diff --git a/Flow.Launcher/App.xaml.cs b/Flow.Launcher/App.xaml.cs
index 4ebff16a9..8c970eddd 100644
--- a/Flow.Launcher/App.xaml.cs
+++ b/Flow.Launcher/App.xaml.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Diagnostics;
 using System.Text;
 using System.Threading.Tasks;
@@ -104,14 +104,22 @@ namespace Flow.Launcher
             });
         }
 
-
         private void AutoStartup()
         {
-            if (_settings.StartFlowLauncherOnSystemStartup)
+            // we try to enable auto-startup on first launch, or reenable if it was removed
+            // but the user still has the setting set
+            if (_settings.StartFlowLauncherOnSystemStartup && !Helper.AutoStartup.IsEnabled)
             {
-                if (!SettingWindow.StartupSet())
+                try
                 {
-                    SettingWindow.SetStartup();
+                    Helper.AutoStartup.Enable();
+                }
+                catch (Exception e)
+                {
+                    // but if it fails (permissions, etc) then don't keep retrying
+                    // this also gives the user a visual indication in the Settings widget
+                    _settings.StartFlowLauncherOnSystemStartup = false;
+                    Notification.Show(InternationalizationManager.Instance.GetTranslation("setAutoStartFailed"), e.Message);
                 }
             }
         }
diff --git a/Flow.Launcher/Helper/AutoStartup.cs b/Flow.Launcher/Helper/AutoStartup.cs
new file mode 100644
index 000000000..956324020
--- /dev/null
+++ b/Flow.Launcher/Helper/AutoStartup.cs
@@ -0,0 +1,63 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Text;
+using System.Threading.Tasks;
+using Flow.Launcher.Infrastructure;
+using Flow.Launcher.Infrastructure.Logger;
+using Microsoft.Win32;
+
+namespace Flow.Launcher.Helper
+{
+    public class AutoStartup
+    {
+        private const string StartupPath = "SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\Run";
+
+        public static bool IsEnabled
+        {
+            get
+            {
+                try
+                {
+                    using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
+                    var path = key?.GetValue(Constant.FlowLauncher) as string;
+                    return path == Constant.ExecutablePath;
+                }
+                catch (Exception e)
+                {
+                    Log.Error("AutoStartup", $"Ignoring non-critical registry error (querying if enabled): {e}");
+                }
+
+                return false;
+            }
+        }
+
+        public static void Disable()
+        {
+            try
+            {
+                using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
+                key?.DeleteValue(Constant.FlowLauncher, false);
+            }
+            catch (Exception e)
+            {
+                Log.Error("AutoStartup", $"Failed to disable auto-startup: {e}");
+                throw;
+            }
+        }
+
+        internal static void Enable()
+        {
+            try
+            {
+                using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
+                key?.SetValue(Constant.FlowLauncher, Constant.ExecutablePath);
+            }
+            catch (Exception e)
+            {
+                Log.Error("AutoStartup", $"Failed to enable auto-startup: {e}");
+                throw;
+            }
+        }
+    }
+}
diff --git a/Flow.Launcher/Languages/en.xaml b/Flow.Launcher/Languages/en.xaml
index 6ec3bb4ef..bdf745052 100644
--- a/Flow.Launcher/Languages/en.xaml
+++ b/Flow.Launcher/Languages/en.xaml
@@ -30,6 +30,7 @@
     <system:String x:Key="portableMode">Portable Mode</system:String>
     <system:String x:Key="portableModeToolTIp">Store all settings and user data in one folder (Useful when used with removable drives or cloud services).</system:String>
     <system:String x:Key="startFlowLauncherOnSystemStartup">Start Flow Launcher on system startup</system:String>
+    <system:String x:Key="setAutoStartFailed">Error setting launch on startup</system:String>
     <system:String x:Key="hideFlowLauncherWhenLoseFocus">Hide Flow Launcher when focus is lost</system:String>
     <system:String x:Key="dontPromptUpdateMsg">Do not show new version notifications</system:String>
     <system:String x:Key="rememberLastLocation">Remember last launch location</system:String>
diff --git a/Flow.Launcher/Notification.cs b/Flow.Launcher/Notification.cs
index 3f5565eeb..57c1e88f2 100644
--- a/Flow.Launcher/Notification.cs
+++ b/Flow.Launcher/Notification.cs
@@ -18,7 +18,7 @@ namespace Flow.Launcher
         }
 
         [System.Diagnostics.CodeAnalysis.SuppressMessage("Interoperability", "CA1416:Validate platform compatibility", Justification = "<Pending>")]
-        public static void Show(string title, string subTitle, string iconPath)
+        public static void Show(string title, string subTitle, string iconPath = null)
         {
             // Handle notification for win7/8/early win10
             if (legacy)
@@ -45,4 +45,4 @@ namespace Flow.Launcher
             msg.Show(title, subTitle, iconPath);
         }
     }
-}
\ No newline at end of file
+}
diff --git a/Flow.Launcher/PublicAPIInstance.cs b/Flow.Launcher/PublicAPIInstance.cs
index 81f7a2389..e698ae597 100644
--- a/Flow.Launcher/PublicAPIInstance.cs
+++ b/Flow.Launcher/PublicAPIInstance.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Linq;
 using System.Net;
@@ -286,4 +286,4 @@ namespace Flow.Launcher
 
         #endregion
     }
-}
\ No newline at end of file
+}
diff --git a/Flow.Launcher/SettingWindow.xaml b/Flow.Launcher/SettingWindow.xaml
index 73074abd3..06c9549e2 100644
--- a/Flow.Launcher/SettingWindow.xaml
+++ b/Flow.Launcher/SettingWindow.xaml
@@ -598,10 +598,8 @@
                                         <TextBlock Style="{DynamicResource SettingTitleLabel}" Text="{DynamicResource startFlowLauncherOnSystemStartup}" />
                                     </StackPanel>
                                     <CheckBox
-                                        Checked="OnAutoStartupChecked"
-                                        IsChecked="{Binding Settings.StartFlowLauncherOnSystemStartup}"
-                                        Style="{DynamicResource SideControlCheckBox}"
-                                        Unchecked="OnAutoStartupUncheck" />
+                                        IsChecked="{Binding StartFlowLauncherOnSystemStartup}"
+                                        Style="{DynamicResource SideControlCheckBox}" />
                                     <TextBlock Style="{StaticResource Glyph}">
                                         &#xe8fc;
                                     </TextBlock>
diff --git a/Flow.Launcher/SettingWindow.xaml.cs b/Flow.Launcher/SettingWindow.xaml.cs
index 120131830..c7b4baf2e 100644
--- a/Flow.Launcher/SettingWindow.xaml.cs
+++ b/Flow.Launcher/SettingWindow.xaml.cs
@@ -1,9 +1,10 @@
-using Flow.Launcher.Core.ExternalPlugins;
+using Flow.Launcher.Core.ExternalPlugins;
 using Flow.Launcher.Core.Plugin;
 using Flow.Launcher.Core.Resource;
 using Flow.Launcher.Helper;
 using Flow.Launcher.Infrastructure;
 using Flow.Launcher.Infrastructure.Hotkey;
+using Flow.Launcher.Infrastructure.Logger;
 using Flow.Launcher.Infrastructure.UserSettings;
 using Flow.Launcher.Plugin;
 using Flow.Launcher.Plugin.SharedCommands;
@@ -30,8 +31,6 @@ namespace Flow.Launcher
 {
     public partial class SettingWindow
     {
-        private const string StartupPath = "SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\Run";
-
         public readonly IPublicAPI API;
         private Settings settings;
         private SettingWindowViewModel viewModel;
@@ -58,39 +57,6 @@ namespace Flow.Launcher
             hwndTarget.RenderMode = RenderMode.SoftwareOnly;
         }
 
-        private void OnAutoStartupChecked(object sender, RoutedEventArgs e)
-        {
-            SetStartup();
-        }
-
-        private void OnAutoStartupUncheck(object sender, RoutedEventArgs e)
-        {
-            RemoveStartup();
-        }
-
-        public static void SetStartup()
-        {
-            using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
-            key?.SetValue(Constant.FlowLauncher, Constant.ExecutablePath);
-        }
-
-        private void RemoveStartup()
-        {
-            using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
-            key?.DeleteValue(Constant.FlowLauncher, false);
-        }
-
-        public static bool StartupSet()
-        {
-            using var key = Registry.CurrentUser.OpenSubKey(StartupPath, true);
-            var path = key?.GetValue(Constant.FlowLauncher) as string;
-            if (path != null)
-            {
-                return path == Constant.ExecutablePath;
-            }
-            return false;
-        }
-
         private void OnSelectPythonDirectoryClick(object sender, RoutedEventArgs e)
         {
             var dlg = new FolderBrowserDialog
@@ -384,4 +350,4 @@ namespace Flow.Launcher
             Plugins.ScrollIntoView(Plugins.SelectedItem);
         }
     }
-}
\ No newline at end of file
+}
diff --git a/Flow.Launcher/ViewModel/MainViewModel.cs b/Flow.Launcher/ViewModel/MainViewModel.cs
index fbcea504e..ab0e67519 100644
--- a/Flow.Launcher/ViewModel/MainViewModel.cs
+++ b/Flow.Launcher/ViewModel/MainViewModel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Linq;
 using System.Threading;
@@ -306,8 +306,8 @@ namespace Flow.Launcher.ViewModel
                         {
                             Notification.Show(
                                 InternationalizationManager.Instance.GetTranslation("success"),
-                                InternationalizationManager.Instance.GetTranslation("completedSuccessfully"),
-                                "");
+                                InternationalizationManager.Instance.GetTranslation("completedSuccessfully")
+                                );
                         }))
                     .ConfigureAwait(false);
             });
@@ -927,4 +927,4 @@ namespace Flow.Launcher.ViewModel
 
         #endregion
     }
-}
\ No newline at end of file
+}
diff --git a/Flow.Launcher/ViewModel/SettingWindowViewModel.cs b/Flow.Launcher/ViewModel/SettingWindowViewModel.cs
index 2fc6934d5..a63e54f3b 100644
--- a/Flow.Launcher/ViewModel/SettingWindowViewModel.cs
+++ b/Flow.Launcher/ViewModel/SettingWindowViewModel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
@@ -60,7 +60,30 @@ namespace Flow.Launcher.ViewModel
                 Settings.AutoUpdates = value;
 
                 if (value)
+                {
                     UpdateApp();
+                }
+            }
+        }
+
+        public bool StartFlowLauncherOnSystemStartup
+        {
+            get => Settings.StartFlowLauncherOnSystemStartup;
+            set
+            {
+                Settings.StartFlowLauncherOnSystemStartup = value;
+
+                try
+                {
+                    if (value)
+                        AutoStartup.Enable();
+                    else
+                        AutoStartup.Disable();
+                }
+                catch (Exception e)
+                {
+                    Notification.Show(InternationalizationManager.Instance.GetTranslation("setAutoStartFailed"), e.Message);
+                }
             }
         }