diff --git a/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs b/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs
index 11eaa3bb8a31..c2fa07f21b7f 100644
--- a/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs
+++ b/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs
@@ -6,7 +6,6 @@
 using Umbraco.Cms.Core.Configuration.Models;
 using Umbraco.Cms.Core.Models;
 using Umbraco.Cms.Core.Scoping;
-using Umbraco.Cms.Core.Serialization;
 using Umbraco.Cms.Core.Services;
 
 namespace Umbraco.Cms.Infrastructure.BackgroundJobs.Jobs;
@@ -15,11 +14,11 @@ public class WebhookFiring : IRecurringBackgroundJob
 {
     private readonly ILogger<WebhookFiring> _logger;
     private readonly IWebhookRequestService _webhookRequestService;
-    private readonly IJsonSerializer _jsonSerializer;
     private readonly IWebhookLogFactory _webhookLogFactory;
     private readonly IWebhookLogService _webhookLogService;
     private readonly IWebhookService _webHookService;
     private readonly ICoreScopeProvider _coreScopeProvider;
+    private readonly IHttpClientFactory _httpClientFactory;
     private WebhookSettings _webhookSettings;
 
     public TimeSpan Period => _webhookSettings.Period;
@@ -32,20 +31,20 @@ public event EventHandler PeriodChanged { add { } remove { } }
     public WebhookFiring(
         ILogger<WebhookFiring> logger,
         IWebhookRequestService webhookRequestService,
-        IJsonSerializer jsonSerializer,
         IWebhookLogFactory webhookLogFactory,
         IWebhookLogService webhookLogService,
         IWebhookService webHookService,
         IOptionsMonitor<WebhookSettings> webhookSettings,
-        ICoreScopeProvider coreScopeProvider)
+        ICoreScopeProvider coreScopeProvider,
+        IHttpClientFactory httpClientFactory)
     {
         _logger = logger;
         _webhookRequestService = webhookRequestService;
-        _jsonSerializer = jsonSerializer;
         _webhookLogFactory = webhookLogFactory;
         _webhookLogService = webhookLogService;
         _webHookService = webHookService;
         _coreScopeProvider = coreScopeProvider;
+        _httpClientFactory = httpClientFactory;
         _webhookSettings = webhookSettings.CurrentValue;
         webhookSettings.OnChange(x => _webhookSettings = x);
     }
@@ -90,10 +89,11 @@ await Task.WhenAll(requests.Select(request =>
 
     private async Task<HttpResponseMessage?> SendRequestAsync(IWebhook webhook, string eventName, string? serializedObject, int retryCount, CancellationToken cancellationToken)
     {
-        using var httpClient = new HttpClient();
+        using HttpClient httpClient = _httpClientFactory.CreateClient();
 
         var stringContent = new StringContent(serializedObject ?? string.Empty, Encoding.UTF8, MediaTypeNames.Application.Json);
         stringContent.Headers.TryAddWithoutValidation("Umb-Webhook-Event", eventName);
+        stringContent.Headers.TryAddWithoutValidation("Umb-Webhook-RetryCount", retryCount.ToString());
 
         foreach (KeyValuePair<string, string> header in webhook.Headers)
         {
@@ -107,7 +107,7 @@ await Task.WhenAll(requests.Select(request =>
         }
         catch (Exception ex)
         {
-            _logger.LogError(ex, "Error while sending webhook request for webhook {WebhookKey}.", webhook);
+            _logger.LogError(ex, "Error while sending webhook request for webhook {WebhookKey}.", webhook.Key);
         }
 
         var webhookResponseModel = new WebhookResponseModel