diff --git a/src/Umbraco.Web/Mvc/RenderRouteHandler.cs b/src/Umbraco.Web/Mvc/RenderRouteHandler.cs
index 3f3e368cbe..39bf65160a 100644
--- a/src/Umbraco.Web/Mvc/RenderRouteHandler.cs
+++ b/src/Umbraco.Web/Mvc/RenderRouteHandler.cs
@@ -334,8 +334,11 @@ namespace Umbraco.Web.Mvc
 					requestContext.HttpContext.Response.Redirect(publishedContentRequest.RedirectUrl, true);
 					return null;
 				}
-				if (publishedContentRequest.Is404) // should always be the case
-					requestContext.HttpContext.Response.StatusCode = 404;
+                if (publishedContentRequest.Is404) // should always be the case
+                {
+                    requestContext.HttpContext.Response.StatusCode = 404;
+                    requestContext.HttpContext.Response.TrySkipIisCustomErrors = true;
+                }
 				var handler = GetHandlerOnMissingTemplate(publishedContentRequest);
 
 				// if it's not null it can be either the PublishedContentNotFoundHandler (no document was
diff --git a/src/Umbraco.Web/UmbracoModule.cs b/src/Umbraco.Web/UmbracoModule.cs
index 6509c478dd..a6abe152b9 100644
--- a/src/Umbraco.Web/UmbracoModule.cs
+++ b/src/Umbraco.Web/UmbracoModule.cs
@@ -115,8 +115,11 @@ namespace Umbraco.Web
 				httpContext.Response.Redirect(pcr.RedirectUrl, true);
 				return;
 			}
-			if (pcr.Is404)
-				httpContext.Response.StatusCode = 404;
+            if (pcr.Is404)
+            {
+                httpContext.Response.StatusCode = 404;
+                httpContext.Response.TrySkipIisCustomErrors = true;
+            }
 			if (!pcr.HasPublishedContent)
 				httpContext.RemapHandler(new PublishedContentNotFoundHandler());
 			else