntimeMode,
+            Constants.Telemetry.BackofficeExternalLoginProviderCount,
+            Constants.Telemetry.RuntimeMode
         };
 
         MetricsConsentService.SetConsentLevel(TelemetryLevel.Detailed);
diff --git a/tests/Umbraco.Tests.Integration/Umbraco.Examine.Lucene/UmbracoExamine/IndexInitializer.cs b/tests/Umbraco.Tests.Integration/Umbraco.Examine.Lucene/UmbracoExamine/IndexInitializer.cs
index b287f6fbf3..01ca9284f7 100644
--- a/tests/Umbraco.Tests.Integration/Umbraco.Examine.Lucene/UmbracoExamine/IndexInitializer.cs
+++ b/tests/Umbraco.Tests.Integration/Umbraco.Examine.Lucene/UmbracoExamine/IndexInitializer.cs
@@ -19,6 +19,7 @@ using Umbraco.Cms.Core.Services;
 using Umbraco.Cms.Core.Strings;
 using Umbraco.Cms.Infrastructure.Examine;
 using Umbraco.Cms.Infrastructure.Persistence;
+using Umbraco.Cms.Web.Common.DependencyInjection;
 using Directory = Lucene.Net.Store.Directory;
 using StaticServiceProvider = Umbraco.Cms.Core.DependencyInjection.StaticServiceProvider;