diff --git a/UndertaleModTool/MainWindow.xaml.cs b/UndertaleModTool/MainWindow.xaml.cs
index 19f1a1d93..61c5bcb2f 100644
--- a/UndertaleModTool/MainWindow.xaml.cs
+++ b/UndertaleModTool/MainWindow.xaml.cs
@@ -502,6 +502,11 @@ private async void Window_Loaded(object sender, RoutedEventArgs e)
 
             RunGMSDebuggerItem.Visibility = Settings.Instance.ShowDebuggerOption
                                             ? Visibility.Visible : Visibility.Collapsed;
+
+            if (Settings.Instance.CheckForUpdatesAtStartup)
+            {
+                _ = CheckForUpdates(isStartup: true);
+            }
         }
 
         public Dictionary<string, NamedPipeServerStream> childFiles = new Dictionary<string, NamedPipeServerStream>();
@@ -2878,7 +2883,12 @@ private void MenuItem_GitHub_Click(object sender, RoutedEventArgs e)
             OpenBrowser("https://github.com/UnderminersTeam/UndertaleModTool");
         }
 
-        private async void MenuItem_CheckForUpdates_Click(object sender, RoutedEventArgs e)
+        private void MenuItem_CheckForUpdates_Click(object sender, RoutedEventArgs e)
+        {
+            _ = CheckForUpdates();
+        }
+
+        async Task CheckForUpdates(bool isStartup = false)
         {
             LoaderDialog loaderDialog = new("Check for updates", "Checking for updates...");
             loaderDialog.Owner = this;
@@ -2901,8 +2911,11 @@ private async void MenuItem_CheckForUpdates_Click(object sender, RoutedEventArgs
 
                     if (response?.IsSuccessStatusCode != true)
                     {
-                        string errText = $"{(response is null ? "Check your internet connection." : $"HTTP error - {response.ReasonPhrase}.")}";
-                        loaderDialog.ShowError($"Failed to check for updates!\n{errText}");
+                        if (!isStartup)
+                        {
+                            string errText = $"{(response is null ? "Check your internet connection." : $"HTTP error - {response.ReasonPhrase}.")}";
+                            loaderDialog.ShowError($"Failed to check for updates!\n{errText}");
+                        }
                         return;
                     }
 
@@ -2922,6 +2935,9 @@ private async void MenuItem_CheckForUpdates_Click(object sender, RoutedEventArgs
                         $"\nCurrent version: {Version} ({currentDateTime})" +
                         $"\nLatest version: {latestVersion} ({latestDateTime})" +
                         "\n" +
+                        (isStartup ?
+                        "\nYou can disable checking for updates at startup in the settings." +
+                        "\n" : "") +
                         "\nDo you want to download the latest version?") == MessageBoxResult.Yes)
                     {
                         OpenBrowser((string)jsonResponse["html_url"]);
@@ -2932,7 +2948,10 @@ private async void MenuItem_CheckForUpdates_Click(object sender, RoutedEventArgs
                 }
                 else
                 {
-                    loaderDialog.ShowMessage("UndertaleModTool is up to date.");
+                    if (!isStartup)
+                    {
+                        loaderDialog.ShowMessage("UndertaleModTool is up to date.");
+                    }
                 }
             }
             finally
diff --git a/UndertaleModTool/Settings.cs b/UndertaleModTool/Settings.cs
index b20c8d1a9..b5aec15df 100644
--- a/UndertaleModTool/Settings.cs
+++ b/UndertaleModTool/Settings.cs
@@ -1,10 +1,6 @@
 using System;
-using System.Collections.Generic;
 using System.IO;
-using System.Linq;
-using System.Text;
 using System.Text.Json;
-using System.Threading.Tasks;
 using System.Windows;
 
 namespace UndertaleModTool
@@ -54,6 +50,8 @@ public class Settings
         public bool EnableDarkMode { get; set; } = false;
         public bool ShowDebuggerOption { get; set; } = false;
 
+        public bool CheckForUpdatesAtStartup { get; set; } = true;
+
         public static Settings Instance;
 
         public static JsonSerializerOptions JsonOptions = new JsonSerializerOptions
diff --git a/UndertaleModTool/Windows/SettingsWindow.xaml b/UndertaleModTool/Windows/SettingsWindow.xaml
index 76b2e7c5d..b7dba5fc5 100644
--- a/UndertaleModTool/Windows/SettingsWindow.xaml
+++ b/UndertaleModTool/Windows/SettingsWindow.xaml
@@ -39,62 +39,64 @@
                 <RowDefinition Height="Auto"/>
             </Grid.RowDefinitions>
 
-            <TextBlock Grid.Row="1" Grid.Column="0" Margin="3" Text="Game Maker: Studio 1.4 path" ToolTip="Required only if you want to use the Studio runner rather than the .exe or run the game under debugger."/>
-            <local:TextBoxDark Grid.Row="1" Grid.Column="1" Margin="3" Grid.ColumnSpan="3" Text="{Binding GameMakerStudioPath}"/>
+            <TextBlock Grid.Row="1" Grid.Column="0" Margin="3,3,3,3" Text="Game Maker: Studio 1.4 path" ToolTip="Required only if you want to use the Studio runner rather than the .exe or run the game under debugger."/>
+            <local:TextBoxDark Grid.Row="1" Grid.Column="1" Margin="3,3,3,3" Grid.ColumnSpan="3" Text="{Binding GameMakerStudioPath}"/>
 
-            <TextBlock Grid.Row="2" Grid.Column="0" Margin="3" Text="Game Maker: Studio 2 runtimes path" ToolTip="Required only if you want to run GMS2 games using the Studio runner rather than the .exe"/>
-            <local:TextBoxDark Grid.Row="2" Grid.Column="1" Margin="3" Grid.ColumnSpan="3" Text="{Binding GameMakerStudio2RuntimesPath}"/>
+            <TextBlock Grid.Row="2" Grid.Column="0" Margin="3,3,3,3" Text="Game Maker: Studio 2 runtimes path" ToolTip="Required only if you want to run GMS2 games using the Studio runner rather than the .exe"/>
+            <local:TextBoxDark Grid.Row="2" Grid.Column="1" Margin="3,3,3,3" Grid.ColumnSpan="3" Text="{Binding GameMakerStudio2RuntimesPath}"/>
 
-            <CheckBox Grid.Row="3" Grid.Column="0" Margin="3" Content="" IsChecked="{Binding AssetOrderSwappingEnabled}"/>
-            <TextBlock Grid.Row="3" Grid.Column="0" Margin="25 2 2 2" Text="Enable asset order swapping" ToolTip="Toggles dragging &amp; dropping assets in the asset tabs to different positions in the list. Disabled by default."/>
-            <CheckBox Grid.Row="3" Grid.Column="2" Margin="3" Content="" IsChecked="{Binding WarnOnClose}"/>
-            <TextBlock Grid.Row="3" Grid.Column="2" Margin="25 2 2 2" Text="Warn about saving before closing" ToolTip="Warn about saving before closing. Enabled by default."/>
+            <CheckBox Grid.Row="3" Grid.Column="0" Margin="3,3,3,3" Content="" IsChecked="{Binding AssetOrderSwappingEnabled}"/>
+            <TextBlock Grid.Row="3" Grid.Column="0" Margin="25,2,2,2" Text="Enable asset order swapping" ToolTip="Toggles dragging &amp; dropping assets in the asset tabs to different positions in the list. Disabled by default."/>
+            <CheckBox Grid.Row="3" Grid.Column="2" Margin="3,3,3,3" Content="" IsChecked="{Binding WarnOnClose}"/>
+            <TextBlock Grid.Row="3" Grid.Column="2" Margin="25,2,2,2" Text="Warn about saving before closing" ToolTip="Warn about saving before closing. Enabled by default."/>
 
-            <CheckBox Grid.Row="4" Grid.Column="0" Margin="3" Content="" IsChecked="{Binding AutomaticFileAssociation}"/>
-            <TextBlock Grid.Row="4" Grid.Column="0" Margin="25 2 2 2" Text="Automatically associate .win files" ToolTip="Automatic file association. Enabled by default."/>
-            <CheckBox Grid.Row="4" Grid.Column="2" Margin="3" Content="" IsChecked="{Binding TempRunMessageShow}"/>
-            <TextBlock Grid.Row="4" Grid.Column="2" Margin="25 2 2 2" Text="Warn about temp running" ToolTip="Warn about temp running. Enabled by default."/>
+            <CheckBox Grid.Row="4" Grid.Column="0" Margin="3,3,3,3" Content="" IsChecked="{Binding AutomaticFileAssociation}"/>
+            <TextBlock Grid.Row="4" Grid.Column="0" Margin="25,2,2,2" Text="Automatically associate .win files" ToolTip="Automatic file association. Enabled by default."/>
+            <CheckBox Grid.Row="4" Grid.Column="2" Margin="3,3,3,3" Content="" IsChecked="{Binding TempRunMessageShow}"/>
+            <TextBlock Grid.Row="4" Grid.Column="2" Margin="25,2,2,2" Text="Warn about temp running" ToolTip="Warn about temp running. Enabled by default."/>
 
-            <CheckBox Grid.Row="5" Grid.Column="0" Margin="3" Content="" IsChecked="{Binding UseGMLCache}"/>
-            <TextBlock Grid.Row="5" Grid.Column="0" Margin="25 2 2 2" Text="Use decompiled code cache (experimental)" ToolTip="Used by some scripts (e.g. &quot;Search.csx&quot;) for acceleration. Disabled by default."/>
-            <CheckBox Grid.Row="5" Grid.Column="2" Margin="3" Content="" IsChecked="{Binding ShowDebuggerOption}"/>
-            <TextBlock Grid.Row="5" Grid.Column="2" Margin="25 2 2 2" Text="Show &quot;Run game under GMS debugger&quot; file option" ToolTip="Whether to show the option in the &quot;File&quot; menu. Disabled by default."/>
+            <CheckBox Grid.Row="5" Grid.Column="0" Margin="3,3,3,3" Content="" IsChecked="{Binding UseGMLCache}"/>
+            <TextBlock Grid.Row="5" Grid.Column="0" Margin="25,2,2,2" Text="Use decompiled code cache (experimental)" ToolTip="Used by some scripts (e.g. &quot;Search.csx&quot;) for acceleration. Disabled by default."/>
+            <CheckBox Grid.Row="5" Grid.Column="2" Margin="3,3,3,3" Content="" IsChecked="{Binding ShowDebuggerOption}"/>
+            <TextBlock Grid.Row="5" Grid.Column="2" Margin="25,2,2,2" Text="Show &quot;Run game under GMS debugger&quot; file option" ToolTip="Whether to show the option in the &quot;File&quot; menu. Disabled by default."/>
 
-            <Separator Grid.Row="6" Grid.ColumnSpan="4" Margin="10"/>
+            <Separator Grid.Row="6" Grid.ColumnSpan="4" Margin="10,10,10,10"/>
 
-            <CheckBox Grid.Row="7" Grid.Column="0" Margin="3" Content="" IsChecked="{Binding EnableDarkMode}"/>
-            <TextBlock Grid.Row="7" Grid.Column="0" Margin="25 2 2 2" Text="Enable dark mode" ToolTip="Makes the program interface dark. Disabled by default."/>
+            <CheckBox Content="Check for updates at startup" HorizontalAlignment="Left" Margin="3,3,0,0" Grid.Row="7" VerticalAlignment="Top" Grid.RowSpan="1" Height="15" Width="170" IsChecked="{Binding CheckForUpdatesAtStartup}"/>
 
-            <Separator Grid.Row="8" Grid.ColumnSpan="4" Margin="10"/>
+            <CheckBox Grid.Row="8" Grid.Column="0" Margin="3,3,3,3" Content="" IsChecked="{Binding EnableDarkMode}"/>
+            <TextBlock Grid.Row="8" Grid.Column="0" Margin="25,2,2,2" Text="Enable dark mode" ToolTip="Makes the program interface dark. Disabled by default."/>
 
-            <CheckBox Grid.Row="9" Grid.Column="0" Margin="3" VerticalAlignment="Center" Name="gridWidthCheckbox" Content="" IsChecked="{Binding GridWidthEnabled}"/>
-            <TextBlock Grid.Row="9" Grid.Column="0" Margin="25 2 2 2" VerticalAlignment="Center" Text="Global grid width" ToolTip="This option globally overrides the automatic assignment of a room's grid width based on the most used tile's width in that room."/>
-            <local:TextBoxDark Grid.Row="9" Grid.Column="1" Margin="3" IsEnabled="{Binding ElementName=gridWidthCheckbox, Path=IsChecked}" Text="{Binding GlobalGridWidth}"/>
+            <Separator Grid.Row="9" Grid.ColumnSpan="4" Margin="10,10,10,10"/>
 
-            <CheckBox Grid.Row="10" Grid.Column="0" Margin="3" VerticalAlignment="Center" Name="gridHeightCheckbox" Content="" IsChecked="{Binding GridHeightEnabled}"/>
-            <TextBlock Grid.Row="10" Grid.Column="0" Margin="25 2 2 2"  VerticalAlignment="Center" Text="Global grid height" ToolTip="This option globally overrides the automatic assignment of a room's grid height based on the most used tile's height in that room."/>
-            <local:TextBoxDark Grid.Row="10" Grid.Column="1" Margin="3" IsEnabled="{Binding ElementName=gridHeightCheckbox, Path=IsChecked}" Text="{Binding GlobalGridHeight}"/>
+            <CheckBox Grid.Row="10" Grid.Column="0" Margin="3,0,3,0" VerticalAlignment="Center" Name="gridWidthCheckbox" Content="" IsChecked="{Binding GridWidthEnabled}" Height="15"/>
+            <TextBlock Grid.Row="10" Grid.Column="0" Margin="25,0,2,0" VerticalAlignment="Center" Text="Global grid width" ToolTip="This option globally overrides the automatic assignment of a room's grid width based on the most used tile's width in that room." Height="16"/>
+            <local:TextBoxDark Grid.Row="10" Grid.Column="1" Margin="3,3,3,3" IsEnabled="{Binding ElementName=gridWidthCheckbox, Path=IsChecked}" Text="{Binding GlobalGridWidth}"/>
 
-            <CheckBox Grid.Row="9" Grid.Column="2" Margin="3" VerticalAlignment="Center" Name="gridThicknessCheckBox" Content="" IsChecked="{Binding GridThicknessEnabled}"/>
-            <TextBlock Grid.Row="9" Grid.Column="2" Margin="25 2 2 2" VerticalAlignment="Center" Text="Global grid thickness" ToolTip="This option globally overrides the automatic assignment of a room's grid thickness."/>
-            <local:TextBoxDark Grid.Row="9" Grid.Column="3" Margin="3" IsEnabled="{Binding ElementName=gridThicknessCheckBox, Path=IsChecked}" Text="{Binding GlobalGridThickness}"/>
+            <CheckBox Grid.Row="11" Grid.Column="0" Margin="3,0,3,0" VerticalAlignment="Center" Name="gridHeightCheckbox" Content="" IsChecked="{Binding GridHeightEnabled}" Height="15"/>
+            <TextBlock Grid.Row="11" Grid.Column="0" Margin="25,0,2,0"  VerticalAlignment="Center" Text="Global grid height" ToolTip="This option globally overrides the automatic assignment of a room's grid height based on the most used tile's height in that room." Height="16"/>
+            <local:TextBoxDark Grid.Row="11" Grid.Column="1" Margin="3,3,3,3" IsEnabled="{Binding ElementName=gridHeightCheckbox, Path=IsChecked}" Text="{Binding GlobalGridHeight}"/>
 
-            <Separator Grid.Row="13" Grid.ColumnSpan="4" Margin="10"/>
+            <CheckBox Grid.Row="10" Grid.Column="2" Margin="3,0,3,0" VerticalAlignment="Center" Name="gridThicknessCheckBox" Content="" IsChecked="{Binding GridThicknessEnabled}" Height="15"/>
+            <TextBlock Grid.Row="10" Grid.Column="2" Margin="25,0,2,0" VerticalAlignment="Center" Text="Global grid thickness" ToolTip="This option globally overrides the automatic assignment of a room's grid thickness." Height="16"/>
+            <local:TextBoxDark Grid.Row="10" Grid.Column="3" Margin="3,3,3,3" IsEnabled="{Binding ElementName=gridThicknessCheckBox, Path=IsChecked}" Text="{Binding GlobalGridThickness}"/>
 
-            <TextBlock Grid.Row="14" Grid.Column="0" Grid.ColumnSpan="4" Margin="3" TextWrapping="Wrap" Foreground="Red" FontWeight="Bold" Text="Warning: the following options are currently experimental, as the profile system is a work in progress. Usage of the system is at your own risk, and though it is relatively stable, it may not be compatible in the future."/>
+            <Separator Grid.Row="12" Grid.ColumnSpan="4" Margin="10,10,10,10" Grid.RowSpan="2"/>
 
-            <CheckBox Grid.Row="15" Grid.Column="0" Margin="3" VerticalAlignment="Center" Content="" IsChecked="{Binding ProfileModeEnabled}"/>
-            <TextBlock Grid.Row="15" Grid.Column="0" Margin="25 2 2 2" VerticalAlignment="Center" Text="Enable profile mode" ToolTip="Toggles the 'decompile once and compile many' profile mode. Enabled by default. May need to be disabled for certain operations."/>
+            <TextBlock Grid.Row="14" Grid.Column="0" Grid.ColumnSpan="4" Margin="3,3,3,3" TextWrapping="Wrap" Foreground="Red" FontWeight="Bold" Text="Warning: the following options are currently experimental, as the profile system is a work in progress. Usage of the system is at your own risk, and though it is relatively stable, it may not be compatible in the future."/>
 
-            <CheckBox Grid.Row="15" Grid.Column="2" Margin="3" VerticalAlignment="Center" Content="" IsChecked="{Binding ProfileMessageShown}"/>
-            <TextBlock Grid.Row="15" Grid.Column="2" Margin="25 2 2 2" VerticalAlignment="Center" Text="Profile mode message shown" ToolTip="On first load, this will show you the profile mode loaded message. If this somehow breaks, you can manually toggle it here."/>
+            <CheckBox Grid.Row="15" Grid.Column="0" Margin="3,0,3,0" VerticalAlignment="Center" Content="" IsChecked="{Binding ProfileModeEnabled}" Height="15"/>
+            <TextBlock Grid.Row="15" Grid.Column="0" Margin="25,0,2,0" VerticalAlignment="Center" Text="Enable profile mode" ToolTip="Toggles the 'decompile once and compile many' profile mode. Enabled by default. May need to be disabled for certain operations." Height="16"/>
 
-            <CheckBox Grid.Row="17" Grid.Column="0" Margin="3" VerticalAlignment="Center" Content="" IsChecked="{Binding DeleteOldProfileOnSave}"/>
-            <TextBlock Grid.Row="17" Grid.Column="0" Margin="25 2 2 2" VerticalAlignment="Center" Text="Delete old profile on saving" ToolTip="Deletes the profile obsoleted on saving. Saves on file space at the expense of losing code information for variants. Enabled by default."/>
+            <CheckBox Grid.Row="15" Grid.Column="2" Margin="3,0,3,0" VerticalAlignment="Center" Content="" IsChecked="{Binding ProfileMessageShown}" Height="15"/>
+            <TextBlock Grid.Row="15" Grid.Column="2" Margin="25,0,2,0" VerticalAlignment="Center" Text="Profile mode message shown" ToolTip="On first load, this will show you the profile mode loaded message. If this somehow breaks, you can manually toggle it here." Height="16"/>
 
-            <Separator Grid.Row="18" Grid.ColumnSpan="4" Margin="10"/>
-            <local:ButtonDark Grid.Row="19" Grid.Column="0" Grid.ColumnSpan="1" Margin="5" Click="AppDataButton_Click">Open application data folder</local:ButtonDark>
-            <local:ButtonDark Grid.Row="19" Grid.Column="2" Grid.ColumnSpan="2" Margin="5" Click="UpdateAppButton_Click" x:Name="UpdateAppButton" HorizontalAlignment="Right" Width="223" Visibility="{Binding UpdaterButtonVisibility}">Update app to latest commit</local:ButtonDark>
+            <CheckBox Grid.Row="17" Grid.Column="0" Margin="3,0,3,0" VerticalAlignment="Center" Content="" IsChecked="{Binding DeleteOldProfileOnSave}" Height="15"/>
+            <TextBlock Grid.Row="17" Grid.Column="0" Margin="25,0,2,0" VerticalAlignment="Center" Text="Delete old profile on saving" ToolTip="Deletes the profile obsoleted on saving. Saves on file space at the expense of losing code information for variants. Enabled by default." Height="16"/>
+
+            <Separator Grid.Row="18" Grid.ColumnSpan="4" Margin="10,10,10,10"/>
+            <local:ButtonDark Grid.Row="19" Grid.Column="0" Grid.ColumnSpan="1" Margin="5,5,5,5" Click="AppDataButton_Click">Open application data folder</local:ButtonDark>
+            <local:ButtonDark Grid.Row="19" Grid.Column="2" Grid.ColumnSpan="2" Margin="184,5,0,5" Click="UpdateAppButton_Click" x:Name="UpdateAppButton" HorizontalAlignment="Left" Width="223" Visibility="{Binding UpdaterButtonVisibility}">Update app to latest commit</local:ButtonDark>
         </Grid>
     </ScrollViewer>
 </Window>
diff --git a/UndertaleModTool/Windows/SettingsWindow.xaml.cs b/UndertaleModTool/Windows/SettingsWindow.xaml.cs
index dd4cb7c1b..8fd30fdab 100644
--- a/UndertaleModTool/Windows/SettingsWindow.xaml.cs
+++ b/UndertaleModTool/Windows/SettingsWindow.xaml.cs
@@ -1,18 +1,4 @@
-using System;
-using System.Collections.Generic;
-using System.Configuration;
-using System.Diagnostics;
-using System.Linq;
-using System.Text;
-using System.Threading.Tasks;
-using System.Windows;
-using System.Windows.Controls;
-using System.Windows.Data;
-using System.Windows.Documents;
-using System.Windows.Input;
-using System.Windows.Media;
-using System.Windows.Media.Imaging;
-using System.Windows.Shapes;
+using System.Windows;
 
 namespace UndertaleModTool
 {
@@ -209,6 +195,16 @@ public static bool ShowDebuggerOption
             }
         }
 
+        public static bool CheckForUpdatesAtStartup
+        {
+            get => Settings.Instance.CheckForUpdatesAtStartup;
+            set
+            {
+                Settings.Instance.CheckForUpdatesAtStartup = value;
+                Settings.Save();
+            }
+        }
+
         public bool UpdateButtonEnabled
         {
             get => UpdateAppButton.IsEnabled;