diff --git a/chrome/content/zotero/standalone/standalone.js b/chrome/content/zotero/standalone/standalone.js
index 43b6a40383..8585db8f20 100644
--- a/chrome/content/zotero/standalone/standalone.js
+++ b/chrome/content/zotero/standalone/standalone.js
@@ -942,23 +942,26 @@ ZoteroStandalone.DebugOutput = {
 	
 	
 	restartEnabled: function () {
-		var ps = Services.prompt;
-		var buttonFlags = ps.BUTTON_POS_0 * ps.BUTTON_TITLE_IS_STRING
-				+ ps.BUTTON_POS_1 * ps.BUTTON_TITLE_CANCEL
-				+ ps.BUTTON_POS_2 * ps.BUTTON_TITLE_IS_STRING;
-		var index = ps.confirmEx(
-			null,
-			Zotero.getString('zotero.debugOutputLogging'),
-			Zotero.getString('zotero.debugOutputLogging.enabledAfterRestart', [Zotero.clientName]),
-			buttonFlags,
-			Zotero.getString('general.restartNow'),
-			null, Zotero.getString('general.restartLater'), null, {}
-		);
-		if (index != 1) {
-			Zotero.Prefs.set('debug.store', true);
-		}
+		var checkbox = { value: true };
+		var index = Zotero.Prompt.confirm({
+			title: Zotero.getString('zotero.debugOutputLogging'),
+			text: Zotero.getString('zotero.debugOutputLogging.enabledAfterRestart', [Zotero.clientName]),
+			button0: Zotero.getString('general-restartApp'),
+			button1: Services.prompt.BUTTON_TITLE_CANCEL,
+			checkLabel: Zotero.getString('debug-output-logging-restart-in-troubleshooting-mode-checkbox'),
+			checkbox,
+		});
 		if (index == 0) {
-			Zotero.Utilities.Internal.quit(true);
+			Zotero.Prefs.set('debug.store', true);
+			
+			// Restart in Troubleshooting Mode
+			if (checkbox.value) {
+				Services.startup.restartInSafeMode(Ci.nsIAppStartup.eAttemptQuit);
+			}
+			// Restart in normal mode
+			else {
+				Zotero.Utilities.Internal.quit(true);
+			}
 		}
 	},
 	
diff --git a/chrome/locale/en-US/zotero/zotero.ftl b/chrome/locale/en-US/zotero/zotero.ftl
index 08c39de8ed..3e6f2f7cff 100644
--- a/chrome/locale/en-US/zotero/zotero.ftl
+++ b/chrome/locale/en-US/zotero/zotero.ftl
@@ -39,6 +39,8 @@ general-go-back = Go Back
 general-accept = Accept
 general-cancel = Cancel
 general-show-in-library = Show in Library
+general-restartApp = Restart { -app-name }
+general-restartInTroubleshootingMode = Restart in Troubleshooting Mode
 
 citation-style-label = Citation Style:
 language-label = Language:
@@ -412,10 +414,12 @@ licenses-cc-by-nc-sa = Creative Commons Attribution-NonCommercial-ShareAlike 4.0
 licenses-cc-more-info = Be sure you have read the Creative Commons <a data-l10n-name="license-considerations">Considerations for licensors</a> before placing your work under a CC license. Note that the license you apply cannot be revoked, even if you later choose different terms or cease publishing the work.
 licenses-cc0-more-info = Be sure you have read the Creative Commons <a data-l10n-name="license-considerations">CC0 FAQ</a> before applying CC0 to your work. Please note that dedicating your work to the public domain is irreversible, even if you later choose different terms or cease publishing the work.
 
+debug-output-logging-restart-in-troubleshooting-mode-checkbox = { general-restartInTroubleshootingMode }
+
 restart-in-troubleshooting-mode-menuitem =
     .label = Restart in Troubleshooting Mode…
     .accesskey = T
-restart-in-troubleshooting-mode-dialog-title = Restart in Troubleshooting Mode
+restart-in-troubleshooting-mode-dialog-title = { general-restartInTroubleshootingMode }
 restart-in-troubleshooting-mode-dialog-description = { -app-name } will restart with all plugins disabled. Some features may not function correctly while Troubleshooting Mode is enabled.
 
 menu-ui-density =