diff --git a/web/repertory/lib/helpers.dart b/web/repertory/lib/helpers.dart
index 49a4a6e7..6d5f25c7 100644
--- a/web/repertory/lib/helpers.dart
+++ b/web/repertory/lib/helpers.dart
@@ -12,6 +12,10 @@ class NullPasswordException implements Exception {
   String error() => 'password cannot be null';
 }
 
+class AuthenticationFailedException implements Exception {
+  String error() => 'failed to authenticate user';
+}
+
 // ignore: prefer_function_declarations_over_variables
 final Validator noRestrictedChars = (value) {
   return [
@@ -231,30 +235,37 @@ bool validateSettings(
 }
 
 Future<Map<String, dynamic>> convertAllToString(
-  Map<String, dynamic> settings,
-) async {
-  final password = await promptPassword();
-  if (password == null) {
-    throw NullPasswordException();
+  Map<String, dynamic> settings, {
+  String? password,
+}) async {
+  for (var entry in settings.entries) {
+    if (entry.value is Map<String, dynamic>) {
+      convertAllToString(entry.value, password: password);
+      continue;
+    }
+
+    if (entry.key == 'ApiPassword' ||
+        entry.key == 'EncryptionToken' ||
+        entry.key == 'SecretKey') {
+      if (entry.value.isEmpty) {
+        continue;
+      }
+
+      if (password == null) {
+        password = await promptPassword();
+        if (password == null) {
+          throw NullPasswordException();
+        }
+      }
+
+      settings[entry.key] = encryptValue(entry.value, password);
+    } else if (entry.value is String) {
+      continue;
+    }
+
+    settings[entry.key] = entry.value.toString();
   }
 
-  settings.forEach((key, value) {
-    if (value is Map<String, dynamic>) {
-      convertAllToString(value);
-      return;
-    }
-
-    if (key == 'ApiPassword' ||
-        key == 'EncryptionToken' ||
-        key == 'SecretKey') {
-      value = encryptValue(value, password);
-    } else if (value is String) {
-      return;
-    }
-
-    settings[key] = value.toString();
-  });
-
   return settings;
 }
 
diff --git a/web/repertory/lib/widgets/ui_settings.dart b/web/repertory/lib/widgets/ui_settings.dart
index be6feb8f..9d06f912 100644
--- a/web/repertory/lib/widgets/ui_settings.dart
+++ b/web/repertory/lib/widgets/ui_settings.dart
@@ -3,9 +3,12 @@ import 'dart:convert' show jsonEncode;
 import 'package:collection/collection.dart';
 import 'package:flutter/material.dart';
 import 'package:http/http.dart' as http;
+import 'package:repertory/constants.dart' as constants;
 import 'package:repertory/helpers.dart'
     show
+        AuthenticationFailedException,
         convertAllToString,
+        displayErrorMessage,
         getBaseUri,
         getSettingDescription,
         getSettingValidators,
@@ -104,22 +107,36 @@ class _UISettingsWidgetState extends State<UISettingsWidget> {
       widget.settings,
       widget.origSettings,
     )) {
+      displayAuthError() {
+        if (constants.navigatorKey.currentContext != null) {
+          displayErrorMessage(
+            constants.navigatorKey.currentContext!,
+            "Authentication failed",
+          );
+        }
+      }
+
       convertAllToString(widget.settings)
           .then((map) async {
             try {
-              await http.put(
+              final response = await http.put(
                 Uri.parse(
                   Uri.encodeFull(
                     '${getBaseUri()}/api/v1/settings?data=${jsonEncode(map)}',
                   ),
                 ),
               );
+              if (response.statusCode == 500) {
+                displayAuthError();
+              }
             } catch (e) {
               debugPrint('$e');
+              displayAuthError();
             }
           })
           .catchError((e) {
             debugPrint('$e');
+            displayAuthError();
           });
     }