diff --git a/src/Hosting/Hosting/src/GenericHost/GenericWebHostBuilder.cs b/src/Hosting/Hosting/src/GenericHost/GenericWebHostBuilder.cs
index 788995b320..a42e5cbf48 100644
--- a/src/Hosting/Hosting/src/GenericHost/GenericWebHostBuilder.cs
+++ b/src/Hosting/Hosting/src/GenericHost/GenericWebHostBuilder.cs
@@ -55,15 +55,6 @@ namespace Microsoft.AspNetCore.Hosting.Internal
                 }
             });
 
-            _builder.ConfigureServices((context, services) =>
-            {
-                if (_hostingStartupWebHostBuilder != null)
-                {
-                    var webhostContext = GetWebHostBuilderContext(context);
-                    _hostingStartupWebHostBuilder.ConfigureServices(webhostContext, services);
-                }
-            });
-
             _builder.ConfigureServices((context, services) =>
             {
                 var webhostContext = GetWebHostBuilderContext(context);
@@ -96,6 +87,9 @@ namespace Microsoft.AspNetCore.Hosting.Internal
                 services.TryAddScoped<IMiddlewareFactory, MiddlewareFactory>();
                 services.TryAddSingleton<IApplicationBuilderFactory, ApplicationBuilderFactory>();
 
+                // IMPORTANT: This needs to run *before* direct calls on the builder (like UseStartup)
+                _hostingStartupWebHostBuilder?.ConfigureServices(webhostContext, services);
+
                 // Support UseStartup(assemblyName)
                 if (!string.IsNullOrEmpty(webHostOptions.StartupAssembly))
                 {
diff --git a/src/Hosting/Hosting/test/WebHostBuilderTests.cs b/src/Hosting/Hosting/test/WebHostBuilderTests.cs
index 0c962c5848..4db65a21d9 100644
--- a/src/Hosting/Hosting/test/WebHostBuilderTests.cs
+++ b/src/Hosting/Hosting/test/WebHostBuilderTests.cs
@@ -1472,6 +1472,19 @@ namespace Microsoft.AspNetCore.Hosting
                 var loggerProvider = new TestLoggerProvider();
                 builder.UseSetting("testhostingstartup", "0")
                        .UseSetting("testhostingstartup_chain", builder.GetSetting("testhostingstartup_chain") + "0")
+                       .ConfigureServices(services =>
+                       {
+                           // This check is required because MVC still uses the
+                           // IWebHostEnvironment instance before the container is baked
+#pragma warning disable CS0618 // Type or member is obsolete
+                           var heDescriptor = services.SingleOrDefault(s => s.ServiceType == typeof(IHostingEnvironment));
+                           Assert.NotNull(heDescriptor);
+                           Assert.NotNull(heDescriptor.ImplementationInstance);
+#pragma warning restore CS0618 // Type or member is obsolete
+                           var wheDescriptor = services.SingleOrDefault(s => s.ServiceType == typeof(IWebHostEnvironment));
+                           Assert.NotNull(wheDescriptor);
+                           Assert.NotNull(wheDescriptor.ImplementationInstance);
+                       })
                        .ConfigureServices(services => services.AddSingleton<ServiceA>())
                        .ConfigureServices(services => services.AddSingleton<ITestSink>(loggerProvider.Sink))
                        .ConfigureLogging((_, lf) => lf.AddProvider(loggerProvider))