diff --git a/FreeTubeSyncer/App.axaml.cs b/FreeTubeSyncer/App.axaml.cs
index 0026e01..cf3a496 100644
--- a/FreeTubeSyncer/App.axaml.cs
+++ b/FreeTubeSyncer/App.axaml.cs
@@ -98,6 +98,7 @@ public partial class App : Application
         _settings.SyncProfile = @new.SyncProfile;
         _settings.SyncSearchHistory = @new.SyncSearchHistory;
         _settings.SyncSettings = @new.SyncSettings;
+        _settings.SettingsDirty = false;
     }
 
     public void SaveSettings()
@@ -110,6 +111,7 @@ public partial class App : Application
                 Directory.CreateDirectory(dir);
         }
         File.WriteAllText(path, JsonSerializer.Serialize(_settings));
+        _settings!.SettingsDirty = false;
         SettingsChanged?.Invoke(this, EventArgs.Empty);
     }
 
@@ -131,15 +133,23 @@ public partial class App : Application
 
     private async Task SyncMonitor()
     {
+        // TODO: Replace with Logger
+        Console.WriteLine("Sync Monitor Starting Up.");
+        // TODO: Replace with Logger
+        Console.WriteLine("Starting API Validation Check.");
         while (_isRunning)
         {
             await _semaphoreSlim.WaitAsync();
+            
             if (!await _syncers![0].PingApi())
             {
                 _semaphoreSlim.Release();
                 await Task.Delay(5000);
                 continue;
             }
+            
+            // TODO: Replace with Logger
+            Console.WriteLine("Fetching initial data from Database.");
             foreach (var syncer in _syncers!)
             {
                 await syncer.FetchDatabase();
@@ -149,6 +159,8 @@ public partial class App : Application
             break;
         }
         
+        // TODO: Replace with Logger
+        Console.WriteLine("Starting Filesystem Sync Monitoring.");
         var lastCheck = DateTime.Now;
         while (_isRunning)
         {
@@ -188,6 +200,9 @@ public partial class App : Application
             // TODO: Replace with Logger
             Console.WriteLine($"Sync completed in {syncEnd}.");
         }
+        
+        // TODO: Replace with Logger
+        Console.WriteLine($"Filesystem Sync Monitor Shutdown.");
     }
 
     private async void HandleSettingsChanged(object? sender, EventArgs e)
@@ -218,6 +233,7 @@ public partial class App : Application
             {
                 DataContext = _settings
             };
+            _settings!.SettingsDirty = false;
         }
         StampSettings();
         desktop.MainWindow!.Show();
diff --git a/FreeTubeSyncer/MainWindow.axaml b/FreeTubeSyncer/MainWindow.axaml
index d98322d..9377531 100644
--- a/FreeTubeSyncer/MainWindow.axaml
+++ b/FreeTubeSyncer/MainWindow.axaml
@@ -28,11 +28,11 @@
         <Grid
             ColumnDefinitions="170,*"
             RowDefinitions="*,*,*">
-            <ToggleSwitch Grid.Row="0" Grid.Column="0" IsPressed="{Binding SyncHistory, Mode=TwoWay}" OnContent="Sync History" />
-            <ToggleSwitch Grid.Row="0" Grid.Column="1" IsPressed="{Binding SyncPlaylist, Mode=TwoWay}" OnContent="Sync Playlists"/>
-            <ToggleSwitch Grid.Row="1" Grid.Column="0" IsPressed="{Binding SyncProfile, Mode=TwoWay}" OnContent="Sync Profiles"/>
-            <ToggleSwitch Grid.Row="1" Grid.Column="1" IsPressed="{Binding SyncSearchHistory, Mode=TwoWay}" OnContent="Sync Search History"/>
-            <ToggleSwitch Grid.Row="2" Grid.Column="0" IsPressed="{Binding SyncSettings, Mode=TwoWay}"  OnContent="Sync Settings"/>
+            <ToggleSwitch Grid.Row="0" Grid.Column="0" IsChecked="{Binding SyncHistory, Mode=TwoWay}" OnContent="Sync History" />
+            <ToggleSwitch Grid.Row="0" Grid.Column="1" IsChecked="{Binding SyncPlaylist, Mode=TwoWay}" OnContent="Sync Playlists"/>
+            <ToggleSwitch Grid.Row="1" Grid.Column="0" IsChecked="{Binding SyncProfile, Mode=TwoWay}" OnContent="Sync Profiles"/>
+            <ToggleSwitch Grid.Row="1" Grid.Column="1" IsChecked="{Binding SyncSearchHistory, Mode=TwoWay}" OnContent="Sync Search History"/>
+            <ToggleSwitch Grid.Row="2" Grid.Column="0" IsChecked="{Binding SyncSettings, Mode=TwoWay}"  OnContent="Sync Settings"/>
         </Grid>
         
         <StackPanel Orientation="Horizontal" HorizontalAlignment="Right" Spacing="10">
diff --git a/FreeTubeSyncer/REST/Syncer.cs b/FreeTubeSyncer/REST/Syncer.cs
index cf1360f..49b7ea3 100644
--- a/FreeTubeSyncer/REST/Syncer.cs
+++ b/FreeTubeSyncer/REST/Syncer.cs
@@ -67,17 +67,27 @@ public class Syncer<T> : ISyncer where T : class, IDataModel, new()
 
     public async Task<bool> PingApi()
     {
+        // TODO: Replace with Logger
+        Console.WriteLine($"Pinging API at {_client.BuildUri(new RestRequest("/ping"))}...");
         try
         {
             var res = await _client.ExecuteHeadAsync(new RestRequest("/ping"));
             if (res.StatusCode == HttpStatusCode.NotFound)
+            {
+                // TODO: Replace with Logger
+                Console.WriteLine($"Ping response 404 Not Found, Server Online!");
                 return true;
+            }
         }
         catch (Exception ex)
         {
+            // TODO: Replace with Logger
+            Console.WriteLine($"Network Error: {ex.Message}, API not alive.");
             return false;
         }
 
+        // TODO: Replace with Logger
+        Console.WriteLine("Responded with something other then 404, API not what we expected.");
         return false;
     }
 
@@ -104,6 +114,7 @@ public class Syncer<T> : ISyncer where T : class, IDataModel, new()
             if (_entries.Any(x => x.EqualId(item.Id())))
                 _entries.RemoveAll(x => x.EqualId(item.Id()));
             _entries.Add(item);
+            // TODO: Replace with Logger
             Console.WriteLine($"Posting {item.Id()}");
             await _client.PostJsonAsync<T>(_restEndpoint, item);
         }
@@ -122,11 +133,16 @@ public class Syncer<T> : ISyncer where T : class, IDataModel, new()
                 
                 if (data.Equals(entry)) continue;
                 
+                // TODO: Replace with Logger
                 Console.WriteLine($"Updated Entry for {_dbName} - {entry.Id()}");
                 _entries.RemoveAll(x => x.EqualId(entry.Id()));
             }
             else
+            {
+                // TODO: Replace with Logger
                 Console.WriteLine($"New Entry for {_dbName} - {entry.Id()}");
+            }
+
             _entries.Add(entry);
             _isDirty = true;
         }
@@ -174,6 +190,7 @@ public class Syncer<T> : ISyncer where T : class, IDataModel, new()
         if (!_isDirty)
             return;
         _syncing = true;
+        // TODO: Replace with Logger
         Console.WriteLine($"Syncing {_dbPath}...");
         var json = new List<string>();
         foreach (var entry in _entries)
@@ -187,6 +204,7 @@ public class Syncer<T> : ISyncer where T : class, IDataModel, new()
             fh.Close();
         }
         _watcher.Locked = false;
+        // TODO: Replace with Logger
         Console.WriteLine($"Updated {_dbPath}.");
         _isDirty = false;
         _syncing = false;