diff --git a/interface/resources/qml/LoginDialog.qml b/interface/resources/qml/LoginDialog.qml
index 227fce3454..336858502d 100644
--- a/interface/resources/qml/LoginDialog.qml
+++ b/interface/resources/qml/LoginDialog.qml
@@ -85,13 +85,4 @@ ModalWindow {
                 break
         }
     }
-    Component.onDestruction: {
-        if (closeButtonVisible && clickedCloseButton && Settings.getValue("loginDialogPoppedUp", false)) {
-            var data = {
-                "action": "opted out"
-            };
-            UserActivityLogger.logAction("encourageLoginDialog", data);
-        }
-        Settings.setValue("loginDialogPoppedUp", false);
-    }
 }
diff --git a/interface/resources/qml/LoginDialog/LinkAccountBody.qml b/interface/resources/qml/LoginDialog/LinkAccountBody.qml
index d19837a023..f7216584e0 100644
--- a/interface/resources/qml/LoginDialog/LinkAccountBody.qml
+++ b/interface/resources/qml/LoginDialog/LinkAccountBody.qml
@@ -350,11 +350,23 @@ Item {
                 bodyLoader.item.width = root.pane.width
                 bodyLoader.item.height = root.pane.height
             }
+            if (Settings.getValue("loginDialogPoppedUp", false)) {
+                var data = {
+                    "action": "user logged in"
+                };
+                UserActivityLogger.logAction("encourageLoginDialog", data);
+            }
         }
         onHandleLoginFailed: {
             console.log("Login Failed")
             mainTextContainer.visible = true
             toggleLoading(false)
+            if (Settings.getValue("loginDialogPoppedUp", false)) {
+                var data = {
+                    "action": "user failed logging in"
+                };
+                UserActivityLogger.logAction("encourageLoginDialog", data);
+            }
         }
         onHandleLinkCompleted: {
             console.log("Link Succeeded")
diff --git a/interface/src/Application.cpp b/interface/src/Application.cpp
index 7f437e273c..de788de99f 100644
--- a/interface/src/Application.cpp
+++ b/interface/src/Application.cpp
@@ -2309,16 +2309,14 @@ Application::Application(int& argc, char** argv, QElapsedTimer& startupTimer, bo
         auto accountManager = DependencyManager::get<AccountManager>();
         auto dialogsManager = DependencyManager::get<DialogsManager>();
         if (!accountManager->isLoggedIn() && !qApp->isHMDMode()) {
-            Settings settings;
-            settings.setValue("loginDialogPoppedUp", true);
+            Setting::Handle<bool>{"loginDialogPoppedUp", false}.set(true);
             dialogsManager->showLoginDialog();
             QJsonObject loginData = {};
             loginData["action"] = "login dialog shown";
             UserActivityLogger::getInstance().logAction("encourageLoginDialog", loginData);
         }
     });
-    Settings settings;
-    settings.setValue("loginDialogPoppedUp", false);
+    Setting::Handle<bool>{"loginDialogPoppedUp", false}.set(false);
     checkLoginTimer->start();
 }
 
@@ -2453,6 +2451,8 @@ void Application::onAboutToQuit() {
     // so its persisted explicitly here
     Setting::Handle<QString>{ ACTIVE_DISPLAY_PLUGIN_SETTING_NAME }.set(getActiveDisplayPlugin()->getName());
 
+    Setting::Handle<bool>{"loginDialogPoppedUp", false}.set(false);
+
     getActiveDisplayPlugin()->deactivate();
     if (_autoSwitchDisplayModeSupportedHMDPlugin
         && _autoSwitchDisplayModeSupportedHMDPlugin->isSessionActive()) {
@@ -4949,9 +4949,6 @@ void Application::loadSettings() {
 }
 
 void Application::saveSettings() const {
-    Settings settings;
-    settings.setValue("loginDialogPoppedUp", false);
-
     sessionRunTime.set(_sessionRunTimer.elapsed() / MSECS_PER_SECOND);
     DependencyManager::get<AudioClient>()->saveSettings();
     DependencyManager::get<LODManager>()->saveSettings();
diff --git a/interface/src/ui/LoginDialog.cpp b/interface/src/ui/LoginDialog.cpp
index 6d94e1419b..5116c2a92c 100644
--- a/interface/src/ui/LoginDialog.cpp
+++ b/interface/src/ui/LoginDialog.cpp
@@ -43,7 +43,6 @@ LoginDialog::LoginDialog(QQuickItem *parent) : OffscreenQmlDialog(parent) {
 }
 
 LoginDialog::~LoginDialog() {
-    Settings settings;
     Setting::Handle<bool> loginDialogPoppedUp{ "loginDialogPoppedUp", false };
     auto poppedUp = loginDialogPoppedUp.get();
     if (poppedUp) {
@@ -51,7 +50,7 @@ LoginDialog::~LoginDialog() {
         data["action"] = "user opted out";
         UserActivityLogger::getInstance().logAction("encourageLoginDialog", data);
     }
-    settings.setValue("loginDialogPoppedUp", false);
+    loginDialogPoppedUp.set(false);
 }
 
 void LoginDialog::showWithSelection()