diff --git a/src/Umbraco.Core/Constants-HttpClients.cs b/src/Umbraco.Core/Constants-HttpClients.cs
index 677f442085..a9c693f39d 100644
--- a/src/Umbraco.Core/Constants-HttpClients.cs
+++ b/src/Umbraco.Core/Constants-HttpClients.cs
@@ -14,5 +14,18 @@ public static partial class Constants
         ///     Name for http client which ignores certificate errors.
         /// </summary>
         public const string IgnoreCertificateErrors = "Umbraco:HttpClients:IgnoreCertificateErrors";
+
+        /// <summary>
+        ///     Name for http client which sends webhook requests.
+        /// </summary>
+        public const string WebhookFiring = "Umbraco:HttpClients:WebhookFiring";
+
+        public static class Headers
+        {
+            /// <summary>
+            ///     User agent name for the product name.
+            /// </summary>
+            public const string UserAgentProductName = "Umbraco-Cms";
+        }
     }
 }
diff --git a/src/Umbraco.Core/Media/EmbedProviders/OEmbedProviderBase.cs b/src/Umbraco.Core/Media/EmbedProviders/OEmbedProviderBase.cs
index 9385dcf6c9..59d0f171ef 100644
--- a/src/Umbraco.Core/Media/EmbedProviders/OEmbedProviderBase.cs
+++ b/src/Umbraco.Core/Media/EmbedProviders/OEmbedProviderBase.cs
@@ -55,7 +55,7 @@ public abstract class OEmbedProviderBase : IEmbedProvider
         if (_httpClient == null)
         {
             _httpClient = new HttpClient();
-            _httpClient.DefaultRequestHeaders.UserAgent.TryParseAdd("Umbraco-CMS");
+            _httpClient.DefaultRequestHeaders.UserAgent.TryParseAdd(Constants.HttpClients.Headers.UserAgentProductName);
         }
 
         using (var request = new HttpRequestMessage(HttpMethod.Get, url))
diff --git a/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs b/src/Umbraco.Infrastructure/BackgroundJobs/Jobs/WebhookFiring.cs
index 11eaa3bb8a..3d16960144 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;
 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 class WebhookFiring : IRecurringBackgroundJob
     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);
     }
@@ -72,8 +71,7 @@ public class WebhookFiring : IRecurringBackgroundJob
                         return;
                     }
 
-                    HttpResponseMessage? response = await SendRequestAsync(webhook, request.EventAlias, request.RequestObject, request.RetryCount, CancellationToken.None);
-
+                    using HttpResponseMessage? response = await SendRequestAsync(webhook, request.EventAlias, request.RequestObject, request.RetryCount, CancellationToken.None);
                     if ((response?.IsSuccessStatusCode ?? false) || request.RetryCount >= _webhookSettings.MaximumRetries)
                     {
                         await _webhookRequestService.DeleteAsync(request);
@@ -90,24 +88,36 @@ public class WebhookFiring : IRecurringBackgroundJob
 
     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(Constants.HttpClients.WebhookFiring);
 
-        var stringContent = new StringContent(serializedObject ?? string.Empty, Encoding.UTF8, MediaTypeNames.Application.Json);
-        stringContent.Headers.TryAddWithoutValidation("Umb-Webhook-Event", eventName);
-
-        foreach (KeyValuePair<string, string> header in webhook.Headers)
+        using var request = new HttpRequestMessage(HttpMethod.Post, webhook.Url)
         {
-            stringContent.Headers.TryAddWithoutValidation(header.Key, header.Value);
-        }
+            Version = httpClient.DefaultRequestVersion,
+            VersionPolicy = httpClient.DefaultVersionPolicy,
+        };
 
         HttpResponseMessage? response = null;
         try
         {
-            response = await httpClient.PostAsync(webhook.Url, stringContent, cancellationToken);
+            // Add headers
+            request.Headers.Add("Umb-Webhook-Event", eventName);
+            request.Headers.Add("Umb-Webhook-RetryCount", retryCount.ToString());
+            request.Headers.Add("Umb-Webhook-Date", DateTime.Now.ToString("R"));
+
+            foreach (KeyValuePair<string, string> header in webhook.Headers)
+            {
+                request.Headers.Add(header.Key, header.Value);
+            }
+
+            // Set content
+            request.Content = new StringContent(serializedObject ?? string.Empty, Encoding.UTF8, MediaTypeNames.Application.Json);
+
+            // Send request
+            response = await httpClient.SendAsync(request, cancellationToken);
         }
         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
diff --git a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
index 40436fd798..8939b6fcb4 100644
--- a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
+++ b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
@@ -1,4 +1,5 @@
 using System.Data.Common;
+using System.Net.Http.Headers;
 using System.Reflection;
 using Dazinator.Extensions.FileProviders.GlobPatternFilter;
 using Microsoft.AspNetCore.Builder;
@@ -10,7 +11,6 @@ using Microsoft.AspNetCore.Server.Kestrel.Core;
 using Microsoft.Extensions.Configuration;
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.DependencyInjection.Extensions;
-using Microsoft.Extensions.Hosting;
 using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 using Serilog.Extensions.Logging;
@@ -23,6 +23,7 @@ using Umbraco.Cms.Core;
 using Umbraco.Cms.Core.Blocks;
 using Umbraco.Cms.Core.Cache;
 using Umbraco.Cms.Core.Composing;
+using Umbraco.Cms.Core.Configuration;
 using Umbraco.Cms.Core.Configuration.Models;
 using Umbraco.Cms.Core.DependencyInjection;
 using Umbraco.Cms.Core.Diagnostics;
@@ -261,6 +262,11 @@ public static partial class UmbracoBuilderExtensions
                 ServerCertificateCustomValidationCallback =
                     HttpClientHandler.DangerousAcceptAnyServerCertificateValidator,
             });
+        builder.Services.AddHttpClient(Constants.HttpClients.WebhookFiring, (services, client) =>
+        {
+            var productVersion = services.GetRequiredService<IUmbracoVersion>().SemanticVersion.ToSemanticStringWithoutBuild();
+            client.DefaultRequestHeaders.UserAgent.Add(new ProductInfoHeaderValue(Constants.HttpClients.Headers.UserAgentProductName, productVersion));
+        });
         return builder;
     }