diff --git a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
index 247e364ba4..819076bbb8 100644
--- a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
+++ b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
@@ -109,7 +109,6 @@ namespace Umbraco.Extensions
             var appCaches = AppCaches.Create(requestCache);
 
             services.ConfigureOptions<ConfigureKestrelServerOptions>();
-            services.ConfigureOptions<ConfigureIISServerOptions>();
             services.ConfigureOptions<ConfigureFormOptions>();
 
             IProfiler profiler = GetWebProfiler(config);
diff --git a/src/Umbraco.Web.Common/Security/ConfigureIISServerOptions.cs b/src/Umbraco.Web.Common/Security/ConfigureIISServerOptions.cs
index 4141669c1c..1c1460432f 100644
--- a/src/Umbraco.Web.Common/Security/ConfigureIISServerOptions.cs
+++ b/src/Umbraco.Web.Common/Security/ConfigureIISServerOptions.cs
@@ -1,18 +1,24 @@
+using System;
 using Microsoft.AspNetCore.Builder;
 using Microsoft.Extensions.Options;
 using Umbraco.Cms.Core.Configuration.Models;
 
 namespace Umbraco.Cms.Web.Common.Security
 {
+    [Obsolete("This class is obsolete, as this does not configure your Maximum request length, see https://our.umbraco.com/documentation/Reference/V9-Config/MaximumUploadSizeSettings/ for information about configuring maximum request length")]
     public class ConfigureIISServerOptions : IConfigureOptions<IISServerOptions>
     {
         private readonly IOptions<RuntimeSettings> _runtimeSettings;
 
-        public ConfigureIISServerOptions(IOptions<RuntimeSettings> runtimeSettings) => _runtimeSettings = runtimeSettings;
+        public ConfigureIISServerOptions(IOptions<RuntimeSettings> runtimeSettings) =>
+            _runtimeSettings = runtimeSettings;
+
         public void Configure(IISServerOptions options)
         {
             // convert from KB to bytes
-            options.MaxRequestBodySize = _runtimeSettings.Value.MaxRequestLength.HasValue ? _runtimeSettings.Value.MaxRequestLength.Value * 1024 : uint.MaxValue; // ~4GB is the max supported value for IIS and IIS express.
+            options.MaxRequestBodySize = _runtimeSettings.Value.MaxRequestLength.HasValue
+                ? _runtimeSettings.Value.MaxRequestLength.Value * 1024
+                : uint.MaxValue; // ~4GB is the max supported value for IIS and IIS express.
         }
     }
 }
diff --git a/src/Umbraco.Web.Common/Security/ConfigureKestrelServerOptions.cs b/src/Umbraco.Web.Common/Security/ConfigureKestrelServerOptions.cs
index c11e0d8814..59ec330700 100644
--- a/src/Umbraco.Web.Common/Security/ConfigureKestrelServerOptions.cs
+++ b/src/Umbraco.Web.Common/Security/ConfigureKestrelServerOptions.cs
@@ -11,8 +11,8 @@ namespace Umbraco.Cms.Web.Common.Security
         public ConfigureKestrelServerOptions(IOptions<RuntimeSettings> runtimeSettings) => _runtimeSettings = runtimeSettings;
         public void Configure(KestrelServerOptions options)
         {
-            // convert from KB to bytes
-            options.Limits.MaxRequestBodySize = _runtimeSettings.Value.MaxRequestLength.HasValue ? _runtimeSettings.Value.MaxRequestLength.Value * 1024 : long.MaxValue;
+            // convert from KB to bytes, 52428800 bytes (50 MB) is the same as in the IIS settings
+            options.Limits.MaxRequestBodySize = _runtimeSettings.Value.MaxRequestLength.HasValue ? _runtimeSettings.Value.MaxRequestLength.Value * 1024 : 52428800;
         }
     }
 }
diff --git a/src/Umbraco.Web.UI.Client/src/web.config b/src/Umbraco.Web.UI.Client/src/web.config
index 6903c39608..6d14a9bab7 100644
--- a/src/Umbraco.Web.UI.Client/src/web.config
+++ b/src/Umbraco.Web.UI.Client/src/web.config
@@ -5,4 +5,4 @@
       <clientCache cacheControlCustom="private" cacheControlMode="UseMaxAge" cacheControlMaxAge="3.00:00:00" />
     </staticContent>
   </system.webServer>
-</configuration>
\ No newline at end of file
+</configuration>