diff --git a/src/Umbraco.Core/Configuration/Models/WebRoutingSettings.cs b/src/Umbraco.Core/Configuration/Models/WebRoutingSettings.cs
index 9f06046452..d94fdd8496 100644
--- a/src/Umbraco.Core/Configuration/Models/WebRoutingSettings.cs
+++ b/src/Umbraco.Core/Configuration/Models/WebRoutingSettings.cs
@@ -10,6 +10,17 @@ namespace Umbraco.Core.Configuration.Models
     /// </summary>
     public class WebRoutingSettings
     {
+        /// <summary>
+        /// Gets or sets a value indicating whether to check if any routed endpoints match a front-end request before
+        /// the Umbraco dynamic router tries to map the request to an Umbraco content item.
+        /// </summary>
+        /// <remarks>
+        /// This should not be necessary if the Umbraco catch-all/dynamic route is registered last like it's supposed to be. In that case
+        /// ASP.NET Core will automatically handle this in all cases. This is more of a backward compatible option since this is what v7/v8 used
+        /// to do.
+        /// </remarks>
+        public bool TryMatchingEndpointsForAllPages { get; set; } = false;
+
         /// <summary>
         /// Gets or sets a value indicating whether IIS custom errors should be skipped.
         /// </summary>
diff --git a/src/Umbraco.Core/Routing/UmbracoRequestPaths.cs b/src/Umbraco.Core/Routing/UmbracoRequestPaths.cs
index 6fa3328014..e670930691 100644
--- a/src/Umbraco.Core/Routing/UmbracoRequestPaths.cs
+++ b/src/Umbraco.Core/Routing/UmbracoRequestPaths.cs
@@ -112,7 +112,6 @@ namespace Umbraco.Core.Routing
             }
 
             // check for special front-end paths
-            // TODO: These should be constants - will need to update when we do front-end routing
             if (urlPath.InvariantStartsWith(_surfaceMvcPath)
                 || urlPath.InvariantStartsWith(_apiMvcPath))
             {
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Web.Common/Routing/RoutableDocumentFilterTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Web.Common/Routing/RoutableDocumentFilterTests.cs
index b25da2351b..1c9cbc9c26 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Web.Common/Routing/RoutableDocumentFilterTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Web.Common/Routing/RoutableDocumentFilterTests.cs
@@ -18,6 +18,8 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
     {
         private IOptions<GlobalSettings> GetGlobalSettings() => Options.Create(new GlobalSettings());
 
+        private IOptions<WebRoutingSettings> GetWebRoutingSettings() => Options.Create(new WebRoutingSettings());
+
         private IHostingEnvironment GetHostingEnvironment()
         {
             var hostingEnv = new Mock<IHostingEnvironment>();
@@ -35,6 +37,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
         {
             var routableDocFilter = new RoutableDocumentFilter(
                 GetGlobalSettings(),
+                GetWebRoutingSettings(),
                 GetHostingEnvironment(),
                 new DefaultEndpointDataSource());
 
@@ -44,14 +47,14 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
 
         [TestCase("/base/somebasehandler")]
         [TestCase("/")]
-        [TestCase("/home.aspx")]
+        [TestCase("/home")]
         [TestCase("/umbraco-test")]
         [TestCase("/install-test")]
-        [TestCase("/install.aspx")]
         public void Is_Not_Reserved_Path_Or_Url(string url)
         {
             var routableDocFilter = new RoutableDocumentFilter(
                 GetGlobalSettings(),
+                GetWebRoutingSettings(),
                 GetHostingEnvironment(),
                 new DefaultEndpointDataSource());
 
@@ -73,6 +76,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
         public void Is_Reserved_By_Route(string url, bool isReserved)
         {
             var globalSettings = new GlobalSettings { ReservedPaths = string.Empty, ReservedUrls = string.Empty };
+            var routingSettings = new WebRoutingSettings { TryMatchingEndpointsForAllPages = true };
 
             RouteEndpoint endpoint1 = CreateEndpoint(
                 "Umbraco/RenderMvc/{action?}/{id?}",
@@ -88,6 +92,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
 
             var routableDocFilter = new RoutableDocumentFilter(
                 Options.Create(globalSettings),
+                Options.Create(routingSettings),
                 GetHostingEnvironment(),
                 endpointDataSource);
 
@@ -105,16 +110,18 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Web.Common.Routing
         public void Is_Reserved_By_Default_Back_Office_Route(string url, bool isReserved)
         {
             var globalSettings = new GlobalSettings { ReservedPaths = string.Empty, ReservedUrls = string.Empty };
+            var routingSettings = new WebRoutingSettings { TryMatchingEndpointsForAllPages = true };
 
             RouteEndpoint endpoint1 = CreateEndpoint(
-                "umbraco/{action}/{id?}",
-                new { controller = "BackOffice", action = "Default" },
+                "umbraco/{action?}/{id?}",
+                new { controller = "BackOffice" },
                 0);
 
             var endpointDataSource = new DefaultEndpointDataSource(endpoint1);
 
             var routableDocFilter = new RoutableDocumentFilter(
                 Options.Create(globalSettings),
+                Options.Create(routingSettings),
                 GetHostingEnvironment(),
                 endpointDataSource);
 
diff --git a/src/Umbraco.Web.Common/Routing/RoutableDocumentFilter.cs b/src/Umbraco.Web.Common/Routing/RoutableDocumentFilter.cs
index 8f61918121..dee90bbfba 100644
--- a/src/Umbraco.Web.Common/Routing/RoutableDocumentFilter.cs
+++ b/src/Umbraco.Web.Common/Routing/RoutableDocumentFilter.cs
@@ -24,6 +24,7 @@ namespace Umbraco.Web.Common.Routing
     {
         private readonly ConcurrentDictionary<string, bool> _routeChecks = new ConcurrentDictionary<string, bool>(StringComparer.OrdinalIgnoreCase);
         private readonly GlobalSettings _globalSettings;
+        private readonly WebRoutingSettings _routingSettings;
         private readonly IHostingEnvironment _hostingEnvironment;
         private readonly EndpointDataSource _endpointDataSource;
         private readonly object _routeLocker = new object();
@@ -34,9 +35,10 @@ namespace Umbraco.Web.Common.Routing
         /// <summary>
         /// Initializes a new instance of the <see cref="RoutableDocumentFilter"/> class.
         /// </summary>
-        public RoutableDocumentFilter(IOptions<GlobalSettings> globalSettings, IHostingEnvironment hostingEnvironment, EndpointDataSource endpointDataSource)
+        public RoutableDocumentFilter(IOptions<GlobalSettings> globalSettings, IOptions<WebRoutingSettings> routingSettings, IHostingEnvironment hostingEnvironment, EndpointDataSource endpointDataSource)
         {
             _globalSettings = globalSettings.Value;
+            _routingSettings = routingSettings.Value;
             _hostingEnvironment = hostingEnvironment;
             _endpointDataSource = endpointDataSource;
             _endpointDataSource.GetChangeToken().RegisterChangeCallback(EndpointsChanged, null);
@@ -67,20 +69,17 @@ namespace Umbraco.Web.Common.Routing
             // a document request should be
             // /foo/bar/nil
             // /foo/bar/nil/
-            // /foo/bar/nil.aspx
             // where /foo is not a reserved path
 
-            // TODO: Remove aspx checks
-
-            // if the path contains an extension that is not .aspx
+            // if the path contains an extension 
             // then it cannot be a document request
             var extension = Path.GetExtension(absPath);
-            if (maybeDoc && extension.IsNullOrWhiteSpace() == false && !extension.InvariantEquals(".aspx"))
+            if (maybeDoc && !extension.IsNullOrWhiteSpace())
             {
                 maybeDoc = false;
             }
 
-            // at that point, either we have no extension, or it is .aspx
+            // at that point we have no extension
 
             // if the path is reserved then it cannot be a document request
             if (maybeDoc && IsReservedPathOrUrl(absPath))
@@ -143,16 +142,9 @@ namespace Umbraco.Web.Common.Routing
                 return true;
             }
 
-            // TODO: We have a problem here:
-            // For every page that is rendered we are storing the URL and if it's routable in _routeChecks which
-            // is a small memory leak. Not sure how we work around this since routes are all dynamic and we don't want
-            // to double route everything on each request. Maybe instead of a growing list it's a list with a max capacity?
-            // BUT... then do we need to do this at all? So long as the catch all route is registered LAST shouldn't all other routes
-            // just match before it anyways and then we don't need to check? The strange part is that the "/umbraco" route doesn't automatically
-            // match so we need to investigate that first. 
-
-            // check if the current request matches a route, if so then it is reserved.
-            var hasRoute = _routeChecks.GetOrAdd(absPath, x => MatchesEndpoint(absPath));
+            // If configured, check if the current request matches a route, if so then it is reserved,
+            // else if not configured (default) proceed as normal since we assume the request is for an Umbraco content item.
+            var hasRoute = _routingSettings.TryMatchingEndpointsForAllPages && _routeChecks.GetOrAdd(absPath, x => MatchesEndpoint(absPath));
             if (hasRoute)
             {
                 return true;