diff --git a/src/Umbraco.Core/ObjectResolution/ApplicationEventsResolver.cs b/src/Umbraco.Core/ObjectResolution/ApplicationEventsResolver.cs
index ab5e31b2d3..4b12ada30e 100644
--- a/src/Umbraco.Core/ObjectResolution/ApplicationEventsResolver.cs
+++ b/src/Umbraco.Core/ObjectResolution/ApplicationEventsResolver.cs
@@ -75,5 +75,19 @@ namespace Umbraco.Core.ObjectResolution
             }
 	    }
 
+	    private class LegacyStartupHandlerResolver : ManyObjectsResolverBase<ApplicationEventsResolver, IApplicationStartupHandler>
+	    {
+	        internal LegacyStartupHandlerResolver(IEnumerable<Type> legacyStartupHandlers)
+                : base(legacyStartupHandlers)
+	        {
+
+	        }
+
+            public IEnumerable<IApplicationStartupHandler> LegacyStartupHandlers
+            {
+                get { return Values; }
+            }
+	    }
+
 	}
 }
\ No newline at end of file
diff --git a/src/Umbraco.Web.UI/config/umbracoSettings.Release.config b/src/Umbraco.Web.UI/config/umbracoSettings.Release.config
index d3eb0e2477..9f24056dd3 100644
--- a/src/Umbraco.Web.UI/config/umbracoSettings.Release.config
+++ b/src/Umbraco.Web.UI/config/umbracoSettings.Release.config
@@ -254,4 +254,17 @@
     trySkipIisCustomErrors="false">
   </web.routing>
 
+  <!-- 
+    web.routing
+      @trySkipIisCustomErrors
+        Tries to skip IIS custom errors.
+        Starting with IIS 7.5, this must be set to true for Umbraco 404 pages to show. Else, IIS will take
+        over and render its build-in error page. See MS doc for HttpResponseBase.TrySkipIisCustomErrors.
+        The default value is false, for backward compatibility reasons, which means that IIS _will_ take
+        over, and _prevent_ Umbraco 404 pages to show.
+  -->
+  <web.routing
+    trySkipIisCustomErrors="false">
+  </web.routing>
+
 </settings>
diff --git a/src/Umbraco.Web/WebBootManager.cs b/src/Umbraco.Web/WebBootManager.cs
index 25c6d6fc16..9e130e8fe9 100644
--- a/src/Umbraco.Web/WebBootManager.cs
+++ b/src/Umbraco.Web/WebBootManager.cs
@@ -101,6 +101,9 @@ namespace Umbraco.Web
 
             base.Complete(afterComplete);
 
+            //Now, startup all of our legacy startup handler
+            ApplicationEventsResolver.Current.InstantiateLegacyStartupHanlders();
+
             return this;
         }