diff --git a/interface/src/Application.cpp b/interface/src/Application.cpp
index e0ac3df30d..9ba886fcd2 100644
--- a/interface/src/Application.cpp
+++ b/interface/src/Application.cpp
@@ -74,6 +74,7 @@
 #include <Midi.h>
 #include <AudioInjectorManager.h>
 #include <AvatarBookmarks.h>
+#include <CrashHelpers.h>
 #include <CursorManager.h>
 #include <VirtualPadManager.h>
 #include <DebugDraw.h>
@@ -2679,6 +2680,8 @@ void Application::updateHeartbeat() const {
 }
 
 void Application::onAboutToQuit() {
+    setCrashAnnotation("shutdown", "1");
+
     // quickly save AvatarEntityData before the EntityTree is dismantled
     getMyAvatar()->saveAvatarEntityDataToSettings();
 
@@ -2717,6 +2720,11 @@ void Application::onAboutToQuit() {
 
     cleanupBeforeQuit();
 
+    if (_crashOnShutdown) {
+        // triggered by crash menu
+        crash::nullDeref();
+    }
+
     getRefreshRateManager().setRefreshRateRegime(RefreshRateManager::RefreshRateRegime::SHUTDOWN);
 }
 
@@ -9527,6 +9535,14 @@ void Application::showUrlHandler(const QUrl& url) {
         }
     });
 }
+
+// used to test "shutdown" crash annotation.
+void Application::crashOnShutdown() {
+    qDebug() << "crashOnShutdown(), ON PURPOSE!";
+    _crashOnShutdown = true;
+    quit();
+}
+
 void Application::overrideEntry(){
     _overrideEntry = true;
 }
diff --git a/interface/src/Application.h b/interface/src/Application.h
index 913671473d..20abbf2baf 100644
--- a/interface/src/Application.h
+++ b/interface/src/Application.h
@@ -497,6 +497,9 @@ public slots:
     bool gpuTextureMemSizeStable();
     void showUrlHandler(const QUrl& url);
 
+    // used to test "shutdown" crash annotation.
+    void crashOnShutdown();
+
 private slots:
     void onDesktopRootItemCreated(QQuickItem* qmlContext);
     void onDesktopRootContextCreated(QQmlContext* qmlContext);
@@ -844,5 +847,7 @@ private:
     bool _overrideEntry { false };
 
     VisionSqueeze _visionSqueeze;
+
+    bool _crashOnShutdown { false };
 };
 #endif // hifi_Application_h
diff --git a/interface/src/Menu.cpp b/interface/src/Menu.cpp
index 4cf78c23ee..8c6292681b 100644
--- a/interface/src/Menu.cpp
+++ b/interface/src/Menu.cpp
@@ -763,6 +763,8 @@ Menu::Menu() {
     action = addActionToQMenuAndActionHash(crashMenu, MenuOption::CrashNewFaultThreaded);
     connect(action, &QAction::triggered, qApp, []() { std::thread(crash::newFault).join(); });
 
+    addActionToQMenuAndActionHash(crashMenu, MenuOption::CrashOnShutdown, 0, qApp, SLOT(crashOnShutdown()));
+
     // Developer > Show Statistics
     addCheckableActionToQMenuAndActionHash(developerMenu, MenuOption::Stats, 0, true);
 
diff --git a/interface/src/Menu.h b/interface/src/Menu.h
index 70687786a9..7dff264adc 100644
--- a/interface/src/Menu.h
+++ b/interface/src/Menu.h
@@ -72,6 +72,7 @@ namespace MenuOption {
     const QString CrashNullDereferenceThreaded = "Null Dereference (threaded)";
     const QString CrashAbort = "Abort";
     const QString CrashAbortThreaded = "Abort (threaded)";
+    const QString CrashOnShutdown = "Crash During Shutdown";
     const QString CrashOutOfBoundsVectorAccess = "Out of Bounds Vector Access";
     const QString CrashOutOfBoundsVectorAccessThreaded = "Out of Bounds Vector Access (threaded)";
     const QString CrashNewFault = "New Fault";