diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AspNetCore.vcxproj b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AspNetCore.vcxproj
index d53a438f03..db33b281cd 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AspNetCore.vcxproj
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AspNetCore.vcxproj
@@ -233,8 +233,6 @@
     <ClInclude Include="AppOfflineApplication.h" />
     <ClInclude Include="AppOfflineHandler.h" />
     <ClInclude Include="DisconnectHandler.h" />
-    <ClInclude Include="PollingAppOfflineApplication.h" />
-    <ClInclude Include="ServerErrorApplication.h" />
     <ClInclude Include="ShimOptions.h" />
     <ClInclude Include="globalmodule.h" />
     <ClInclude Include="resource.h" />
@@ -249,7 +247,6 @@
     <ClCompile Include="AppOfflineApplication.cpp" />
     <ClCompile Include="AppOfflineHandler.cpp" />
     <ClCompile Include="DisconnectHandler.cpp" />
-    <ClCompile Include="PollingAppOfflineApplication.cpp" />
     <ClCompile Include="ShimOptions.cpp" />
     <ClCompile Include="dllmain.cpp" />
     <ClCompile Include="globalmodule.cpp" />
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
index 8491edc5a4..cb4893196f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
@@ -28,7 +28,10 @@ HandlerResolver::HandlerResolver(HMODULE hModule, const IHttpServer &pServer)
 }
 
 HRESULT
-HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication, const ShimOptions& pConfiguration, std::unique_ptr<ApplicationFactory>& pApplicationFactory)
+HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication,
+    const ShimOptions& pConfiguration,
+    std::unique_ptr<ApplicationFactory>& pApplicationFactory,
+    ErrorContext& errorContext)
 {
     HRESULT hr = S_OK;
     PCWSTR pstrHandlerDllName = nullptr;
@@ -53,6 +56,7 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
     {
         if (pConfiguration.QueryHostingModel() == APP_HOSTING_MODEL::HOSTING_IN_PROCESS)
         {
+            errorContext.generalErrorType = "ANCM In-Process Handler Load Failure";
             std::unique_ptr<HostFxrResolutionResult> options;
 
             RETURN_IF_FAILED(HostFxrResolutionResult::Create(
@@ -66,12 +70,12 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
 
             auto redirectionOutput = std::make_shared<StringStreamRedirectionOutput>();
 
-            hr = FindNativeAssemblyFromHostfxr(*options, pstrHandlerDllName, handlerDllPath, pApplication, pConfiguration, redirectionOutput);
+            hr = FindNativeAssemblyFromHostfxr(*options, pstrHandlerDllName, handlerDllPath, pApplication, pConfiguration, redirectionOutput, errorContext);
+
+            auto output = redirectionOutput->GetOutput();
 
             if (FAILED_LOG(hr))
             {
-                auto output = redirectionOutput->GetOutput();
-
                 EventLog::Error(
                     ASPNETCORE_EVENT_GENERAL_ERROR,
                     ASPNETCORE_EVENT_INPROCESS_RH_ERROR_MSG,
@@ -81,12 +85,20 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
         }
         else
         {
+            errorContext.generalErrorType = "ANCM Out-Of-Process Handler Load Failure";
+
             if (FAILED_LOG(hr = FindNativeAssemblyFromGlobalLocation(pConfiguration, pstrHandlerDllName, handlerDllPath)))
             {
+                auto handlerName = handlerDllPath.empty() ? s_pwzAspnetcoreOutOfProcessRequestHandlerName : handlerDllPath.c_str();
                 EventLog::Error(
                     ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING,
                     ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING_MSG,
-                    handlerDllPath.empty() ? s_pwzAspnetcoreOutOfProcessRequestHandlerName : handlerDllPath.c_str());
+                    handlerName);
+
+                errorContext.detailedErrorContent = to_multi_byte_string(format(ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING_MSG, handlerName), CP_UTF8);
+                errorContext.statusCode = 500i16;
+                errorContext.subStatusCode = 36i16;
+                errorContext.errorReason = "The out of process request handler, aspnetcorev2_outofprocess.dll, could not be found next to the aspnetcorev2.dll.";
 
                 return hr;
             }
@@ -96,6 +108,7 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
 
         hRequestHandlerDll = LoadLibrary(handlerDllPath.c_str());
         RETURN_LAST_ERROR_IF_NULL(hRequestHandlerDll);
+
         if (preventUnload)
         {
             // Pin module in memory
@@ -111,7 +124,7 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
 }
 
 HRESULT
-HandlerResolver::GetApplicationFactory(const IHttpApplication &pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options)
+HandlerResolver::GetApplicationFactory(const IHttpApplication& pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext)
 {
     SRWExclusiveLock lock(m_requestHandlerLoadLock);
     if (m_loadedApplicationHostingModel != HOSTING_UNKNOWN)
@@ -119,6 +132,12 @@ HandlerResolver::GetApplicationFactory(const IHttpApplication &pApplication, std
         // Mixed hosting models
         if (m_loadedApplicationHostingModel != options.QueryHostingModel())
         {
+            errorContext.detailedErrorContent = to_multi_byte_string(format(ASPNETCORE_EVENT_MIXED_HOSTING_MODEL_ERROR_MSG, pApplication.GetApplicationId(), options.QueryHostingModel()), CP_UTF8);
+            errorContext.statusCode = 500i16;
+            errorContext.subStatusCode = 34i16;
+            errorContext.generalErrorType = "ANCM Mixed Hosting Models Not Supported";
+            errorContext.errorReason = "Select a different application pool to create another application.";
+
             EventLog::Error(
                 ASPNETCORE_EVENT_MIXED_HOSTING_MODEL_ERROR,
                 ASPNETCORE_EVENT_MIXED_HOSTING_MODEL_ERROR_MSG,
@@ -130,6 +149,13 @@ HandlerResolver::GetApplicationFactory(const IHttpApplication &pApplication, std
         // Multiple in-process apps
         if (m_loadedApplicationHostingModel == HOSTING_IN_PROCESS && m_loadedApplicationId != pApplication.GetApplicationId())
         {
+            errorContext.detailedErrorContent = to_multi_byte_string(format(ASPNETCORE_EVENT_DUPLICATED_INPROCESS_APP_MSG, pApplication.GetApplicationId()), CP_UTF8);
+
+            errorContext.statusCode = 500i16;
+            errorContext.subStatusCode = 35i16;
+            errorContext.generalErrorType = "ANCM Multiple In-Process Applications in same Process";
+            errorContext.errorReason = "Select a different application pool to create another in-process application.";
+
             EventLog::Error(
                 ASPNETCORE_EVENT_DUPLICATED_INPROCESS_APP,
                 ASPNETCORE_EVENT_DUPLICATED_INPROCESS_APP_MSG,
@@ -141,7 +167,7 @@ HandlerResolver::GetApplicationFactory(const IHttpApplication &pApplication, std
 
     m_loadedApplicationHostingModel = options.QueryHostingModel();
     m_loadedApplicationId = pApplication.GetApplicationId();
-    RETURN_IF_FAILED(LoadRequestHandlerAssembly(pApplication, options, pApplicationFactory));
+    RETURN_IF_FAILED(LoadRequestHandlerAssembly(pApplication, options, pApplicationFactory, errorContext));
 
     return S_OK;
 }
@@ -181,7 +207,7 @@ HandlerResolver::FindNativeAssemblyFromGlobalLocation(
     }
     catch (...)
     {
-       EventLog::Info(
+        EventLog::Info(
                 ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING,
                 ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING_MSG,
                 pstrHandlerDllName);
@@ -204,7 +230,8 @@ HandlerResolver::FindNativeAssemblyFromHostfxr(
     std::wstring& handlerDllPath,
     const IHttpApplication &pApplication,
     const ShimOptions& pConfiguration,
-    std::shared_ptr<RedirectionOutput> stringRedirectionOutput
+    std::shared_ptr<StringStreamRedirectionOutput> stringRedirectionOutput,
+    ErrorContext& errorContext
 )
 try
 {
@@ -214,14 +241,25 @@ try
     DWORD          dwBufferSize = s_initialGetNativeSearchDirectoriesBufferSize;
     DWORD          dwRequiredBufferSize = 0;
 
-    m_hHostFxrDll.Load(hostfxrOptions.GetHostFxrLocation());
-
+    try
+    {
+        m_hHostFxrDll.Load(hostfxrOptions.GetHostFxrLocation());
+    }
+    catch (...)
+    {
+        errorContext.detailedErrorContent = "Could not load hostfxr.dll.";
+        errorContext.statusCode = 500i16;
+        errorContext.subStatusCode = 32i16;
+        errorContext.generalErrorType = "ANCM Failed to Load dll";
+        errorContext.errorReason = "The application was likely published for a different bitness than w3wp.exe/iisexpress.exe is running as.";
+        throw;
+    }
     {
         auto redirectionOutput = LoggingHelpers::CreateOutputs(
                 pConfiguration.QueryStdoutLogEnabled(),
                 pConfiguration.QueryStdoutLogFile(),
                 pApplication.GetApplicationPhysicalPath(),
-                std::move(stringRedirectionOutput)
+                stringRedirectionOutput
             );
 
         StandardStreamRedirection stdOutRedirection(*redirectionOutput.get(), m_pServer.IsCommandLineLaunch());
@@ -256,7 +294,16 @@ try
             else
             {
                 // If hostfxr didn't set the required buffer size, something in the app is misconfigured
-                // Ex: Framework not found.
+                // This like almost always is framework not found.
+                auto output = to_multi_byte_string(stringRedirectionOutput->GetOutput(), CP_UTF8);
+                errorContext.detailedErrorContent.resize(output.length());
+                memcpy(&errorContext.detailedErrorContent[0], output.c_str(), output.length());
+
+                errorContext.statusCode = 500i16;
+                errorContext.subStatusCode = 31i16;
+                errorContext.generalErrorType = "ANCM Failed to Find Native Dependencies";
+                errorContext.errorReason = "The specified version of Microsoft.NetCore.App or Microsoft.AspNetCore.App was not found.";
+
                 EventLog::Error(
                     ASPNETCORE_EVENT_GENERAL_ERROR,
                     ASPNETCORE_EVENT_HOSTFXR_FAILURE_MSG
@@ -296,6 +343,16 @@ try
 
     if (!fFound)
     {
+        // This only occurs if the request handler isn't referenced by the app, which rarely happens if they are targeting the shared framework.
+        errorContext.statusCode = 500i16;
+        errorContext.subStatusCode = 33i16;
+        errorContext.generalErrorType = "ANCM Request Handler Load Failure";
+        errorContext.detailedErrorContent = to_multi_byte_string(format(ASPNETCORE_EVENT_INPROCESS_RH_REFERENCE_MSG, handlerDllPath.empty()
+                ? s_pwzAspnetcoreInProcessRequestHandlerName
+                : handlerDllPath.c_str()),
+            CP_UTF8);
+        errorContext.errorReason = "Make sure Microsoft.AspNetCore.App is referenced by your application.";
+
         EventLog::Error(
             ASPNETCORE_EVENT_GENERAL_ERROR,
             ASPNETCORE_EVENT_INPROCESS_RH_REFERENCE_MSG,
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
index faa81855c3..9ab017bb50 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
@@ -16,11 +16,11 @@ class HandlerResolver
 {
 public:
     HandlerResolver(HMODULE hModule, const IHttpServer &pServer);
-    HRESULT GetApplicationFactory(const IHttpApplication &pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options);
+    HRESULT GetApplicationFactory(const IHttpApplication &pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext);
     void ResetHostingModel();
 
 private:
-    HRESULT LoadRequestHandlerAssembly(const IHttpApplication &pApplication, const ShimOptions& pConfiguration, std::unique_ptr<ApplicationFactory>& pApplicationFactory);
+    HRESULT LoadRequestHandlerAssembly(const IHttpApplication &pApplication, const ShimOptions& pConfiguration, std::unique_ptr<ApplicationFactory>& pApplicationFactory, ErrorContext& errorContext);
     HRESULT FindNativeAssemblyFromGlobalLocation(const ShimOptions& pConfiguration, PCWSTR libraryName, std::wstring& handlerDllPath);
     HRESULT FindNativeAssemblyFromHostfxr(
         const HostFxrResolutionResult& hostfxrOptions,
@@ -28,7 +28,8 @@ private:
         std::wstring& handlerDllPath,
         const IHttpApplication &pApplication,
         const ShimOptions& pConfiguration,
-        std::shared_ptr<RedirectionOutput> stringRedirectionOutput);
+        std::shared_ptr<StringStreamRedirectionOutput> stringRedirectionOutput,
+        ErrorContext& errorContext);
 
     HMODULE m_hModule;
     const IHttpServer &m_pServer;
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/InProcessShimStaticHtml.htm b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/InProcessShimStaticHtml.htm
index a8c9d7fe1f..a9e6d96c75 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/InProcessShimStaticHtml.htm
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/InProcessShimStaticHtml.htm
@@ -2,7 +2,7 @@
 <html lang="en-US" xmlns="http://www.w3.org/1999/xhtml">
     <head>
         <meta charset="utf-8" />
-        <title> HTTP Error 500.0 - ANCM In-Process Handler Load Failure </title>
+        <title> HTTP Error %d.%d - %s </title>
         <style>
             body {
                 font-family: 'Segoe UI', Tahoma, Arial, Helvetica, sans-serif;
@@ -58,15 +58,11 @@
         </style>
     </head>
     <body>
-        <h1> HTTP Error 500.0 - ANCM In-Process Handler Load Failure </h1>
+        <h1> HTTP Error %d.%d - %s </h1>
 
-        <h2> Common causes of this issue: </h2>
+        %s
 
-        <ul>
-            <li> The specified version of Microsoft.NetCore.App or Microsoft.AspNetCore.App was not found. </li>
-            <li> The in process request handler, Microsoft.AspNetCore.Server.IIS, was not referenced in the application. </li>
-            <li> ANCM could not find dotnet. </li>
-        </ul>
+        %s
 
         <h2> Troubleshooting steps: </h2>
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/OutOfProcessShimStaticHtml.htm b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/OutOfProcessShimStaticHtml.htm
index 1194cf4025..b15ed7dccb 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/OutOfProcessShimStaticHtml.htm
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/OutOfProcessShimStaticHtml.htm
@@ -2,7 +2,7 @@
 <html lang="en-US" xmlns="http://www.w3.org/1999/xhtml">
     <head>
         <meta charset="utf-8" />
-        <title> HTTP Error 500.0 - ANCM Out-Of-Process Handler Load Failure </title>
+        <title> HTTP Error %d.%d - %s </title>
         <style>
             body {
                 font-family: 'Segoe UI', Tahoma, Arial, Helvetica, sans-serif;
@@ -58,13 +58,11 @@
         </style>
     </head>
     <body>
-        <h1> HTTP Error 500.0 - ANCM Out-Of-Process Handler Load Failure </h1>
+        <h1> HTTP Error %d.%d - %s </h1>
 
-        <h2> Common causes of this issue: </h2>
-        <ul>
-            <li>The out of process request handler, aspnetcorev2_outofprocess.dll, could not be found next to the aspnetcorev2.dll.</li>
-            <li> Could not read configuration correctly. Check the application's associated web.config.</li>
-        </ul>
+        %s
+
+        %s
 
         <h2> Troubleshooting steps: </h2>
         <ul>
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
index cb7f1488d7..fa1282cdb6 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
@@ -5,6 +5,7 @@
 
 #include "StringHelpers.h"
 #include "ConfigurationLoadException.h"
+#include "Environment.h"
 
 #define CS_ASPNETCORE_HANDLER_VERSION                    L"handlerVersion"
 
@@ -41,4 +42,16 @@ ShimOptions::ShimOptions(const ConfigurationSource &configurationSource) :
     m_fStdoutLogEnabled = section->GetRequiredBool(CS_ASPNETCORE_STDOUT_LOG_ENABLED);
     m_struStdoutLogFile = section->GetRequiredString(CS_ASPNETCORE_STDOUT_LOG_FILE);
     m_fDisableStartupPage = section->GetRequiredBool(CS_ASPNETCORE_DISABLE_START_UP_ERROR_PAGE);
+
+    // This will not include environment variables defined in the web.config.
+    // Reading environment variables can be added here, but it adds more code to the shim.
+    const auto detailedErrors = Environment::GetEnvironmentVariableValue(L"ASPNETCORE_DETAILEDERRORS").value_or(L"");
+    const auto aspnetCoreEnvironment = Environment::GetEnvironmentVariableValue(L"ASPNETCORE_ENVIRONMENT").value_or(L"");
+    const auto dotnetEnvironment = Environment::GetEnvironmentVariableValue(L"DOTNET_ENVIRONMENT").value_or(L"");
+
+    auto detailedErrorsEnabled = equals_ignore_case(L"1", detailedErrors) || equals_ignore_case(L"true", detailedErrors);
+    auto aspnetCoreEnvironmentEnabled = equals_ignore_case(L"Development", aspnetCoreEnvironment);
+    auto dotnetEnvironmentEnabled = equals_ignore_case(L"Development", dotnetEnvironment);
+
+    m_fShowDetailedErrors = detailedErrorsEnabled || aspnetCoreEnvironmentEnabled || dotnetEnvironmentEnabled;
 }
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
index 3cfb47169e..5d1c04f8ab 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
@@ -59,6 +59,12 @@ public:
         return m_fDisableStartupPage;
     }
 
+    bool
+    QueryShowDetailedErrors() const noexcept
+    {
+        return m_fShowDetailedErrors;
+    }
+
     ShimOptions(const ConfigurationSource &configurationSource);
 
 private:
@@ -69,4 +75,5 @@ private:
     std::wstring                   m_struStdoutLogFile;
     bool                           m_fStdoutLogEnabled;
     bool                           m_fDisableStartupPage;
+    bool                           m_fShowDetailedErrors;
 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
index 317a8a5d4b..a0a6bfeb3b 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
@@ -15,6 +15,7 @@
 #include "WebConfigConfigurationSource.h"
 #include "ConfigurationLoadException.h"
 #include "resource.h"
+#include "file_utility.h"
 
 extern HINSTANCE           g_hServerModule;
 
@@ -86,23 +87,39 @@ APPLICATION_INFO::CreateApplication(IHttpContext& pHttpContext)
             const WebConfigConfigurationSource configurationSource(m_pServer.GetAdminManager(), pHttpApplication);
             ShimOptions options(configurationSource);
 
-            const auto hr = TryCreateApplication(pHttpContext, options);
+            ErrorContext errorContext;
+            errorContext.statusCode = 500i16;
+            errorContext.subStatusCode = 0i16;
+
+            const auto hr = TryCreateApplication(pHttpContext, options, errorContext);
 
             if (FAILED_LOG(hr))
             {
-                // Log the failure and update application info to not try again
                 EventLog::Error(
                     ASPNETCORE_EVENT_ADD_APPLICATION_ERROR,
                     ASPNETCORE_EVENT_ADD_APPLICATION_ERROR_MSG,
                     pHttpApplication.GetApplicationId(),
                     hr);
 
+                auto page = options.QueryHostingModel() == APP_HOSTING_MODEL::HOSTING_IN_PROCESS ? IN_PROCESS_SHIM_STATIC_HTML : OUT_OF_PROCESS_SHIM_STATIC_HTML;
+                std::string responseContent;
+                if (options.QueryShowDetailedErrors())
+                {
+                    responseContent = FILE_UTILITY::GetHtml(g_hServerModule, page, errorContext.statusCode, errorContext.subStatusCode, errorContext.generalErrorType, errorContext.errorReason, errorContext.detailedErrorContent);
+                }
+                else
+                {
+                    responseContent = FILE_UTILITY::GetHtml(g_hServerModule, page, errorContext.statusCode, errorContext.subStatusCode, errorContext.generalErrorType, errorContext.errorReason);
+                }
+
                 m_pApplication = make_application<ServerErrorApplication>(
                     pHttpApplication,
                     hr,
-                    g_hServerModule,
                     options.QueryDisableStartupPage(),
-                    options.QueryHostingModel() == APP_HOSTING_MODEL::HOSTING_IN_PROCESS ? IN_PROCESS_SHIM_STATIC_HTML : OUT_OF_PROCESS_SHIM_STATIC_HTML);
+                    responseContent,
+                    errorContext.statusCode,
+                    errorContext.subStatusCode,
+                    "Internal Server Error");
             }
             return S_OK;
         }
@@ -124,14 +141,18 @@ APPLICATION_INFO::CreateApplication(IHttpContext& pHttpContext)
         m_pApplication = make_application<ServerErrorApplication>(
             pHttpApplication,
             E_FAIL,
-            g_hServerModule);
+            false /* disableStartupPage */,
+            "" /* responseContent */,
+            500i16 /* statusCode */,
+            0i16 /* subStatusCode */,
+            "Internal Server Error");
 
         return S_OK;
     }
 }
 
 HRESULT
-APPLICATION_INFO::TryCreateApplication(IHttpContext& pHttpContext, const ShimOptions& options)
+APPLICATION_INFO::TryCreateApplication(IHttpContext& pHttpContext, const ShimOptions& options, ErrorContext& error)
 {
     const auto startupEvent = Environment::GetEnvironmentVariableValue(L"ASPNETCORE_STARTUP_SUSPEND_EVENT");
     if (startupEvent.has_value())
@@ -157,7 +178,7 @@ APPLICATION_INFO::TryCreateApplication(IHttpContext& pHttpContext, const ShimOpt
         }
     }
 
-    RETURN_IF_FAILED(m_handlerResolver.GetApplicationFactory(*pHttpContext.GetApplication(), m_pApplicationFactory, options));
+    RETURN_IF_FAILED(m_handlerResolver.GetApplicationFactory(*pHttpContext.GetApplication(), m_pApplicationFactory, options, error));
     LOG_INFO(L"Creating handler application");
 
     IAPPLICATION * newApplication;
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
index 252d4e0d2d..f90b0588d9 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
@@ -77,7 +77,7 @@ private:
     CreateApplication(IHttpContext& pHttpContext);
 
     HRESULT
-    TryCreateApplication(IHttpContext& pHttpContext, const ShimOptions& options);
+    TryCreateApplication(IHttpContext& pHttpContext, const ShimOptions& options, ErrorContext& error);
 
     IHttpServer            &m_pServer;
     HandlerResolver        &m_handlerResolver;
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/CommonLib.vcxproj b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/CommonLib.vcxproj
index fc02995961..8816dafbda 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/CommonLib.vcxproj
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/CommonLib.vcxproj
@@ -196,6 +196,7 @@
     </Lib>
   </ItemDefinitionGroup>
   <ItemGroup>
+    <ClInclude Include="PollingAppOfflineApplication.h" />
     <ClInclude Include="application.h" />
     <ClInclude Include="BindingInformation.h" />
     <ClInclude Include="ConfigurationSection.h" />
@@ -220,11 +221,11 @@
     <ClInclude Include="LoggingHelpers.h" />
     <ClInclude Include="ModuleHelpers.h" />
     <ClInclude Include="NonCopyable.h" />
+    <ClInclude Include="ServerErrorApplication.h" />
     <ClInclude Include="StandardStreamRedirection.h" />
     <ClInclude Include="RegistryKey.h" />
     <ClInclude Include="requesthandler.h" />
     <ClInclude Include="resources.h" />
-    <ClInclude Include="ServerErrorApplication.h" />
     <ClInclude Include="ServerErrorHandler.h" />
     <ClInclude Include="SRWExclusiveLock.h" />
     <ClInclude Include="SRWSharedLock.h" />
@@ -249,6 +250,7 @@
     <ClCompile Include="HostFxrResolver.cpp" />
     <ClCompile Include="HostFxrResolutionResult.cpp" />
     <ClCompile Include="LoggingHelpers.cpp" />
+    <ClCompile Include="PollingAppOfflineApplication.cpp" />
     <ClCompile Include="StandardStreamRedirection.cpp" />
     <ClCompile Include="RedirectionOutput.cpp" />
     <ClCompile Include="RegistryKey.cpp" />
@@ -277,4 +279,4 @@
   <Import Project="..\..\build\native.targets" />
   <ImportGroup Label="ExtensionTargets">
   </ImportGroup>
-</Project>
+</Project>
\ No newline at end of file
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
index be6484e16b..118a67198b 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
@@ -45,6 +45,13 @@ Environment::GetEnvironmentVariableValue(const std::wstring & str)
 
         throw std::system_error(GetLastError(), std::system_category(), "GetEnvironmentVariableW");
     }
+    else if (requestedSize == 1)
+    {
+        // String just contains a nullcharacter, return empty string
+        // GetEnvironmentVariableW has inconsistent behavior when returning size for an empty
+        // environment variable.
+        return L"";
+    }
 
     std::wstring expandedStr;
     do
@@ -53,6 +60,10 @@ Environment::GetEnvironmentVariableValue(const std::wstring & str)
         requestedSize = GetEnvironmentVariableW(str.c_str(), expandedStr.data(), requestedSize);
         if (requestedSize == 0)
         {
+            if (GetLastError() == ERROR_ENVVAR_NOT_FOUND)
+            {
+                return std::nullopt;
+            }
             throw std::system_error(GetLastError(), std::system_category(), "ExpandEnvironmentStringsW");
         }
     } while (expandedStr.size() != requestedSize + 1);
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
index 990963b6e7..85cae5b1ba 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
@@ -12,6 +12,16 @@ typedef INT(*hostfxr_main_fn) (DWORD argc, CONST PCWSTR argv[]);
 typedef void(*corehost_error_writer_fn) (const WCHAR* message);
 typedef corehost_error_writer_fn(*corehost_set_error_writer_fn) (corehost_error_writer_fn error_writer);
 
+struct ErrorContext
+{
+    // TODO consider adding HRESULT here
+    std::string detailedErrorContent;
+    USHORT statusCode;
+    USHORT subStatusCode;
+    std::string generalErrorType;
+    std::string errorReason;
+};
+
 class HostFxrErrorRedirector: NonCopyable
 {
 public:
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/PollingAppOfflineApplication.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp
similarity index 100%
rename from src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/PollingAppOfflineApplication.cpp
rename to src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/PollingAppOfflineApplication.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.h
similarity index 100%
rename from src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/PollingAppOfflineApplication.h
rename to src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.h
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ServerErrorApplication.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorApplication.h
similarity index 58%
rename from src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ServerErrorApplication.h
rename to src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorApplication.h
index b5b86aa20c..6cb0cd9342 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ServerErrorApplication.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorApplication.h
@@ -9,16 +9,13 @@
 class ServerErrorApplication : public PollingAppOfflineApplication
 {
 public:
-    ServerErrorApplication(const IHttpApplication& pApplication, HRESULT hr, HINSTANCE moduleInstance)
-        : ServerErrorApplication(pApplication, hr, moduleInstance, true /* disableStartupPage*/, 0 /* page */)
-    {
-    }
-
-    ServerErrorApplication(const IHttpApplication& pApplication, HRESULT hr, HINSTANCE moduleInstance, bool disableStartupPage, int page)
+    ServerErrorApplication(const IHttpApplication& pApplication, HRESULT hr, bool disableStartupPage, const std::string& responseContent, USHORT status, USHORT substatus, const std::string& statusText)
         : m_HR(hr),
         m_disableStartupPage(disableStartupPage),
-        m_page(page),
-        m_moduleInstance(moduleInstance),
+        m_responseContent(responseContent),
+        m_statusCode(status),
+        m_subStatusCode(substatus),
+        m_statusText(statusText),
         PollingAppOfflineApplication(pApplication, PollingAppOfflineApplicationMode::StopWhenAdded)
     {
     }
@@ -27,8 +24,8 @@ public:
 
     HRESULT CreateHandler(IHttpContext *pHttpContext, IREQUEST_HANDLER ** pRequestHandler) override
     {
-        auto handler = std::make_unique<ServerErrorHandler>(*pHttpContext, 500ui16, 0ui16, "Internal Server Error", m_HR, m_moduleInstance, m_disableStartupPage, m_page);
-        *pRequestHandler = handler.release();
+        *pRequestHandler = std::make_unique<ServerErrorHandler>(*pHttpContext, m_statusCode, m_subStatusCode, m_statusText, m_HR, m_disableStartupPage, m_responseContent).release();
+
         return S_OK;
     }
 
@@ -36,6 +33,8 @@ public:
 private:
     HRESULT m_HR;
     bool m_disableStartupPage;
-    int m_page;
-    HINSTANCE m_moduleInstance;
+    std::string m_responseContent;
+    USHORT m_statusCode;
+    USHORT m_subStatusCode;
+    std::string m_statusText;
 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorHandler.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorHandler.h
index 3296c68c11..77d94230b2 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorHandler.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/ServerErrorHandler.h
@@ -9,44 +9,36 @@
 class ServerErrorHandler : public REQUEST_HANDLER
 {
 public:
-    ServerErrorHandler(IHttpContext& pContext, USHORT statusCode, USHORT subStatusCode, const std::string& statusText, HRESULT hr, HINSTANCE module, bool disableStartupPage, int page) noexcept
-        : ServerErrorHandler(pContext, statusCode, subStatusCode, statusText, hr, module, disableStartupPage, page, std::vector<byte>()) 
-    {
-    }
-
-    ServerErrorHandler(IHttpContext& pContext, USHORT statusCode, USHORT subStatusCode, const std::string& statusText, HRESULT hr, HINSTANCE module, bool disableStartupPage, int page, const std::vector<byte>& content) noexcept
+    ServerErrorHandler(IHttpContext& pContext, USHORT statusCode, USHORT subStatusCode, const std::string& statusText, HRESULT hr, bool disableStartupPage, std::string& responseContent) noexcept
         : REQUEST_HANDLER(pContext),
-        m_pContext(pContext),
         m_HR(hr),
         m_disableStartupPage(disableStartupPage),
         m_statusCode(statusCode),
         m_subStatusCode(subStatusCode),
         m_statusText(std::move(statusText)),
-        m_page(page),
-        m_ExceptionInfoContent(content),
-        m_moduleInstance(module)
+        m_ExceptionInfoContent(responseContent)
     {
     }
 
     REQUEST_NOTIFICATION_STATUS ExecuteRequestHandler() override
     {
-        WriteStaticResponse(m_pContext, m_HR, m_disableStartupPage);
+        WriteResponse();
 
         return RQ_NOTIFICATION_FINISH_REQUEST;
     }
 
 private:
-    void WriteStaticResponse(IHttpContext& pContext, HRESULT hr, bool disableStartupErrorPage) 
+    void WriteResponse()
     {
-        if (disableStartupErrorPage)
+        if (m_disableStartupPage)
         {
-            pContext.GetResponse()->SetStatus(m_statusCode, m_statusText.c_str(), m_subStatusCode, E_FAIL);
+            m_pHttpContext.GetResponse()->SetStatus(m_statusCode, m_statusText.c_str(), m_subStatusCode, E_FAIL);
             return;
         }
 
         HTTP_DATA_CHUNK dataChunk = {};
-        IHttpResponse* pResponse = pContext.GetResponse();
-        pResponse->SetStatus(m_statusCode, m_statusText.c_str(), m_subStatusCode, hr, nullptr, true);
+        IHttpResponse* pResponse = m_pHttpContext.GetResponse();
+        pResponse->SetStatus(m_statusCode, m_statusText.c_str(), m_subStatusCode, m_HR, nullptr, true);
         pResponse->SetHeader("Content-Type",
             "text/html",
             (USHORT)strlen("text/html"),
@@ -54,62 +46,16 @@ private:
         );
 
         dataChunk.DataChunkType = HttpDataChunkFromMemory;
-        if (m_ExceptionInfoContent.size() > 0)
-        {
-            dataChunk.FromMemory.pBuffer = &m_ExceptionInfoContent[0];
-            dataChunk.FromMemory.BufferLength = static_cast<ULONG>(m_ExceptionInfoContent.size());
-        }
-        else
-        {
-            static std::string s_html500Page = GetHtml(m_moduleInstance, m_page);
-            dataChunk.FromMemory.pBuffer = s_html500Page.data();
-            dataChunk.FromMemory.BufferLength = static_cast<ULONG>(s_html500Page.size());
-        }
-      
+        dataChunk.FromMemory.pBuffer = m_ExceptionInfoContent.data();
+        dataChunk.FromMemory.BufferLength = static_cast<ULONG>(m_ExceptionInfoContent.size());
+
         pResponse->WriteEntityChunkByReference(&dataChunk);
     }
 
-    std::string
-    GetHtml(HMODULE module, int page)
-    {
-        try
-        {
-            HRSRC rc = nullptr;
-            HGLOBAL rcData = nullptr;
-            std::string data;
-            const char* pTempData = nullptr;
-
-            THROW_LAST_ERROR_IF_NULL(rc = FindResource(module, MAKEINTRESOURCE(page), RT_HTML));
-            THROW_LAST_ERROR_IF_NULL(rcData = LoadResource(module, rc));
-            auto const size = SizeofResource(module, rc);
-            THROW_LAST_ERROR_IF(size == 0);
-            THROW_LAST_ERROR_IF_NULL(pTempData = static_cast<const char*>(LockResource(rcData)));
-            data = std::string(pTempData, size);
-
-            auto additionalErrorLink = Environment::GetEnvironmentVariableValue(L"ANCM_ADDITIONAL_ERROR_PAGE_LINK");
-            std::string additionalHtml;
-
-            if (additionalErrorLink.has_value())
-            {
-                additionalHtml = format("<a href=\"%S\"> <cite> %S </cite></a> and ", additionalErrorLink->c_str(), additionalErrorLink->c_str());
-            }
-
-            return format(data, additionalHtml.c_str());
-        }
-        catch (...)
-        {
-            OBSERVE_CAUGHT_EXCEPTION();
-            return "";
-        }
-    }
-
-    IHttpContext& m_pContext;
     HRESULT m_HR;
     bool m_disableStartupPage;
-    int m_page;
-    HINSTANCE m_moduleInstance;
     USHORT m_statusCode;
     USHORT m_subStatusCode;
     std::string m_statusText;
-    std::vector<byte> m_ExceptionInfoContent;
+    std::string& m_ExceptionInfoContent;
 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.cpp
index 2831eac64d..fb10427e3f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.cpp
@@ -6,6 +6,7 @@
 #include <Shlwapi.h>
 #include "debugutil.h"
 #include "exceptions.h"
+#include "Environment.h"
 
 HRESULT
 FILE_UTILITY::IsPathUnc(
@@ -167,3 +168,53 @@ Finished:
     return hr;
 }
 
+std::string FILE_UTILITY::GetHtml(HMODULE module, int page, USHORT statusCode, USHORT subStatusCode, const std::string& speicificReasonPhrase, const std::string& solution)
+{
+    return GetHtml(module, page, statusCode, subStatusCode, speicificReasonPhrase, solution, std::string());
+}
+
+std::string
+FILE_UTILITY::GetHtml(HMODULE module, int page, USHORT statusCode, USHORT subStatusCode, const std::string& specificReasonPhrase, const std::string& errorReason, const std::string& specificError)
+{
+    try
+    {
+        HRSRC rc = nullptr;
+        HGLOBAL rcData = nullptr;
+        std::string data;
+        const char* pTempData = nullptr;
+
+        THROW_LAST_ERROR_IF_NULL(rc = FindResource(module, MAKEINTRESOURCE(page), RT_HTML));
+        THROW_LAST_ERROR_IF_NULL(rcData = LoadResource(module, rc));
+        auto const size = SizeofResource(module, rc);
+        THROW_LAST_ERROR_IF(size == 0);
+        THROW_LAST_ERROR_IF_NULL(pTempData = static_cast<const char*>(LockResource(rcData)));
+        data = std::string(pTempData, size);
+
+        auto additionalErrorLink = Environment::GetEnvironmentVariableValue(L"ANCM_ADDITIONAL_ERROR_PAGE_LINK");
+        std::string additionalHtml;
+
+        if (additionalErrorLink.has_value())
+        {
+            additionalHtml = format("<a href=\"%S\"> <cite> %S </cite></a> and ", additionalErrorLink->c_str(), additionalErrorLink->c_str());
+        }
+
+        std::string formattedError;
+        if (!specificError.empty())
+        {
+            formattedError = format("<h2>Specific error detected by ANCM:</h2><h3>%s</h3>", specificError.c_str());
+        }
+
+        std::string formattedErrorReason;
+        if (!errorReason.empty())
+        {
+            formattedErrorReason = format("<h2> Common solutions to this issue: </h2>%s", errorReason.c_str());
+        }
+
+        return format(data, statusCode, subStatusCode, specificReasonPhrase.c_str(), statusCode, subStatusCode, specificReasonPhrase.c_str(), formattedErrorReason.c_str(), formattedError.c_str(), additionalHtml.c_str());
+    }
+    catch (...)
+    {
+        OBSERVE_CAUGHT_EXCEPTION();
+        return "";
+    }
+}
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.h
index 686e810cbe..fc3ce8935b 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/file_utility.h
@@ -28,7 +28,11 @@ public:
 
     static
     std::string
-    GetHtml(HMODULE module, int page);
+    GetHtml(HMODULE module, int page, USHORT statusCode, USHORT subStatusCode, const std::string& speicificReasonPhrase, const std::string& solution);
+
+    static
+    std::string
+    GetHtml(HMODULE module, int page, USHORT statusCode, USHORT subStatusCode, const std::string& speicificReasonPhrase, const std::string& solution, const std::string& error);
 
 private:
     static
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/requesthandler.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/requesthandler.h
index 6274efc07e..1c78fcd0ca 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/requesthandler.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/requesthandler.h
@@ -75,7 +75,7 @@ public:
     {
     }
 
-private:
+protected:
     IHttpContext& m_pHttpContext;
     mutable LONG  m_cRefs = 1;
 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
index 04ee2e0944..9535d1c0cb 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
@@ -43,7 +43,7 @@
 #define ASPNETCORE_EVENT_INPROCESS_THREAD_EXCEPTION_MSG      L"Application '%s' with physical root '%s' hit unexpected managed exception, exception code = '0x%x'. Please check the stderr logs for more information."
 #define ASPNETCORE_EVENT_INPROCESS_THREAD_EXCEPTION_STDOUT_MSG L"Application '%s' with physical root '%s' hit unexpected managed exception, exception code = '0x%x'. First 30KB characters of captured stdout and stderr logs:\r\n%s"
 #define ASPNETCORE_EVENT_INPROCESS_RH_ERROR_MSG              L"Could not find 'aspnetcorev2_inprocess.dll'. Exception message:\r\n%s"
-#define ASPNETCORE_EVENT_INPROCESS_RH_REFERENCE_MSG          L"Could not find the assembly '%s' referenced for the in-process application. Please confirm the Microsoft.AspNetCore.Server.IIS package is referenced in your application."
+#define ASPNETCORE_EVENT_INPROCESS_RH_REFERENCE_MSG          L"Could not find the assembly '%s' referenced for the in-process application. Please confirm the Microsoft.AspNetCore.Server.IIS or Microsoft.AspNetCore.App is referenced in your application."
 #define ASPNETCORE_EVENT_OUT_OF_PROCESS_RH_MISSING_MSG       L"Could not find the assembly '%s' for out-of-process application. Please confirm the assembly is installed correctly for IIS or IISExpress."
 #define ASPNETCORE_EVENT_INPROCESS_START_SUCCESS_MSG         L"Application '%s' started successfully."
 #define ASPNETCORE_EVENT_INPROCESS_START_ERROR_MSG           L"Application '%s' failed to start. Exception message:\r\n%s"
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessRhStaticHtml.htm b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessRhStaticHtml.htm
index 59d6b0dacb..8783b58adb 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessRhStaticHtml.htm
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessRhStaticHtml.htm
@@ -2,7 +2,7 @@
 <html lang="en-US" xmlns="http://www.w3.org/1999/xhtml">
     <head>
         <meta charset="utf-8" />
-        <title> HTTP Error 500.30 - ANCM In-Process Start Failure </title>
+        <title> HTTP Error %d.%d - %s </title>
         <style>
             body {
                 font-family: 'Segoe UI', Tahoma, Arial, Helvetica, sans-serif;
@@ -58,14 +58,11 @@
         </style>
     </head>
     <body>
-        <h1> HTTP Error 500.30 - ANCM In-Process Start Failure </h1>
+        <h1> HTTP Error %d.%d - %s </h1>
 
-        <h2> Common causes of this issue: </h2>
-        <ul>
-            <li> The application failed to start </li>
-            <li> The application started but then stopped </li>
-            <li> The application started but threw an exception during startup </li>
-        </ul>
+        %s
+
+        %s
 
         <h2> Troubleshooting steps: </h2>
         <ul>
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/StartupExceptionApplication.h b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/StartupExceptionApplication.h
index 6db5fee164..d3e50e620f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/StartupExceptionApplication.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/StartupExceptionApplication.h
@@ -13,15 +13,18 @@ public:
     StartupExceptionApplication(
         IHttpServer& pServer,
         IHttpApplication& pApplication,
-        HINSTANCE moduleInstance,
         BOOL disableLogs,
         HRESULT hr,
-        std::vector<byte>&& errorPageContent
-        )
+        const std::string& errorPageContent,
+        USHORT statusCode,
+        USHORT subStatusCode,
+        const std::string& statusText)
         : m_disableLogs(disableLogs),
         m_HR(hr),
-        m_moduleInstance(moduleInstance),
-        m_errorPageContent(std::move(errorPageContent)),
+        m_error(errorPageContent),
+        m_statusCode(statusCode),
+        m_subStatusCode(subStatusCode),
+        m_statusText(std::move(statusText)),
         InProcessApplicationBase(pServer, pApplication)
     {
     }
@@ -30,15 +33,17 @@ public:
 
     HRESULT CreateHandler(IHttpContext* pHttpContext, IREQUEST_HANDLER** pRequestHandler)
     {
-        *pRequestHandler = new ServerErrorHandler(*pHttpContext, 500, 30, "Internal Server Error", m_HR, m_moduleInstance, m_disableLogs, IN_PROCESS_RH_STATIC_HTML, m_errorPageContent);
+        *pRequestHandler = new ServerErrorHandler(*pHttpContext, m_statusCode, m_subStatusCode, m_statusText, m_HR, m_disableLogs, m_error);
 
         return S_OK;
     }
 
 private:
-    std::vector<byte> m_errorPageContent;
+    std::string m_error;
     BOOL m_disableLogs;
     HRESULT m_HR;
-    HINSTANCE m_moduleInstance;
+    USHORT m_statusCode;
+    USHORT m_subStatusCode;
+    std::string m_statusText;
 };
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/dllmain.cpp b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/dllmain.cpp
index 710bbee754..cd9261a56c 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/dllmain.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/dllmain.cpp
@@ -17,6 +17,7 @@
 #include "WebConfigConfigurationSource.h"
 #include "ConfigurationLoadException.h"
 #include "StartupExceptionApplication.h"
+#include "file_utility.h"
 
 DECLARE_DEBUG_PRINT_OBJECT("aspnetcorev2_inprocess.dll");
 
@@ -28,7 +29,7 @@ HINSTANCE           g_hWinHttpModule;
 HINSTANCE           g_hAspNetCoreModule;
 HANDLE              g_hEventLog = NULL;
 bool                g_fInProcessApplicationCreated = false;
-std::vector<byte>   g_errorPageContent;
+std::string         g_errorPageContent;
 HINSTANCE           g_hServerModule;
 
 HRESULT
@@ -120,6 +121,10 @@ CreateApplication(
         g_fInProcessApplicationCreated = true;
 
         std::unique_ptr<IN_PROCESS_APPLICATION, IAPPLICATION_DELETER> inProcessApplication;
+
+        // TODO not sure how easy it will be to untangle errors here
+        // ErrorContext errorContext;
+
         if (!FAILED_LOG(hr = IN_PROCESS_APPLICATION::Start(*pServer, pSite, *pHttpApplication, pParameters, nParameters, inProcessApplication)))
         {
             *ppApplication = inProcessApplication.release();
@@ -129,7 +134,20 @@ CreateApplication(
             std::unique_ptr<InProcessOptions> options;
             THROW_IF_FAILED(InProcessOptions::Create(*pServer, pSite, *pHttpApplication, options));
             // Set the currently running application to a fake application that returns startup exceptions.
-            auto pErrorApplication = std::make_unique<StartupExceptionApplication>(*pServer, *pHttpApplication, g_hServerModule, options->QueryDisableStartUpErrorPage(), hr, std::move(g_errorPageContent));
+            auto pErrorApplication = std::make_unique<StartupExceptionApplication>(*pServer,
+                *pHttpApplication,
+                options->QueryDisableStartUpErrorPage(),
+                hr,
+                FILE_UTILITY::GetHtml(g_hServerModule,
+                    IN_PROCESS_RH_STATIC_HTML,
+                    500i16,
+                    30i16,
+                    "ANCM In-Process Start Failure",
+                    "<ul><li>The application failed to start</li><li>The application started but then stopped</li><li>The application started but threw an exception during startup</li></ul>",
+                    g_errorPageContent),
+                500i16,
+                30i16,
+                "Internal Server Error");
 
             RETURN_IF_FAILED(pErrorApplication->StartMonitoringAppOffline());
             *ppApplication = pErrorApplication.release();
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/managedexports.cpp b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/managedexports.cpp
index e52ec8c8e4..a7bcaa3675 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/managedexports.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/managedexports.cpp
@@ -7,7 +7,7 @@
 #include "EventLog.h"
 
 extern bool g_fInProcessApplicationCreated;
-extern std::vector<byte> g_errorPageContent;
+extern std::string g_errorPageContent;
 extern IHttpServer* g_pHttpServer;
 
 //
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/OutOfProcessRhStaticHtml.htm b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/OutOfProcessRhStaticHtml.htm
index e7d2f04e7c..bedf0a8dce 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/OutOfProcessRhStaticHtml.htm
+++ b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/OutOfProcessRhStaticHtml.htm
@@ -2,7 +2,7 @@
 <html lang="en-US" xmlns="http://www.w3.org/1999/xhtml">
     <head>
         <meta charset="utf-8" />
-        <title> HTTP Error 502.5 - ANCM Out-Of-Process Startup Failure </title>
+        <title> HTTP Error %d.%d - %s </title>
         <style>
             body {
                 font-family: 'Segoe UI', Tahoma, Arial, Helvetica, sans-serif;
@@ -58,17 +58,13 @@
         </style>
     </head>
     <body>
-        <h1> HTTP Error 502.5 - ANCM Out-Of-Process Startup Failure </h1>
+        <h1> HTTP Error %d.%d - %s </h1>
 
-        <h1> Common causes of this issue: </h1>
+        %s
 
-        <ul>
-            <li> The application process failed to start </li>
-            <li> The application process started but then stopped </li>
-            <li> The application process started but failed to listen on the configured port </li>
-        </ul>
+        %s
 
-        <h4> Troubleshooting steps: </h4>
+        <h2> Troubleshooting steps: </h2>
 
         <ul>
             <li> Check the system event log for error messages </li>
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/forwardinghandler.cpp b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/forwardinghandler.cpp
index 551d10c9f9..4fbf2abf40 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/forwardinghandler.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/forwardinghandler.cpp
@@ -4,8 +4,10 @@
 #include "forwardinghandler.h"
 #include "url_utility.h"
 #include "exceptions.h"
+#include "ServerErrorApplication.h"
 #include "ServerErrorHandler.h"
 #include "resource.h"
+#include "file_utility.h"
 
 // Just to be aware of the FORWARDING_HANDLER object size.
 C_ASSERT(sizeof(FORWARDING_HANDLER) <= 632);
@@ -302,7 +304,21 @@ Failure:
     }
     else if (fFailedToStartKestrel && !m_pApplication->QueryConfig()->QueryDisableStartUpErrorPage())
     {
-        ServerErrorHandler handler(*m_pW3Context, 502, 5, "Bad Gateway", hr, g_hOutOfProcessRHModule, m_pApplication->QueryConfig()->QueryDisableStartUpErrorPage(), OUT_OF_PROCESS_RH_STATIC_HTML);
+        static std::string htmlResponse = FILE_UTILITY::GetHtml(g_hOutOfProcessRHModule,
+            OUT_OF_PROCESS_RH_STATIC_HTML,
+            502,
+            5,
+            "ANCM Out-Of-Process Startup Failure",
+            "<ul><li> The application process failed to start </li><li> The application process started but then stopped </li><li> The application process started but failed to listen on the configured port </li></ul>");
+
+        ServerErrorHandler handler(*m_pW3Context,
+            502,
+            5,
+            "Bad Gateway",
+            hr,
+            m_pApplication->QueryConfig()->QueryDisableStartUpErrorPage(),
+            htmlResponse);
+
         handler.ExecuteRequestHandler();
     }
     else
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
index 4374ba519a..7acbc1d2e3 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
@@ -7,6 +7,7 @@ using System.Diagnostics;
 using System.IO;
 using System.Linq;
 using System.Net;
+using System.Net.Http;
 using System.Text.RegularExpressions;
 using System.Threading;
 using System.Threading.Tasks;
@@ -268,11 +269,60 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
                 Path.Combine(deploymentResult.ContentRoot, "aspnetcorev2_inprocess.dll"),
                 Path.Combine(deploymentResult.ContentRoot, "hostfxr.dll"),
                 true);
-            await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+
+            if (DeployerSelector.HasNewShim)
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.32 - ANCM Failed to Load dll");
+            }
+            else
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+            }
 
             EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessHostfxrInvalid(deploymentResult), Logger);
         }
 
+        [ConditionalFact]
+        public async Task PublishWithWrongBitness()
+        {
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
+
+            if (deploymentParameters.ServerType == ServerType.IISExpress)
+            {
+                // TODO skip conditions for IISExpress
+                return;
+            }
+
+            deploymentParameters.ApplicationType = ApplicationType.Standalone;
+            deploymentParameters.AddServerConfigAction(element =>
+            {
+                element.RequiredElement("system.applicationHost").RequiredElement("applicationPools").RequiredElement("add").SetAttributeValue("enable32BitAppOnWin64", "true");
+            });
+
+            // Change ANCM dll to 32 bit
+            deploymentParameters.AddServerConfigAction(
+                           element =>
+                           {
+                               var ancmElement = element
+                                   .RequiredElement("system.webServer")
+                                   .RequiredElement("globalModules")
+                                   .Elements("add")
+                                   .FirstOrDefault(e => e.Attribute("name").Value == "AspNetCoreModuleV2");
+
+                               ancmElement.SetAttributeValue("image", ancmElement.Attribute("image").Value.Replace("x64", "x86"));
+                           });
+            var deploymentResult = await DeployAsync(deploymentParameters);
+
+            if (DeployerSelector.HasNewShim)
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "500.32 - ANCM Failed to Load dll");
+            }
+            else
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "500.0 - ANCM In-Process Handler Load Failure");
+            }
+        }
+
         [ConditionalFact]
         [RequiresNewShim]
         public async Task RemoveHostfxrFromApp_InProcessHostfxrLoadFailure()
@@ -283,7 +333,15 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
 
             // We don't distinguish between load failure types so making dll empty should be enough
             File.WriteAllText(Path.Combine(deploymentResult.ContentRoot, "hostfxr.dll"), "");
-            await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+
+            if (DeployerSelector.HasNewShim)
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.32 - ANCM Failed to Load dll");
+            }
+            else
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+            }
 
             EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessHostfxrUnableToLoad(deploymentResult), Logger);
         }
@@ -295,7 +353,14 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             var deploymentResult = await DeployAsync(deploymentParameters);
 
             Helpers.ModifyFrameworkVersionInRuntimeConfig(deploymentResult);
-            await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+            if (DeployerSelector.HasNewShim)
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.31 - ANCM Failed to Find Native Dependencies");
+            }
+            else
+            {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+            }
 
             EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessFailedToFindNativeDependencies(deploymentResult), Logger);
         }
@@ -309,14 +374,23 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
 
             File.Delete(Path.Combine(deploymentResult.ContentRoot, "aspnetcorev2_inprocess.dll"));
 
-            await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
-
-            if (DeployerSelector.IsForwardsCompatibilityTest)
+            if (DeployerSelector.HasNewShim && DeployerSelector.HasNewHandler)
             {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.33 - ANCM Request Handler Load Failure ");
+
+                EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessFailedToFindRequestHandler(deploymentResult), Logger);
+            }
+            else if (DeployerSelector.HasNewShim)
+            {
+                // Forwards compat tests fail earlier due to a error with the M.AspNetCore.Server.IIS package.
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.31 - ANCM Failed to Find Native Dependencies");
+
                 EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessFailedToFindNativeDependencies(deploymentResult), Logger);
             }
             else
             {
+                await AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult);
+
                 EventLogHelpers.VerifyEventLogEvent(deploymentResult, EventLogHelpers.InProcessFailedToFindRequestHandler(deploymentResult), Logger);
             }
         }
@@ -750,11 +824,23 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             });
         }
 
-        private async Task AssertSiteFailsToStartWithInProcessStaticContent(IISDeploymentResult deploymentResult)
+        private Task AssertSiteFailsToStartWithInProcessStaticContent(IISDeploymentResult deploymentResult)
         {
-            var response = await deploymentResult.HttpClient.GetAsync("/HelloWorld");
+            return AssertSiteFailsToStartWithInProcessStaticContent(deploymentResult, "HTTP Error 500.0 - ANCM In-Process Handler Load Failure");
+        }
+
+        private async Task AssertSiteFailsToStartWithInProcessStaticContent(IISDeploymentResult deploymentResult, string error)
+        {
+            HttpResponseMessage response = null;
+
+            // Make sure strings aren't freed.
+            for (var i = 0; i < 2; i++)
+            {
+                response = await deploymentResult.HttpClient.GetAsync("/HelloWorld");
+            }
+
             Assert.Equal(HttpStatusCode.InternalServerError, response.StatusCode);
-            Assert.Contains("HTTP Error 500.0 - ANCM In-Process Handler Load Failure", await response.Content.ReadAsStringAsync());
+            Assert.Contains(error, await response.Content.ReadAsStringAsync());
             StopServer();
         }
     }
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
index 87d9c73dd0..d22856610f 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
@@ -47,6 +47,12 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             Assert.Equal(200, (int)result1.StatusCode);
             Assert.Equal(500, (int)result2.StatusCode);
             StopServer();
+
+            if (DeployerSelector.HasNewShim)
+            {
+                Assert.Contains("500.35 - ANCM Multiple In-Process Applications in same Process", await result2.Content.ReadAsStringAsync());
+            }
+
             EventLogHelpers.VerifyEventLogEvent(result, EventLogHelpers.OnlyOneAppPerAppPool(), Logger);
         }
 
@@ -68,6 +74,12 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             Assert.Equal(200, (int)result1.StatusCode);
             Assert.Equal(500, (int)result2.StatusCode);
             StopServer();
+
+            if (DeployerSelector.HasNewShim)
+            {
+                Assert.Contains("500.34 - ANCM Mixed Hosting Models Not Supported", await result2.Content.ReadAsStringAsync());
+            }
+
             EventLogHelpers.VerifyEventLogEvent(result, "Mixed hosting model is not supported.", Logger);
         }
 
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Utilities/EventLogHelpers.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Utilities/EventLogHelpers.cs
index d2a94632c4..a487ba20dd 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Utilities/EventLogHelpers.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Utilities/EventLogHelpers.cs
@@ -259,7 +259,15 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
 
         public static string InProcessFailedToFindRequestHandler(IISDeploymentResult deploymentResult)
         {
-            return "Could not find the assembly '(.*)' referenced for the in-process application. Please confirm the Microsoft.AspNetCore.Server.IIS package is referenced in your application.";
+            if (DeployerSelector.HasNewShim)
+            {
+                return "Could not find the assembly '(.*)' referenced for the in-process application. Please confirm the Microsoft.AspNetCore.Server.IIS or Microsoft.AspNetCore.App is referenced in your application.";
+
+            }
+            else
+            {
+                return "Could not find the assembly '(.*)' referenced for the in-process application. Please confirm the Microsoft.AspNetCore.Server.IIS package is referenced in your application.";
+            }
         }
 
         public static string CouldNotStartStdoutFileRedirection(string file, IISDeploymentResult deploymentResult)
diff --git a/src/Servers/IIS/IntegrationTesting.IIS/src/IISDeploymentParameters.cs b/src/Servers/IIS/IntegrationTesting.IIS/src/IISDeploymentParameters.cs
index 04d4dfa7ce..b57a68eff1 100644
--- a/src/Servers/IIS/IntegrationTesting.IIS/src/IISDeploymentParameters.cs
+++ b/src/Servers/IIS/IntegrationTesting.IIS/src/IISDeploymentParameters.cs
@@ -47,6 +47,5 @@ namespace Microsoft.AspNetCore.Server.IntegrationTesting.IIS
         public IDictionary<string, string> WebConfigBasedEnvironmentVariables { get; set; } = new Dictionary<string, string>();
 
         public IDictionary<string, string> HandlerSettings { get; set; } = new Dictionary<string, string>();
-
     }
 }