diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AppOfflineHandler.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AppOfflineHandler.h
index 33afc803bc87..e7da69eff2f6 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AppOfflineHandler.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/AppOfflineHandler.h
@@ -11,8 +11,8 @@ class AppOfflineHandler: public REQUEST_HANDLER
 public:
     AppOfflineHandler(IHttpContext& pContext, const std::string& appOfflineContent)
         : REQUEST_HANDLER(pContext),
-          m_pContext(pContext),
-          m_strAppOfflineContent(appOfflineContent)
+        m_pContext(pContext),
+        m_strAppOfflineContent(appOfflineContent)
     {
     }
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ApplicationFactory.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ApplicationFactory.h
index 23c5a67d409f..9906251f532f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ApplicationFactory.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ApplicationFactory.h
@@ -32,15 +32,17 @@ class ApplicationFactory
     HRESULT Execute(
         _In_  IHttpServer           *pServer,
         _In_  IHttpContext          *pHttpContext,
+        _In_  std::wstring&   shadowCopyDirectory,
         _Outptr_ IAPPLICATION       **pApplication) const
     {
         // m_location.data() is const ptr copy to local to get mutable pointer
         auto location = m_location;
-        std::array<APPLICATION_PARAMETER, 3> parameters {
+        std::array<APPLICATION_PARAMETER, 4> parameters {
             {
                 {"InProcessExeLocation", location.data()},
                 {"TraceContext", pHttpContext->GetTraceContext()},
-                {"Site", pHttpContext->GetSite()}
+                {"Site", pHttpContext->GetSite()},
+                {"ShadowCopyDirectory", shadowCopyDirectory.data()}
             }
         };
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
index 2a1303bcdf2f..03096d658699 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.cpp
@@ -29,6 +29,7 @@ HandlerResolver::HandlerResolver(HMODULE hModule, const IHttpServer &pServer)
 
 HRESULT
 HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication,
+    const std::filesystem::path& shadowCopyPath,
     const ShimOptions& pConfiguration,
     std::unique_ptr<ApplicationFactory>& pApplicationFactory,
     ErrorContext& errorContext)
@@ -62,7 +63,7 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
             RETURN_IF_FAILED(HostFxrResolutionResult::Create(
                 L"",
                 pConfiguration.QueryProcessPath(),
-                pApplication.GetApplicationPhysicalPath(),
+                shadowCopyPath.empty() ? pApplication.GetApplicationPhysicalPath() : shadowCopyPath,
                 pConfiguration.QueryArguments(),
                 errorContext,
                 options));
@@ -125,7 +126,7 @@ HandlerResolver::LoadRequestHandlerAssembly(const IHttpApplication &pApplication
 }
 
 HRESULT
-HandlerResolver::GetApplicationFactory(const IHttpApplication& pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext)
+HandlerResolver::GetApplicationFactory(const IHttpApplication& pApplication, const std::filesystem::path& shadowCopyPath, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext)
 {
     SRWExclusiveLock lock(m_requestHandlerLoadLock);
     if (m_loadedApplicationHostingModel != HOSTING_UNKNOWN)
@@ -168,7 +169,7 @@ HandlerResolver::GetApplicationFactory(const IHttpApplication& pApplication, std
 
     m_loadedApplicationHostingModel = options.QueryHostingModel();
     m_loadedApplicationId = pApplication.GetApplicationId();
-    RETURN_IF_FAILED(LoadRequestHandlerAssembly(pApplication, options, pApplicationFactory, errorContext));
+    RETURN_IF_FAILED(LoadRequestHandlerAssembly(pApplication, shadowCopyPath, options, pApplicationFactory, errorContext));
 
     return S_OK;
 }
@@ -181,6 +182,13 @@ void HandlerResolver::ResetHostingModel()
     m_loadedApplicationId.resize(0);
 }
 
+APP_HOSTING_MODEL HandlerResolver::GetHostingModel()
+{
+    SRWExclusiveLock lock(m_requestHandlerLoadLock);
+
+    return m_loadedApplicationHostingModel;
+}
+
 HRESULT
 HandlerResolver::FindNativeAssemblyFromGlobalLocation(
     const ShimOptions& pConfiguration,
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
index 59e1b01ac63b..4ca4d231d950 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/HandlerResolver.h
@@ -15,11 +15,12 @@ class HandlerResolver
 {
 public:
     HandlerResolver(HMODULE hModule, const IHttpServer &pServer);
-    HRESULT GetApplicationFactory(const IHttpApplication &pApplication, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext);
+    HRESULT GetApplicationFactory(const IHttpApplication &pApplication, const std::filesystem::path& shadowCopyPath, std::unique_ptr<ApplicationFactory>& pApplicationFactory, const ShimOptions& options, ErrorContext& errorContext);
     void ResetHostingModel();
+    APP_HOSTING_MODEL GetHostingModel();
 
 private:
-    HRESULT LoadRequestHandlerAssembly(const IHttpApplication &pApplication, const ShimOptions& pConfiguration, std::unique_ptr<ApplicationFactory>& pApplicationFactory, ErrorContext& errorContext);
+    HRESULT LoadRequestHandlerAssembly(const IHttpApplication &pApplication, const std::filesystem::path& shadowCopyPath, 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,
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
index 353b0be78866..c43b2c62a0c2 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.cpp
@@ -8,6 +8,9 @@
 #include "Environment.h"
 
 #define CS_ASPNETCORE_HANDLER_VERSION                    L"handlerVersion"
+#define CS_ASPNETCORE_SHADOW_COPY                        L"experimentalEnableShadowCopy"
+#define CS_ASPNETCORE_SHADOW_COPY_DIRECTORY              L"shadowCopyDirectory"
+#define CS_ASPNETCORE_CLEAN_SHADOW_DIRECTORY_CONTENT     L"cleanShadowCopyDirectory"
 
 ShimOptions::ShimOptions(const ConfigurationSource &configurationSource) :
         m_hostingModel(HOSTING_UNKNOWN),
@@ -31,12 +34,22 @@ ShimOptions::ShimOptions(const ConfigurationSource &configurationSource) :
             "or hostingModel=\"outofprocess\" in the web.config file.", hostingModel.c_str()));
     }
 
+    const auto handlerSettings = section->GetKeyValuePairs(CS_ASPNETCORE_HANDLER_SETTINGS);
+
     if (m_hostingModel == HOSTING_OUT_PROCESS)
     {
-        const auto handlerSettings = section->GetKeyValuePairs(CS_ASPNETCORE_HANDLER_SETTINGS);
         m_strHandlerVersion = find_element(handlerSettings, CS_ASPNETCORE_HANDLER_VERSION).value_or(std::wstring());
     }
 
+    auto experimentalEnableShadowCopyElement = find_element(handlerSettings, CS_ASPNETCORE_SHADOW_COPY).value_or(std::wstring());
+    m_fexperimentalEnableShadowCopying = equals_ignore_case(L"true", experimentalEnableShadowCopyElement);
+
+    auto cleanShadowCopyDirectory = find_element(handlerSettings, CS_ASPNETCORE_CLEAN_SHADOW_DIRECTORY_CONTENT).value_or(std::wstring());
+    m_fCleanShadowCopyDirectory = equals_ignore_case(L"true", cleanShadowCopyDirectory);
+
+    m_strShadowCopyingDirectory = find_element(handlerSettings, CS_ASPNETCORE_SHADOW_COPY_DIRECTORY)
+        .value_or(m_fexperimentalEnableShadowCopying ? L"ShadowCopyDirectory" : std::wstring());
+
     m_strProcessPath = section->GetRequiredString(CS_ASPNETCORE_PROCESS_EXE_PATH);
     m_strArguments = section->GetString(CS_ASPNETCORE_PROCESS_ARGUMENTS).value_or(CS_ASPNETCORE_PROCESS_ARGUMENTS_DEFAULT);
     m_fStdoutLogEnabled = section->GetRequiredBool(CS_ASPNETCORE_STDOUT_LOG_ENABLED);
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
index 5d1c04f8ab07..9674e9a0244f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/ShimOptions.h
@@ -65,6 +65,24 @@ class ShimOptions: NonCopyable
         return m_fShowDetailedErrors;
     }
 
+    bool
+    QueryShadowCopyEnabled() const noexcept
+    {
+        return m_fexperimentalEnableShadowCopying;
+    }
+
+    bool
+    QueryCleanShadowCopyDirectory() const noexcept
+    {
+        return m_fCleanShadowCopyDirectory;
+    }
+
+    const std::wstring&
+    QueryShadowCopyDirectory() const noexcept
+    {
+        return m_strShadowCopyingDirectory;
+    }
+
     ShimOptions(const ConfigurationSource &configurationSource);
 
 private:
@@ -76,4 +94,7 @@ class ShimOptions: NonCopyable
     bool                           m_fStdoutLogEnabled;
     bool                           m_fDisableStartupPage;
     bool                           m_fShowDetailedErrors;
+    bool                           m_fexperimentalEnableShadowCopying;
+    bool                           m_fCleanShadowCopyDirectory;
+    std::wstring                   m_strShadowCopyingDirectory;
 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
index 994061cadcfb..043e59f08743 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.cpp
@@ -18,6 +18,7 @@
 #include "file_utility.h"
 
 extern HINSTANCE           g_hServerModule;
+extern BOOL                g_fInAppOfflineShutdown;
 
 HRESULT
 APPLICATION_INFO::CreateHandler(
@@ -49,7 +50,6 @@ APPLICATION_INFO::CreateHandler(
         while (hr != S_OK)
         {
             // At this point application is either null or shutdown and is returning S_FALSE
-
             if (m_pApplication != nullptr)
             {
                 LOG_INFO(L"Application went offline");
@@ -80,11 +80,25 @@ APPLICATION_INFO::CreateApplication(IHttpContext& pHttpContext)
 
         return S_OK;
     }
+
     try
     {
         const WebConfigConfigurationSource configurationSource(m_pServer.GetAdminManager(), pHttpApplication);
         ShimOptions options(configurationSource);
 
+        if (g_fInAppOfflineShutdown)
+        {
+            m_pApplication = make_application<ServerErrorApplication>(
+                pHttpApplication,
+                E_FAIL,
+                options.QueryDisableStartupPage() /* disableStartupPage */,
+                "" /* responseContent */,
+                503i16 /* statusCode */,
+                0i16 /* subStatusCode */,
+                "Application Shutting Down");
+            return S_OK;
+        }
+
         ErrorContext errorContext;
         errorContext.statusCode = 500i16;
         errorContext.subStatusCode = 0i16;
@@ -130,6 +144,7 @@ APPLICATION_INFO::CreateApplication(IHttpContext& pHttpContext)
     }
     catch (...)
     {
+        OBSERVE_CAUGHT_EXCEPTION();
         EventLog::Error(
             ASPNETCORE_CONFIGURATION_LOAD_ERROR,
             ASPNETCORE_CONFIGURATION_LOAD_ERROR_MSG,
@@ -175,13 +190,17 @@ APPLICATION_INFO::TryCreateApplication(IHttpContext& pHttpContext, const ShimOpt
         }
     }
 
-    RETURN_IF_FAILED(m_handlerResolver.GetApplicationFactory(*pHttpContext.GetApplication(), m_pApplicationFactory, options, error));
+    auto shadowCopyPath = HandleShadowCopy(options, pHttpContext);
+
+    RETURN_IF_FAILED(m_handlerResolver.GetApplicationFactory(*pHttpContext.GetApplication(), shadowCopyPath, m_pApplicationFactory, options, error));
     LOG_INFO(L"Creating handler application");
 
     IAPPLICATION * newApplication;
+    std::wstring shadowCopyWstring = shadowCopyPath.wstring();
     RETURN_IF_FAILED(m_pApplicationFactory->Execute(
         &m_pServer,
         &pHttpContext,
+        shadowCopyWstring,
         &newApplication));
 
     m_pApplication.reset(newApplication);
@@ -206,19 +225,91 @@ APPLICATION_INFO::TryCreateHandler(
             return S_OK;
         }
     }
+
     return S_FALSE;
 }
 
 VOID
 APPLICATION_INFO::ShutDownApplication(const bool fServerInitiated)
 {
+    IAPPLICATION* app = nullptr;
+    {
+        SRWExclusiveLock lock(m_applicationLock);
+        if (!m_pApplication)
+        {
+            return;
+        }
+        app = m_pApplication.get();
+    }
+
+    LOG_INFOF(L"Stopping application '%ls'", QueryApplicationInfoKey().c_str());
+    app->Stop(fServerInitiated);
+
     SRWExclusiveLock lock(m_applicationLock);
 
-    if (m_pApplication)
+    m_pApplication = nullptr;
+    m_pApplicationFactory = nullptr;
+}
+
+std::filesystem::path
+APPLICATION_INFO::HandleShadowCopy(const ShimOptions& options, IHttpContext& pHttpContext)
+{
+    std::filesystem::path shadowCopyPath;
+
+    // Only support shadow copying for IIS.
+    if (options.QueryShadowCopyEnabled() && !m_pServer.IsCommandLineLaunch())
     {
-        LOG_INFOF(L"Stopping application '%ls'", QueryApplicationInfoKey().c_str());
-        m_pApplication->Stop(fServerInitiated);
-        m_pApplication = nullptr;
-        m_pApplicationFactory = nullptr;
+        shadowCopyPath = options.QueryShadowCopyDirectory();
+        std::wstring physicalPath = pHttpContext.GetApplication()->GetApplicationPhysicalPath();
+
+        // Make shadow copy path absolute.
+        if (!shadowCopyPath.is_absolute())
+        {
+            shadowCopyPath = std::filesystem::absolute(std::filesystem::path(physicalPath) / shadowCopyPath);
+        }
+
+        // The shadow copy directory itself isn't copied to directly.
+        // Instead subdirectories with numerically increasing names are created.
+        // This is because on shutdown, the app itself will still have all dlls loaded,
+        // meaning we can't copy to the same subdirectory. Therefore, on shutdown,
+        // we create a directory that is one larger than the previous largest directory number.
+        auto directoryName = 0;
+        std::string directoryNameStr = "0";
+        auto shadowCopyBaseDirectory = std::filesystem::directory_entry(shadowCopyPath);
+        if (!shadowCopyBaseDirectory.exists())
+        {
+            CreateDirectory(shadowCopyBaseDirectory.path().wstring().c_str(), NULL);
+        }
+
+        for (auto& entry : std::filesystem::directory_iterator(shadowCopyPath))
+        {
+            if (entry.is_directory())
+            {
+                try
+                {
+                    auto tempDirName = entry.path().filename().string();
+                    int intFileName = std::stoi(tempDirName);
+                    if (intFileName > directoryName)
+                    {
+                        directoryName = intFileName;
+                        directoryNameStr = tempDirName;
+                    }
+                }
+                catch (...)
+                {
+                    OBSERVE_CAUGHT_EXCEPTION();
+                    // Ignore any folders that can't be converted to an int.
+                }
+            }
+        }
+
+        shadowCopyPath = shadowCopyPath / directoryNameStr;
+        HRESULT hr = Environment::CopyToDirectory(physicalPath, shadowCopyPath, options.QueryCleanShadowCopyDirectory(), std::filesystem::canonical(shadowCopyBaseDirectory.path()));
+        if (hr != S_OK)
+        {
+            return std::wstring();
+        }
     }
+
+    return shadowCopyPath;
 }
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
index e16eae191337..a54107eb8bee 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationinfo.h
@@ -79,6 +79,9 @@ class APPLICATION_INFO: NonCopyable
     HRESULT
     TryCreateApplication(IHttpContext& pHttpContext, const ShimOptions& options, ErrorContext& error);
 
+    std::filesystem::path
+    HandleShadowCopy(const ShimOptions& options, IHttpContext& pHttpContext);
+
     IHttpServer            &m_pServer;
     HandlerResolver        &m_handlerResolver;
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationmanager.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationmanager.cpp
index d940b39302b7..7bc3bd2599dd 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationmanager.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/applicationmanager.cpp
@@ -10,6 +10,7 @@
 #include "EventLog.h"
 
 extern BOOL         g_fInShutdown;
+extern BOOL         g_fInAppOfflineShutdown;
 
 //
 // Retrieves the application info from the application manager
@@ -108,14 +109,33 @@ APPLICATION_MANAGER::RecycleApplicationFromManager(
                 if (itr->second->ConfigurationPathApplies(configurationPath))
                 {
                     applicationsToRecycle.emplace_back(itr->second);
-                    itr = m_pApplicationInfoHash.erase(itr);
+                    // Delay deleting an in-process app until after shutting the application down to avoid creating
+                    // another application info, which would just return app_offline.
+                    if (m_handlerResolver.GetHostingModel() == APP_HOSTING_MODEL::HOSTING_IN_PROCESS)
+                    {
+                        ++itr;
+                    }
+                    else
+                    {
+                        itr = m_pApplicationInfoHash.erase(itr);
+                    }
                 }
                 else
                 {
                     ++itr;
+
                 }
             }
 
+            if (m_handlerResolver.GetHostingModel() == APP_HOSTING_MODEL::HOSTING_IN_PROCESS)
+            {
+                // For detecting app_offline when the app_offline file isn't present.
+                // Normally, app_offline state is independent of application
+                // (Just checks for app_offline file).
+                // For shadow copying, we need some other indication that the app is offline.
+                g_fInAppOfflineShutdown = true;
+            }
+
             // All applications were unloaded reset handler resolver validation logic
             if (m_pApplicationInfoHash.empty())
             {
@@ -155,6 +175,26 @@ APPLICATION_MANAGER::RecycleApplicationFromManager(
                 }
             }
         }
+        {
+            SRWExclusiveLock lock(m_srwLock);
+            const std::wstring configurationPath = pszApplicationId;
+
+            // Remove apps after calling shutdown on each of them
+            // This is exclusive to in-process, as the shutdown of an inprocess app recycles
+            // the entire worker process.
+            auto itr = m_pApplicationInfoHash.begin();
+            while (itr != m_pApplicationInfoHash.end())
+            {
+                if (itr->second != nullptr && itr->second->ConfigurationPathApplies(configurationPath))
+                {
+                    itr = m_pApplicationInfoHash.erase(itr);
+                }
+                else
+                {
+                    ++itr;
+                }
+            }
+        }
     }
     CATCH_RETURN()
 
@@ -172,6 +212,7 @@ APPLICATION_MANAGER::ShutDown()
     // However, it is possible to receive multiple OnGlobalStopListening events
     // Protect against this by checking if we already shut down.
     g_fInShutdown = TRUE;
+    g_fInAppOfflineShutdown = true;
 
     // During shutdown we lock until we delete the application
     SRWExclusiveLock lock(m_srwLock);
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/dllmain.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/dllmain.cpp
index b3a98f0c7e3e..acf90e07c622 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/dllmain.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/dllmain.cpp
@@ -17,6 +17,7 @@ DECLARE_DEBUG_PRINT_OBJECT("aspnetcorev2.dll");
 HANDLE              g_hEventLog = nullptr;
 BOOL                g_fRecycleProcessCalled = FALSE;
 BOOL                g_fInShutdown = FALSE;
+BOOL                g_fInAppOfflineShutdown = FALSE;
 HINSTANCE           g_hServerModule;
 
 VOID
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/proxymodule.cpp b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/proxymodule.cpp
index e3a435bc9b87..162c0fea907b 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/proxymodule.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/AspNetCore/proxymodule.cpp
@@ -100,7 +100,12 @@ ASPNET_CORE_PROXY_MODULE::OnExecuteRequestHandler(
             *pHttpContext,
             m_pApplicationInfo));
 
-        FINISHED_IF_FAILED(m_pApplicationInfo->CreateHandler(*pHttpContext, m_pHandler));
+        FINISHED_IF_FAILED(hr = m_pApplicationInfo->CreateHandler(*pHttpContext, m_pHandler));
+
+        if (m_pHandler == nullptr)
+        {
+            FINISHED(HRESULT_FROM_WIN32(ERROR_SERVER_SHUTDOWN_IN_PROGRESS));
+        }
 
         SetupDisconnectHandler(pHttpContext);
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
index fb63cdb20c99..95fa1bce3c61 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
@@ -151,3 +151,89 @@ bool Environment::IsRunning64BitProcess()
     GetNativeSystemInfo(&systemInfo);
     return systemInfo.wProcessorArchitecture == PROCESSOR_ARCHITECTURE_AMD64;
 }
+
+HRESULT Environment::CopyToDirectory(const std::wstring& source, const std::filesystem::path& destination, bool cleanDest, const std::filesystem::path& directoryToIgnore)
+{
+    if (cleanDest && std::filesystem::exists(destination))
+    {
+        std::filesystem::remove_all(destination);
+    }
+
+    Environment::CopyToDirectoryInner(source, destination, directoryToIgnore);
+    return S_OK;
+}
+
+void Environment::CopyToDirectoryInner(const std::filesystem::path& source, const std::filesystem::path& destination, const std::filesystem::path& directoryToIgnore)
+{
+    auto destinationDirEntry = std::filesystem::directory_entry(destination);
+    if (!destinationDirEntry.exists())
+    {
+        CreateDirectory(destination.wstring().c_str(), NULL);
+    }
+
+    for (auto& path : std::filesystem::directory_iterator(source))
+    {
+        if (path.is_regular_file())
+        {
+            auto sourceFile = path.path().filename();
+            auto destinationPath = (destination / sourceFile);
+
+            if (std::filesystem::directory_entry(destinationPath).exists())
+            {
+                auto sourceFileTime = std::filesystem::last_write_time(path);
+                auto destinationFileTime = std::filesystem::last_write_time(destinationPath);
+                if (sourceFileTime <= destinationFileTime) // file write time is the same
+                {
+                    continue;
+                }
+            }
+
+            CopyFile(path.path().wstring().c_str(), destinationPath.wstring().c_str(), FALSE);
+        }
+        else if (path.is_directory())
+        {
+            auto sourceInnerDirectory = path.path();
+
+            // Make sure we aren't navigating into shadow copy directory.
+            if (sourceInnerDirectory.wstring().rfind(directoryToIgnore, 0) != 0)
+            {
+                CopyToDirectoryInner(path.path(), destination / path.path().filename(), directoryToIgnore);
+            }
+        }
+    }
+}
+
+bool Environment::CheckUpToDate(const std::wstring& source, const std::filesystem::path& destination, const std::wstring& extension, const std::filesystem::path& directoryToIgnore)
+{
+    for (auto& path : std::filesystem::directory_iterator(source))
+    {
+        if (path.is_regular_file()
+            && path.path().has_extension()
+            && path.path().filename().extension().wstring() == extension)
+        {
+            auto sourceFile = path.path().filename();
+            auto destinationPath = (destination / sourceFile);
+
+            if (std::filesystem::directory_entry(destinationPath).exists())
+            {
+                auto originalFileTime = std::filesystem::last_write_time(path);
+                auto destFileTime = std::filesystem::last_write_time(destinationPath);
+                if (originalFileTime > destFileTime) // file write time is the same
+                {
+                    return false;
+                }
+            }
+
+            CopyFile(path.path().wstring().c_str(), destinationPath.wstring().c_str(), FALSE);
+        }
+        else if (path.is_directory())
+        {
+            auto sourceInnerDirectory = std::filesystem::directory_entry(path);
+            if (sourceInnerDirectory.path() != directoryToIgnore)
+            {
+                CheckUpToDate(destination / path.path().filename(), path.path(), extension, directoryToIgnore);
+            }
+        }
+    }
+    return true;
+}
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.h
index 4f2611ef71f2..a0a4d4013c42 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.h
@@ -22,5 +22,12 @@ class Environment
     std::wstring GetDllDirectoryValue();
     static
     bool IsRunning64BitProcess();
+    static
+    HRESULT CopyToDirectory(const std::wstring& source, const std::filesystem::path& destination, bool cleanDest, const std::filesystem::path& directoryToIgnore);
+    static
+    bool CheckUpToDate(const std::wstring& source, const std::filesystem::path& destination, const std::wstring& extension, const std::filesystem::path& directoryToIgnore);
+private:
+    static
+    void CopyToDirectoryInner(const std::filesystem::path& source_folder, const std::filesystem::path& target_folder, const std::filesystem::path& directoryToIgnore);
 };
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
index a6cf2bb889ac..5bb696da311c 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/HostFxr.h
@@ -17,6 +17,7 @@ struct hostfxr_initialize_parameters
 #define DOTNETCORE_STARTUP_HOOK  L"STARTUP_HOOKS"
 #define DOTNETCORE_USE_ENTRYPOINT_FILTER L"USE_ENTRYPOINT_FILTER"
 #define DOTNETCORE_STACK_SIZE L"DEFAULT_STACK_SIZE"
+#define APP_CONTEXT_BASE_DIRECTORY L"APP_CONTEXT_BASE_DIRECTORY"
 #define ASPNETCORE_STARTUP_ASSEMBLY L"Microsoft.AspNetCore.Server.IIS"
 
 typedef INT(*hostfxr_get_native_search_directories_fn) (INT argc, CONST PCWSTR* argv, PWSTR buffer, DWORD buffer_size, DWORD* required_buffer_size);
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp
index cf2395e7b585..9353e427cf77 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/PollingAppOfflineApplication.cpp
@@ -11,6 +11,7 @@
 HRESULT PollingAppOfflineApplication::TryCreateHandler(_In_ IHttpContext* pHttpContext, _Outptr_result_maybenull_ IREQUEST_HANDLER** pRequestHandler)
 {
     CheckAppOffline();
+
     return LOG_IF_FAILED(APPLICATION::TryCreateHandler(pHttpContext, pRequestHandler));
 }
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/application.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/application.h
index ae30844330cc..742ee81a97fd 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/application.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/application.h
@@ -129,11 +129,11 @@ class APPLICATION : public IAPPLICATION
     SRWLOCK m_stopLock{};
     SRWLOCK m_dataLock {};
     bool m_fStopCalled;
+    std::wstring m_applicationPhysicalPath;
 
 private:
     mutable LONG           m_cRefs;
 
-    std::wstring m_applicationPhysicalPath;
     std::wstring m_applicationVirtualPath;
     std::wstring m_applicationConfigPath;
     std::wstring m_applicationId;
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/aspnetcore_msg.mc b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/aspnetcore_msg.mc
index 20d04bd56bf6..ace6bb1b98be 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/aspnetcore_msg.mc
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/aspnetcore_msg.mc
@@ -207,6 +207,12 @@ Language=English
 %1
 .
 
+Messageid=1037
+SymbolicName=ASPNETCORE_EVENT_RECYCLE_FILECHANGE
+Language=English
+%1
+.
+
 
 ;
 ;#endif     // _ASPNETCORE_MODULE_MSG_H_
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
index 9535d1c0cbd8..a561fa50c458 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/resources.h
@@ -33,6 +33,7 @@
 #define ASPNETCORE_EVENT_INPROCESS_THREAD_EXIT_STDOUT_MSG    L"Application '%s' with physical root '%s' has exited from Program.Main with exit code = '%d'. First 30KB characters of captured stdout and stderr logs:\r\n%s"
 #define ASPNETCORE_EVENT_INPROCESS_THREAD_EXIT_MSG           L"Application '%s' with physical root '%s' has exited from Program.Main with exit code = '%d'. Please check the stderr logs for more information."
 #define ASPNETCORE_EVENT_RECYCLE_APPOFFLINE_MSG              L"Application '%s' was recycled after detecting app_offline.htm."
+#define ASPNETCORE_EVENT_RECYCLE_FILECHANGE_MSG              L"Application '%s' was recycled after detecting file change in application directory."
 #define ASPNETCORE_EVENT_MONITOR_APPOFFLINE_ERROR_MSG        L"Failed to monitor app_offline.htm for application '%s', ErrorCode '0x%x'. "
 #define ASPNETCORE_EVENT_RECYCLE_CONFIGURATION_MSG           L"Application '%s' was recycled due to configuration change"
 #define ASPNETCORE_EVENT_RECYCLE_FAILURE_CONFIGURATION_MSG   L"Failed to recycle application after a configuration change at '%s'. Recycling worker process."
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/sttimer.h b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/sttimer.h
index 26d79d073781..86b62b6fcf2a 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/sttimer.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/sttimer.h
@@ -118,13 +118,11 @@ class STTIMER
     VOID
     CALLBACK
     TimerCallback(
-        _In_ PTP_CALLBACK_INSTANCE Instance,
+        _In_ PTP_CALLBACK_INSTANCE ,
         _In_ PVOID Context,
-        _In_ PTP_TIMER Timer
+        _In_ PTP_TIMER 
     )
     {
-        Instance;
-        Timer;
         STRU*                   pstruLogFilePath = (STRU*)Context;
         HANDLE                  hStdoutHandle = NULL;
         SECURITY_ATTRIBUTES     saAttr = { 0 };
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessApplicationBase.cpp b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessApplicationBase.cpp
index fb9fe8a01502..b876d6dc2656 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessApplicationBase.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/InProcessApplicationBase.cpp
@@ -29,6 +29,7 @@ InProcessApplicationBase::StopInternal(bool fServerInitiated)
         // We don't actually handle any shutdown logic here.
         // Instead, we notify IIS that the process needs to be recycled, which will call
         // ApplicationManager->Shutdown(). This will call shutdown on the application.
+        LOG_INFO(L"AspNetCore InProcess Recycle Process on Demand");
         m_pHttpServer.RecycleProcess(L"AspNetCore InProcess Recycle Process on Demand");
     }
     else
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.cpp b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.cpp
index 8643f8089aae..c94236af42e6 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.cpp
@@ -14,7 +14,7 @@
 #include "Environment.h"
 #include "HostFxr.h"
 
-IN_PROCESS_APPLICATION*  IN_PROCESS_APPLICATION::s_Application = NULL;
+IN_PROCESS_APPLICATION* IN_PROCESS_APPLICATION::s_Application = NULL;
 
 IN_PROCESS_APPLICATION::IN_PROCESS_APPLICATION(
     IHttpServer& pHttpServer,
@@ -22,7 +22,8 @@ IN_PROCESS_APPLICATION::IN_PROCESS_APPLICATION(
     std::unique_ptr<InProcessOptions> pConfig,
     APPLICATION_PARAMETER* pParameters,
     DWORD                  nParameters) :
-    InProcessApplicationBase(pHttpServer, pApplication),
+    InProcessApplicationBase(pHttpServer,
+        pApplication),
     m_Initialized(false),
     m_blockManagedCallbacks(true),
     m_waitForShutdown(true),
@@ -37,6 +38,14 @@ IN_PROCESS_APPLICATION::IN_PROCESS_APPLICATION(
         m_dotnetExeKnownLocation = knownLocation;
     }
 
+    const auto shadowCopyDirectory = FindParameter<PCWSTR>(s_shadowCopyDirectoryName, pParameters, nParameters);
+    if (shadowCopyDirectory != nullptr)
+    {
+        m_shadowCopyDirectory = shadowCopyDirectory;
+    }
+
+    m_shutdownTimeout = m_pConfig.get()->QueryShutdownTimeLimitInMS();
+
     m_stringRedirectionOutput = std::make_shared<StringStreamRedirectionOutput>();
 }
 
@@ -48,6 +57,9 @@ IN_PROCESS_APPLICATION::~IN_PROCESS_APPLICATION()
 VOID
 IN_PROCESS_APPLICATION::StopInternal(bool fServerInitiated)
 {
+    // Stop app offline tracking before shutting down CLR.
+    // This is to help with shadow copy scenario where the app is shutting down.
+    AppOfflineTrackingApplication::StopInternal(fServerInitiated);
     StopClr();
     InProcessApplicationBase::StopInternal(fServerInitiated);
 }
@@ -58,7 +70,19 @@ IN_PROCESS_APPLICATION::StopClr()
     // This has the state lock around it.
     LOG_INFO(L"Stopping CLR");
 
-    if (!m_blockManagedCallbacks)
+    // Signal shutdown
+    if (m_pShutdownEvent != nullptr)
+    {
+        LOG_IF_FAILED(SetEvent(m_pShutdownEvent));
+    }
+
+    // Need to wait for either the app to be initialized, the worker thread to exit, or the shutdown timeout.
+    const HANDLE waitHandles[2] = { m_pInitializeEvent, m_workerThread.native_handle() };
+
+    const auto waitResult = WaitForMultipleObjects(2, waitHandles, FALSE, m_pConfig->QueryShutdownTimeLimitInMS());
+
+    // If waitResults != WAIT_OBJECT_0 + 1, it means main hasn't returned, so okay to call into it.
+    if (!m_blockManagedCallbacks && waitResult != WAIT_OBJECT_0 + 1)
     {
         // We cannot call into managed if the dll is detaching from the process.
         // Calling into managed code when the dll is detaching is strictly a bad idea,
@@ -80,18 +104,17 @@ IN_PROCESS_APPLICATION::StopClr()
         }
     }
 
-    // Signal shutdown
-    if (m_pShutdownEvent != nullptr)
-    {
-        LOG_IF_FAILED(SetEvent(m_pShutdownEvent));
-    }
-
     if (m_workerThread.joinable())
     {
         // Worker thread would wait for clr to finish and log error if required
         m_workerThread.join();
     }
 
+    if (m_folderCleanupThread.joinable())
+    {
+        m_folderCleanupThread.join();
+    }
+
     s_Application = nullptr;
 }
 
@@ -146,12 +169,43 @@ IN_PROCESS_APPLICATION::LoadManagedApplication(ErrorContext& errorContext)
 
     LOG_INFO(L"Waiting for initialization");
 
-    m_workerThread = std::thread([](std::unique_ptr<IN_PROCESS_APPLICATION, IAPPLICATION_DELETER> application)
+    THROW_IF_FAILED(StartMonitoringAppOffline());
+
+    if (!m_shadowCopyDirectory.empty())
     {
-        LOG_INFO(L"Starting in-process worker thread");
-        application->ExecuteApplication();
-        LOG_INFO(L"Stopping in-process worker thread");
-    }, ::ReferenceApplication(this));
+        if (!Environment::CheckUpToDate(QueryApplicationPhysicalPath(), m_shadowCopyDirectory, L".dll", std::filesystem::path(m_shadowCopyDirectory).parent_path()))
+        {
+            Stop(/* fServerInitiated */false);
+            throw InvalidOperationException(L"File changed between copy and start of application, restarting.");
+        }
+        // Cleanup other directories that haven't been removed.
+        m_folderCleanupThread = std::thread([](std::wstring shadowCopyDir)
+            {
+                auto parentDir = std::filesystem::path(shadowCopyDir).parent_path();
+                for (auto& p : std::filesystem::directory_iterator(parentDir))
+                {
+                    if (p.path() != shadowCopyDir)
+                    {
+                        try
+                        {
+                            std::filesystem::remove_all(p.path());
+                        }
+                        catch (...)
+                        {
+                            OBSERVE_CAUGHT_EXCEPTION();
+                        }
+                    }
+                }
+
+            }, m_shadowCopyDirectory);
+    }
+
+    m_workerThread = std::thread([](std::unique_ptr<IN_PROCESS_APPLICATION, IAPPLICATION_DELETER> application)
+        {
+            LOG_INFO(L"Starting in-process worker thread");
+            application->ExecuteApplication();
+            LOG_INFO(L"Stopping in-process worker thread");
+        }, ::ReferenceApplication(this));
 
     const HANDLE waitHandles[2] = { m_pInitializeEvent, m_workerThread.native_handle() };
 
@@ -188,8 +242,6 @@ IN_PROCESS_APPLICATION::LoadManagedApplication(ErrorContext& errorContext)
         throw InvalidOperationException(format(L"CLR worker thread exited prematurely"));
     }
 
-    THROW_IF_FAILED(StartMonitoringAppOffline());
-
     return S_OK;
 }
 
@@ -209,11 +261,11 @@ IN_PROCESS_APPLICATION::ExecuteApplication()
             THROW_IF_FAILED(HostFxrResolutionResult::Create(
                 m_dotnetExeKnownLocation,
                 m_pConfig->QueryProcessPath(),
-                QueryApplicationPhysicalPath(),
+                m_shadowCopyDirectory.empty() ? QueryApplicationPhysicalPath() : m_shadowCopyDirectory,
                 m_pConfig->QueryArguments(),
                 errorContext,
                 hostFxrResolutionResult
-                ));
+            ));
 
             hostFxrResolutionResult->GetArguments(context->m_argc, context->m_argv);
             THROW_IF_FAILED(SetEnvironmentVariablesOnWorkerProcess());
@@ -294,6 +346,11 @@ IN_PROCESS_APPLICATION::ExecuteApplication()
         RETURN_IF_NOT_ZERO(context->m_hostFxr.SetRuntimePropertyValue(DOTNETCORE_USE_ENTRYPOINT_FILTER, L"1"));
         RETURN_IF_NOT_ZERO(context->m_hostFxr.SetRuntimePropertyValue(DOTNETCORE_STACK_SIZE, m_pConfig->QueryStackSize().c_str()));
 
+        if (!m_shadowCopyDirectory.empty())
+        {
+            RETURN_IF_NOT_ZERO(context->m_hostFxr.SetRuntimePropertyValue(APP_CONTEXT_BASE_DIRECTORY, Environment::GetCurrentDirectoryValue().c_str()));
+        }
+
         bool clrThreadExited;
         {
             //Start CLR thread
@@ -393,11 +450,11 @@ void IN_PROCESS_APPLICATION::QueueStop()
     LOG_INFO(L"Queueing in-process stop thread");
 
     std::thread stoppingThread([](std::unique_ptr<IN_PROCESS_APPLICATION, IAPPLICATION_DELETER> application)
-    {
-        LOG_INFO(L"Starting in-process stop thread");
-        application->Stop(false);
-        LOG_INFO(L"Stopping in-process stop thread");
-    }, ::ReferenceApplication(this));
+        {
+            LOG_INFO(L"Starting in-process stop thread");
+            application->Stop(false);
+            LOG_INFO(L"Stopping in-process stop thread");
+        }, ::ReferenceApplication(this));
 
     stoppingThread.detach();
 }
@@ -458,7 +515,7 @@ IN_PROCESS_APPLICATION::ExecuteClr(const std::shared_ptr<ExecuteClrContext>& con
         context->m_exitCode = exitCode;
         context->m_hostFxr.Close();
     }
-    __except(GetExceptionCode() != 0)
+    __except (GetExceptionCode() != 0)
     {
         LOG_INFOF(L"Managed threw an exception %d", GetExceptionCode());
 
@@ -472,7 +529,7 @@ IN_PROCESS_APPLICATION::ExecuteClr(const std::shared_ptr<ExecuteClrContext>& con
 // in case of startup timeout
 //
 VOID
-IN_PROCESS_APPLICATION::ClrThreadEntryPoint(const std::shared_ptr<ExecuteClrContext> &context)
+IN_PROCESS_APPLICATION::ClrThreadEntryPoint(const std::shared_ptr<ExecuteClrContext>& context)
 {
     HandleWrapper<ModuleHandleTraits> moduleHandle;
 
@@ -503,7 +560,7 @@ IN_PROCESS_APPLICATION::SetEnvironmentVariablesOnWorkerProcess()
         QueryApplicationPhysicalPath().c_str(),
         nullptr);
 
-    for (const auto & variable : variables)
+    for (const auto& variable : variables)
     {
         LOG_INFOF(L"Setting environment variable %ls=%ls", variable.first.c_str(), variable.second.c_str());
         SetEnvironmentVariable(variable.first.c_str(), variable.second.c_str());
@@ -537,7 +594,7 @@ IN_PROCESS_APPLICATION::UnexpectedThreadExit(const ExecuteClrContext& context) c
                 QueryApplicationId().c_str(),
                 QueryApplicationPhysicalPath().c_str(),
                 context.m_exceptionCode
-                );
+            );
         }
         return;
     }
@@ -571,13 +628,12 @@ IN_PROCESS_APPLICATION::UnexpectedThreadExit(const ExecuteClrContext& context) c
 
 HRESULT
 IN_PROCESS_APPLICATION::CreateHandler(
-    _In_  IHttpContext       *pHttpContext,
-    _Out_ IREQUEST_HANDLER  **pRequestHandler)
+    _In_  IHttpContext* pHttpContext,
+    _Out_ IREQUEST_HANDLER** pRequestHandler)
 {
     try
     {
         SRWSharedLock dataLock(m_dataLock);
-
         DBG_ASSERT(!m_fStopCalled);
         m_requestCount++;
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.h b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.h
index 4eda1fd7dadc..2cefb9bbcd04 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/InProcessRequestHandler/inprocessapplication.h
@@ -145,6 +145,8 @@ class IN_PROCESS_APPLICATION : public InProcessApplicationBase
     std::thread                     m_clrThread;
     // Thread tracking the CLR thread, this one is always joined on shutdown
     std::thread                     m_workerThread;
+    // Thread for cleaning up existing shadow copy folders
+    std::thread                     m_folderCleanupThread;
     // The event that gets triggered when managed initialization is complete
     HandleWrapper<NullHandleTraits> m_pInitializeEvent;
     // The event that gets triggered when worker thread should exit
@@ -177,6 +179,7 @@ class IN_PROCESS_APPLICATION : public InProcessApplicationBase
     std::shared_ptr<StringStreamRedirectionOutput> m_stringRedirectionOutput;
 
     inline static const LPCSTR      s_exeLocationParameterName = "InProcessExeLocation";
+    inline static const LPCSTR      s_shadowCopyDirectoryName = "ShadowCopyDirectory";
 
     VOID
     UnexpectedThreadExit(const ExecuteClrContext& context) const;
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/outprocessapplication.cpp b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/outprocessapplication.cpp
index 7bd0a5fa83bf..897a97d17c05 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/outprocessapplication.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/OutOfProcessRequestHandler/outprocessapplication.cpp
@@ -2,7 +2,6 @@
 // Licensed under the MIT License. See License.txt in the project root for license information.
 
 #include "outprocessapplication.h"
-
 #include "SRWExclusiveLock.h"
 #include "exceptions.h"
 
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.cpp b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.cpp
index a946e7c2dc5a..e7dbdf196d47 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.cpp
@@ -25,13 +25,13 @@ HRESULT AppOfflineTrackingApplication::StartMonitoringAppOffline()
 
 void AppOfflineTrackingApplication::StopInternal(bool fServerInitiated)
 {
-    APPLICATION::StopInternal(fServerInitiated);
-
     if (m_fileWatcher)
     {
         m_fileWatcher->StopMonitor();
         m_fileWatcher = nullptr;
     }
+
+    APPLICATION::StopInternal(fServerInitiated);
 }
 
 HRESULT AppOfflineTrackingApplication::StartMonitoringAppOflineImpl()
@@ -44,7 +44,9 @@ HRESULT AppOfflineTrackingApplication::StartMonitoringAppOflineImpl()
     m_fileWatcher = std::make_unique<FILE_WATCHER>();
     RETURN_IF_FAILED(m_fileWatcher->Create(m_applicationPath.c_str(),
         L"app_offline.htm",
-        this));
+        m_shadowCopyDirectory,
+        this,
+        m_shutdownTimeout));
 
     return S_OK;
 }
@@ -56,11 +58,22 @@ void AppOfflineTrackingApplication::OnAppOffline()
         return;
     }
 
-    LOG_INFOF(L"Received app_offline notification in application '%ls'", m_applicationPath.c_str());
-    EventLog::Info(
-        ASPNETCORE_EVENT_RECYCLE_APPOFFLINE,
-        ASPNETCORE_EVENT_RECYCLE_APPOFFLINE_MSG,
-        m_applicationPath.c_str());
+    if (m_detectedAppOffline)
+    {
+        LOG_INFOF(L"Received app_offline notification in application '%ls'", m_applicationPath.c_str());
+        EventLog::Info(
+            ASPNETCORE_EVENT_RECYCLE_APPOFFLINE,
+            ASPNETCORE_EVENT_RECYCLE_APPOFFLINE_MSG,
+            m_applicationPath.c_str());
+    }
+    else
+    {
+        LOG_INFOF(L"Received file change notification in application '%ls'", m_applicationPath.c_str());
+        EventLog::Info(
+            ASPNETCORE_EVENT_RECYCLE_APPOFFLINE,
+            ASPNETCORE_EVENT_RECYCLE_FILECHANGE_MSG,
+            m_applicationPath.c_str());
+    }
 
     Stop(/*fServerInitiated*/ false);
 }
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.h b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.h
index b504a730fd62..8d4eafc0aad0 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/AppOfflineTrackingApplication.h
@@ -15,7 +15,8 @@ class AppOfflineTrackingApplication: public APPLICATION
         : APPLICATION(application),
         m_applicationPath(application.GetApplicationPhysicalPath()),
         m_fileWatcher(nullptr),
-        m_fAppOfflineProcessed(false)
+        m_fAppOfflineProcessed(false),
+        m_shutdownTimeout(120000) // default to 2 minutes
     {
     }
 
@@ -37,6 +38,10 @@ class AppOfflineTrackingApplication: public APPLICATION
     VOID
     OnAppOffline();
 
+    // TODO protected
+    bool                                         m_detectedAppOffline;
+    std::wstring                                 m_shadowCopyDirectory;
+    DWORD                                        m_shutdownTimeout;
 private:
     HRESULT
     StartMonitoringAppOflineImpl();
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.cpp b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.cpp
index 9d17f95b37c3..f4baec9f40d2 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.cpp
@@ -6,21 +6,32 @@
 #include "debugutil.h"
 #include "AppOfflineTrackingApplication.h"
 #include "exceptions.h"
+#include <EventLog.h>
 
 FILE_WATCHER::FILE_WATCHER() :
     m_hCompletionPort(NULL),
     m_hChangeNotificationThread(NULL),
-    m_fThreadExit(FALSE)
+    m_fThreadExit(FALSE),
+    m_fShadowCopyEnabled(FALSE),
+    m_copied(false)
 {
+    m_pDoneCopyEvent = CreateEvent(
+        nullptr,  // default security attributes
+        TRUE,     // manual reset event
+        FALSE,    // not set
+        nullptr); // name
 }
 
 FILE_WATCHER::~FILE_WATCHER()
 {
     StopMonitor();
+    WaitForMonitor(20); // wait for 1 second total
+}
 
+void FILE_WATCHER::WaitForMonitor(DWORD dwRetryCounter)
+{
     if (m_hChangeNotificationThread != NULL)
     {
-        DWORD dwRetryCounter = 20;      // totally wait for 1s
         DWORD dwExitCode = STILL_ACTIVE;
 
         while (!m_fThreadExit && dwRetryCounter > 0)
@@ -54,9 +65,14 @@ HRESULT
 FILE_WATCHER::Create(
     _In_ PCWSTR                  pszDirectoryToMonitor,
     _In_ PCWSTR                  pszFileNameToMonitor,
-    _In_ AppOfflineTrackingApplication *pApplication
+    _In_ const std::wstring&     shadowCopyPath,
+    _In_ AppOfflineTrackingApplication* pApplication,
+    _In_ DWORD                   shutdownTimeout
 )
 {
+    m_shadowCopyPath = shadowCopyPath;
+    m_fShadowCopyEnabled = !shadowCopyPath.empty();
+    m_shutdownTimeout = shutdownTimeout;
 
     RETURN_LAST_ERROR_IF_NULL(m_hCompletionPort = CreateIoCompletionPort(INVALID_HANDLE_VALUE, NULL, 0, 0));
 
@@ -130,10 +146,10 @@ Win32 error
 
 --*/
 {
-    FILE_WATCHER *       pFileMonitor;
+    FILE_WATCHER* pFileMonitor;
     BOOL                 fSuccess = FALSE;
     DWORD                cbCompletion = 0;
-    OVERLAPPED *         pOverlapped = NULL;
+    OVERLAPPED* pOverlapped = NULL;
     DWORD                dwErrorStatus;
     ULONG_PTR            completionKey;
 
@@ -177,7 +193,15 @@ Win32 error
 
     pFileMonitor->m_fThreadExit = TRUE;
 
+    if (pFileMonitor->m_fShadowCopyEnabled)
+    {
+        // Cancel the timer to avoid it calling copy.
+        pFileMonitor->m_Timer.CancelTimer();
+        FILE_WATCHER::CopyAndShutdown(pFileMonitor);
+    }
+
     LOG_INFO(L"Stopping file watcher thread");
+
     ExitThread(0);
 }
 
@@ -204,7 +228,8 @@ HRESULT
 
 --*/
 {
-    BOOL                        fFileChanged = FALSE;
+    BOOL                        fAppOfflineChanged = FALSE;
+    BOOL                        fDllChanged = FALSE;
 
     // When directory handle is closed then HandleChangeCompletion
     // happens with cbCompletion = 0 and dwCompletionStatus = 0
@@ -226,7 +251,7 @@ HRESULT
     //
     if (cbCompletion == 0)
     {
-        fFileChanged = TRUE;
+        fAppOfflineChanged = TRUE;
     }
     else
     {
@@ -242,9 +267,22 @@ HRESULT
                 _strFileName.QueryStr(),
                 pNotificationInfo->FileNameLength / sizeof(WCHAR)) == 0)
             {
-                fFileChanged = TRUE;
+                fAppOfflineChanged = TRUE;
+                auto app = _pApplication.get();
+                app->m_detectedAppOffline = true;
                 break;
             }
+
+            //
+            // Look for changes to dlls when shadow copying is enabled.
+            //
+            std::wstring notification(pNotificationInfo->FileName, pNotificationInfo->FileNameLength / sizeof(WCHAR));
+            std::filesystem::path notificationPath(notification);
+            if (m_fShadowCopyEnabled && notificationPath.extension().compare(L".dll") == 0)
+            {
+                fDllChanged = TRUE;
+            }
+
             //
             // Advance to next notification
             //
@@ -261,16 +299,92 @@ HRESULT
         }
     }
 
-    if (fFileChanged && !_lStopMonitorCalled)
+    if (fAppOfflineChanged && !_lStopMonitorCalled)
     {
         // Reference application before
         _pApplication->ReferenceApplication();
         RETURN_LAST_ERROR_IF(!QueueUserWorkItem(RunNotificationCallback, _pApplication.get(), WT_EXECUTEDEFAULT));
     }
 
+    if (fDllChanged && m_fShadowCopyEnabled && !_lStopMonitorCalled)
+    {
+        // Reset timer for dll checks
+        LOG_INFO(L"Detected dll change, resetting timer callback which will eventually trigger shutdown.");
+        m_Timer.CancelTimer();
+        m_Timer.InitializeTimer(FILE_WATCHER::TimerCallback, this, 5000, INFINITE);
+    }
+
     return S_OK;
 }
 
+
+VOID
+CALLBACK
+FILE_WATCHER::TimerCallback(
+    _In_ PTP_CALLBACK_INSTANCE Instance,
+    _In_ PVOID Context,
+    _In_ PTP_TIMER Timer
+)
+{
+    Instance;
+    Timer;
+    CopyAndShutdown((FILE_WATCHER*)Context);
+}
+
+DWORD WINAPI FILE_WATCHER::CopyAndShutdown(FILE_WATCHER* watcher)
+{
+    // Only copy and shutdown once
+    SRWExclusiveLock lock(watcher->m_copyLock);
+    if (watcher->m_copied)
+    {
+        return 0;
+    }
+
+    watcher->m_copied = true;
+
+    LOG_INFO(L"Starting copy on shutdown in filewatcher, creating directory.");
+
+    auto directoryNameInt = 0;
+    auto currentShadowCopyDirectory = std::filesystem::path(watcher->m_shadowCopyPath);
+    auto parentDirectory = currentShadowCopyDirectory.parent_path();
+    try
+    {
+        directoryNameInt = std::stoi(currentShadowCopyDirectory.filename().string());
+    }
+    catch (...)
+    {
+        OBSERVE_CAUGHT_EXCEPTION();
+        return 0;
+    }
+
+    // Add one to the directory we want to copy to.
+    directoryNameInt++;
+    auto destination = parentDirectory / std::to_wstring(directoryNameInt);
+
+    LOG_INFOF(L"Copying new shadow copy directory to %ls.", destination.wstring().c_str());
+
+    // Copy contents before shutdown
+    try
+    {
+        Environment::CopyToDirectory(watcher->_strDirectoryName.QueryStr(), destination, false, std::filesystem::canonical(parentDirectory));
+    }
+    catch (...)
+    {
+        OBSERVE_CAUGHT_EXCEPTION();
+        return 0;
+    }
+
+    LOG_INFOF(L"Finished copy on shutdown to %ls.", destination.wstring().c_str());
+
+    SetEvent(watcher->m_pDoneCopyEvent);
+
+    // reference application before callback (same thing we do with app_offline).
+    watcher->_pApplication->ReferenceApplication();
+    QueueUserWorkItem(RunNotificationCallback, watcher->_pApplication.get(), WT_EXECUTEDEFAULT);
+
+    return 0;
+}
+
 DWORD
 WINAPI
 FILE_WATCHER::RunNotificationCallback(
@@ -279,7 +393,6 @@ FILE_WATCHER::RunNotificationCallback(
 {
     // Recapture application instance into unique_ptr
     auto pApplication = std::unique_ptr<AppOfflineTrackingApplication, IAPPLICATION_DELETER>(static_cast<AppOfflineTrackingApplication*>(pvArg));
-    DBG_ASSERT(pFileMonitor != NULL);
     pApplication->OnAppOffline();
 
     return 0;
@@ -319,9 +432,23 @@ FILE_WATCHER::StopMonitor()
     // we know that HandleChangeCompletion() call
     // can be ignored
     //
-    InterlockedExchange(&_lStopMonitorCalled, 1);
+    if (InterlockedExchange(&_lStopMonitorCalled, 1) == 1)
+    {
+        return;
+    }
+
+    LOG_INFO(L"Stopping file watching.");
+
     // signal the file watch thread to exit
     PostQueuedCompletionStatus(m_hCompletionPort, 0, FILE_WATCHER_SHUTDOWN_KEY, NULL);
+    WaitForMonitor(200);
+
+    if (m_fShadowCopyEnabled)
+    {
+        // If we are shadow copying, wait for the copying to finish.
+        WaitForSingleObject(m_pDoneCopyEvent, m_shutdownTimeout);
+    }
+
     // Release application reference
     _pApplication.reset(nullptr);
 }
diff --git a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.h b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.h
index 46ea74453322..470edbb5eb21 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.h
+++ b/src/Servers/IIS/AspNetCoreModuleV2/RequestHandlerLib/filewatcher.h
@@ -8,6 +8,8 @@
 #include <functional>
 #include "iapplication.h"
 #include "HandleWrapper.h"
+#include "Environment.h"
+#include <sttimer.h>
 
 #define FILE_WATCHER_SHUTDOWN_KEY           (ULONG_PTR)(-1)
 #define FILE_WATCHER_ENTRY_BUFFER_SIZE      4096
@@ -22,10 +24,14 @@ class FILE_WATCHER{
 
     ~FILE_WATCHER();
 
+    void WaitForMonitor(DWORD dwRetryCounter);
+
     HRESULT Create(
         _In_ PCWSTR                  pszDirectoryToMonitor,
         _In_ PCWSTR                  pszFileNameToMonitor,
-        _In_ AppOfflineTrackingApplication *pApplication
+        _In_ const std::wstring&            shadowCopyPath,
+        _In_ AppOfflineTrackingApplication *pApplication,
+        _In_ DWORD                   shutdownTimeout
     );
 
     static
@@ -36,6 +42,14 @@ class FILE_WATCHER{
     DWORD
     WINAPI RunNotificationCallback(LPVOID);
 
+    static
+    VOID
+    WINAPI TimerCallback(_In_ PTP_CALLBACK_INSTANCE Instance,
+        _In_ PVOID Context,
+        _In_ PTP_TIMER Timer);
+
+    static DWORD WINAPI CopyAndShutdown(FILE_WATCHER* watcher);
+
     HRESULT HandleChangeCompletion(DWORD cbCompletion);
 
     HRESULT Monitor();
@@ -45,13 +59,20 @@ class FILE_WATCHER{
     HandleWrapper<NullHandleTraits>               m_hCompletionPort;
     HandleWrapper<NullHandleTraits>               m_hChangeNotificationThread;
     HandleWrapper<NullHandleTraits>               _hDirectory;
+    HandleWrapper<NullHandleTraits> m_pDoneCopyEvent;
     volatile   BOOL      m_fThreadExit;
+    STTIMER                 m_Timer;
+    SRWLOCK                 m_copyLock{};
+    BOOL                    m_copied;
 
     BUFFER                  _buffDirectoryChanges;
     STRU                    _strFileName;
     STRU                    _strDirectoryName;
     STRU                    _strFullName;
     LONG                    _lStopMonitorCalled {};
+    bool                    m_fShadowCopyEnabled;
+    std::wstring            m_shadowCopyPath;
+    DWORD                   m_shutdownTimeout;
     OVERLAPPED              _overlapped;
     std::unique_ptr<AppOfflineTrackingApplication, IAPPLICATION_DELETER> _pApplication;
 };
diff --git a/src/Servers/IIS/IIS/perf/Microbenchmarks/Properties/launchSettings.json b/src/Servers/IIS/IIS/perf/Microbenchmarks/Properties/launchSettings.json
new file mode 100644
index 000000000000..fe76b29b53d8
--- /dev/null
+++ b/src/Servers/IIS/IIS/perf/Microbenchmarks/Properties/launchSettings.json
@@ -0,0 +1,40 @@
+{
+  "iisSettings": {
+    "windowsAuthentication": true,
+    "anonymousAuthentication": true,
+    "iisExpress": {
+      "applicationUrl": "http://localhost:5762/",
+      "sslPort": 0
+    }
+  },
+  "profiles": {
+    "ANCM IIS Express": {
+      "commandName": "Executable",
+      "executablePath": "$(IISExpressPath)",
+      "commandLineArgs": "$(IISExpressArguments)",
+      "environmentVariables": {
+        "IIS_SITE_PATH": "$(MSBuildThisFileDirectory)",
+        "ANCMV2_PATH": "$(AspNetCoreModuleV2ShimDll)",
+        "ASPNETCORE_MODULE_OUTOFPROCESS_HANDLER": "$(AspNetCoreModuleV2OutOfProcessHandlerDll)",
+        "LAUNCHER_ARGS": "$(TargetPath)",
+        "ASPNETCORE_ENVIRONMENT": "Development",
+        "LAUNCHER_PATH": "$(DotNetPath)",
+        "ASPNETCORE_MODULE_DEBUG": "console"
+      }
+    },
+    "ANCM IIS": {
+      "commandName": "Executable",
+      "executablePath": "$(IISPath)",
+      "commandLineArgs": "$(IISArguments)",
+      "environmentVariables": {
+        "IIS_SITE_PATH": "$(MSBuildThisFileDirectory)",
+        "ANCMV2_PATH": "$(AspNetCoreModuleV2ShimDll)",
+        "ASPNETCORE_MODULE_OUTOFPROCESS_HANDLER": "$(AspNetCoreModuleV2OutOfProcessHandlerDll)",
+        "LAUNCHER_ARGS": "$(TargetPath)",
+        "ASPNETCORE_ENVIRONMENT": "Development",
+        "LAUNCHER_PATH": "$(DotNetPath)",
+        "ASPNETCORE_MODULE_DEBUG": "console"
+      }
+    }
+  }
+}
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Infrastructure/EventLogHelpers.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Infrastructure/EventLogHelpers.cs
index 9332b5deb61c..744ea078193c 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Infrastructure/EventLogHelpers.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Infrastructure/EventLogHelpers.cs
@@ -167,6 +167,11 @@ public static string InProcessShutdown()
             return "Application 'MACHINE/WEBROOT/APPHOST/.*?' has shutdown.";
         }
 
+        public static string ShutdownFileChange(IISDeploymentResult deploymentResult)
+        {
+            return $"Application '{EscapedContentRoot(deploymentResult)}' was recycled after detecting file change in application directory.";
+        }
+
         public static string InProcessFailedToStop(IISDeploymentResult deploymentResult, string reason)
         {
             return "Failed to gracefully shutdown application 'MACHINE/WEBROOT/APPHOST/.*?'.";
diff --git a/src/Servers/IIS/IIS/test/IIS.FunctionalTests/ShadowCopyTests.cs b/src/Servers/IIS/IIS/test/IIS.FunctionalTests/ShadowCopyTests.cs
new file mode 100644
index 000000000000..fed5da275e4a
--- /dev/null
+++ b/src/Servers/IIS/IIS/test/IIS.FunctionalTests/ShadowCopyTests.cs
@@ -0,0 +1,261 @@
+// Copyright (c) .NET Foundation. All rights reserved.
+// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
+
+using System;
+using System.IO;
+using System.Threading.Tasks;
+using Microsoft.AspNetCore.Server.IIS.FunctionalTests.Utilities;
+using Microsoft.AspNetCore.Testing;
+using Xunit;
+
+namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
+{
+    [Collection(PublishedSitesCollection.Name)]
+    public class ShadowCopyTests : IISFunctionalTestBase
+    {
+        public ShadowCopyTests(PublishedSitesFixture fixture) : base(fixture)
+        {
+        }
+
+        [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H2, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
+        public async Task ShadowCopyDoesNotLockFiles()
+        {
+            using var directory = TempDirectory.Create();
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+            deploymentParameters.HandlerSettings["experimentalEnableShadowCopy"] = "true";
+            deploymentParameters.HandlerSettings["shadowCopyDirectory"] = directory.DirectoryPath;
+
+            var deploymentResult = await DeployAsync(deploymentParameters);
+            var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+
+            Assert.True(response.IsSuccessStatusCode);
+            var directoryInfo = new DirectoryInfo(deploymentResult.ContentRoot);
+
+            // Verify that we can delete all files in the content root (nothing locked)
+            foreach (var fileInfo in directoryInfo.GetFiles())
+            {
+                fileInfo.Delete();
+            }
+
+            foreach (var dirInfo in directoryInfo.GetDirectories())
+            {
+                dirInfo.Delete(recursive: true);
+            }
+        }
+
+        [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H2, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
+        public async Task ShadowCopyRelativeInSameDirectoryWorks()
+        {
+            var directoryName = Path.GetRandomFileName();
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+            deploymentParameters.HandlerSettings["experimentalEnableShadowCopy"] = "true";
+            deploymentParameters.HandlerSettings["shadowCopyDirectory"] = directoryName;
+
+            var deploymentResult = await DeployAsync(deploymentParameters);
+            var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+
+            Assert.True(response.IsSuccessStatusCode);
+            var directoryInfo = new DirectoryInfo(deploymentResult.ContentRoot);
+
+            // Verify that we can delete all files in the content root (nothing locked)
+            foreach (var fileInfo in directoryInfo.GetFiles())
+            {
+                fileInfo.Delete();
+            }
+
+            var tempDirectoryPath = Path.Combine(deploymentResult.ContentRoot, directoryName);
+            foreach (var dirInfo in directoryInfo.GetDirectories())
+            {
+                if (!tempDirectoryPath.Equals(dirInfo.FullName))
+                {
+                    dirInfo.Delete(recursive: true);
+                }
+            }
+        }
+
+        [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H2, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
+        public async Task ShadowCopyRelativeOutsideDirectoryWorks()
+        {
+            using var directory = TempDirectory.Create();
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+            deploymentParameters.HandlerSettings["experimentalEnableShadowCopy"] = "true";
+            deploymentParameters.HandlerSettings["shadowCopyDirectory"] = $"..\\{directory.DirectoryInfo.Name}";
+            deploymentParameters.ApplicationPath = directory.DirectoryPath;
+
+            var deploymentResult = await DeployAsync(deploymentParameters);
+            var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+
+            // Check if directory can be deleted.
+            // Can't delete the folder but can delete all content in it.
+
+            Assert.True(response.IsSuccessStatusCode);
+            var directoryInfo = new DirectoryInfo(deploymentResult.ContentRoot);
+
+            // Verify that we can delete all files in the content root (nothing locked)
+            foreach (var fileInfo in directoryInfo.GetFiles())
+            {
+                fileInfo.Delete();
+            }
+
+            foreach (var dirInfo in directoryInfo.GetDirectories())
+            {
+                dirInfo.Delete(recursive: true);
+            }
+
+            StopServer();
+            deploymentResult.AssertWorkerProcessStop();
+        }
+
+        [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H2, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
+        public async Task ShadowCopySingleFileChangedWorks()
+        {
+            using var directory = TempDirectory.Create();
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+            deploymentParameters.HandlerSettings["experimentalEnableShadowCopy"] = "true";
+            deploymentParameters.HandlerSettings["shadowCopyDirectory"] = directory.DirectoryPath;
+
+            var deploymentResult = await DeployAsync(deploymentParameters);
+
+            DirectoryCopy(deploymentResult.ContentRoot, directory.DirectoryPath, copySubDirs: true);
+
+            var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+            Assert.True(response.IsSuccessStatusCode);
+            // Rewrite file
+            var dirInfo = new DirectoryInfo(deploymentResult.ContentRoot);
+
+            string dllPath = "";
+            foreach (var file in dirInfo.EnumerateFiles())
+            {
+                if (file.Extension == ".dll")
+                {
+                    dllPath = file.FullName;
+                    break;
+                }
+            }
+            var fileContents = File.ReadAllBytes(dllPath);
+            File.WriteAllBytes(dllPath, fileContents);
+
+            deploymentResult.AssertWorkerProcessStop();
+
+            response = await deploymentResult.HttpClient.GetAsync("Wow!");
+            Assert.True(response.IsSuccessStatusCode);
+        }
+
+        [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H2, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
+        public async Task ShadowCopyE2EWorksWithFolderPresent()
+        {
+            using var directory = TempDirectory.Create();
+            var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+            deploymentParameters.HandlerSettings["experimentalEnableShadowCopy"] = "true";
+            deploymentParameters.HandlerSettings["shadowCopyDirectory"] = directory.DirectoryPath;
+            var deploymentResult = await DeployAsync(deploymentParameters);
+
+            DirectoryCopy(deploymentResult.ContentRoot, Path.Combine(directory.DirectoryPath, "0"), copySubDirs: true);
+
+            var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+            Assert.True(response.IsSuccessStatusCode);
+
+            using var secondTempDir = TempDirectory.Create();
+
+            // copy back and forth to cause file change notifications.
+            DirectoryCopy(deploymentResult.ContentRoot, secondTempDir.DirectoryPath, copySubDirs: true);
+            DirectoryCopy(secondTempDir.DirectoryPath, deploymentResult.ContentRoot, copySubDirs: true);
+
+            deploymentResult.AssertWorkerProcessStop();
+            response = await deploymentResult.HttpClient.GetAsync("Wow!");
+            Assert.True(response.IsSuccessStatusCode);
+        }
+
+        public class TempDirectory : IDisposable
+        {
+            public static TempDirectory Create()
+            {
+                var directoryPath = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+                var directoryInfo = Directory.CreateDirectory(directoryPath);
+                return new TempDirectory(directoryInfo);
+            }
+
+            public TempDirectory(DirectoryInfo directoryInfo)
+            {
+                DirectoryInfo = directoryInfo;
+
+                DirectoryPath = directoryInfo.FullName;
+            }
+
+            public string DirectoryPath { get; }
+            public DirectoryInfo DirectoryInfo { get; }
+
+            public void Dispose()
+            {
+                DeleteDirectory(DirectoryPath);
+            }
+
+            private static void DeleteDirectory(string directoryPath)
+            {
+                foreach (var subDirectoryPath in Directory.EnumerateDirectories(directoryPath))
+                {
+                    DeleteDirectory(subDirectoryPath);
+                }
+
+                try
+                {
+                    foreach (var filePath in Directory.EnumerateFiles(directoryPath))
+                    {
+                        var fileInfo = new FileInfo(filePath)
+                        {
+                            Attributes = FileAttributes.Normal
+                        };
+                        fileInfo.Delete();
+                    }
+                    Directory.Delete(directoryPath);
+                }
+                catch (Exception e)
+                {
+                    Console.WriteLine($@"Failed to delete directory {directoryPath}: {e.Message}");
+                }
+            }
+        }
+
+        // copied from https://docs.microsoft.com/en-us/dotnet/standard/io/how-to-copy-directories
+        private static void DirectoryCopy(string sourceDirName, string destDirName, bool copySubDirs)
+        {
+            // Get the subdirectories for the specified directory.
+            DirectoryInfo dir = new DirectoryInfo(sourceDirName);
+
+            if (!dir.Exists)
+            {
+                throw new DirectoryNotFoundException(
+                    "Source directory does not exist or could not be found: "
+                    + sourceDirName);
+            }
+
+            DirectoryInfo[] dirs = dir.GetDirectories();
+
+            // If the destination directory doesn't exist, create it.
+            Directory.CreateDirectory(destDirName);
+
+            // Get the files in the directory and copy them to the new location.
+            FileInfo[] files = dir.GetFiles();
+            foreach (FileInfo file in files)
+            {
+                string tempPath = Path.Combine(destDirName, file.Name);
+                file.CopyTo(tempPath, true);
+            }
+
+            // If copying subdirectories, copy them and their contents to new location.
+            if (copySubDirs)
+            {
+                foreach (DirectoryInfo subdir in dirs)
+                {
+                    string tempPath = Path.Combine(destDirName, subdir.Name);
+                    DirectoryCopy(subdir.FullName, tempPath, copySubDirs);
+                }
+            }
+        }
+    }
+}
diff --git a/src/Servers/IIS/IISIntegration.slnf b/src/Servers/IIS/IISIntegration.slnf
index e8ce42f08921..f5f7ddf1ec9a 100644
--- a/src/Servers/IIS/IISIntegration.slnf
+++ b/src/Servers/IIS/IISIntegration.slnf
@@ -36,6 +36,7 @@
       "src\\Servers\\IIS\\IIS\\perf\\Microbenchmarks\\IIS.Microbenchmarks.csproj",
       "src\\Servers\\IIS\\IIS\\samples\\NativeIISSample\\NativeIISSample.csproj",
       "src\\Servers\\IIS\\IIS\\src\\Microsoft.AspNetCore.Server.IIS.csproj",
+      "src\\Servers\\IIS\\IIS\\samples\\NativeIISSample\\NativeIISSample.csproj",
       "src\\Servers\\IIS\\IIS\\test\\IIS.FunctionalTests\\IIS.FunctionalTests.csproj",
       "src\\Servers\\IIS\\IIS\\test\\IIS.NewHandler.FunctionalTests\\IIS.NewHandler.FunctionalTests.csproj",
       "src\\Servers\\IIS\\IIS\\test\\IIS.NewShim.FunctionalTests\\IIS.NewShim.FunctionalTests.csproj",