diff --git a/Greenshot/Forms/MainForm.cs b/Greenshot/Forms/MainForm.cs
index 3249482d6..224d0fb49 100644
--- a/Greenshot/Forms/MainForm.cs
+++ b/Greenshot/Forms/MainForm.cs
@@ -388,7 +388,8 @@ namespace Greenshot {
 			}
 			SoundHelper.Initialize();
 
-			MainForm.ResetImageScalingSize();
+			coreConfiguration.PropertyChanged += OnIconSizeChanged;
+			OnIconSizeChanged(this, new PropertyChangedEventArgs("IconSize"));
 
 			// Set the Greenshot icon visibility depending on the configuration. (Added for feature #3521446)
 			// Setting it to true this late prevents Problems with the context menu
@@ -552,12 +553,14 @@ namespace Greenshot {
 		}
 
 		/// <summary>
-		/// Reset ImageScalingSize
+		/// Fix icon reference
 		/// </summary>
-		/// <returns>Used for fixing scaling issues</returns>
-		public static void ResetImageScalingSize() {
-			MainForm thisForm = MainForm.Instance;
-			thisForm.contextMenu.ImageScalingSize = coreConfiguration.IconSize;
+		/// <param name="sender"></param>
+		/// <param name="e"></param>
+		private void OnIconSizeChanged(object sender, PropertyChangedEventArgs e) {
+			if (e.PropertyName == "IconSize") {
+				contextMenu.ImageScalingSize = coreConfiguration.IconSize;
+			}
 		}
 
 		/// <summary>
diff --git a/Greenshot/Forms/SettingsForm.cs b/Greenshot/Forms/SettingsForm.cs
index cbbb61b8a..c823bb143 100644
--- a/Greenshot/Forms/SettingsForm.cs
+++ b/Greenshot/Forms/SettingsForm.cs
@@ -368,7 +368,6 @@ namespace Greenshot {
 			
 			numericUpDown_daysbetweencheck.Value = coreConfiguration.UpdateCheckInterval;
 			numericUpDown_daysbetweencheck.Enabled = !coreConfiguration.Values["UpdateCheckInterval"].IsFixed;
-			coreConfiguration.FixIconSize();
 			numericUpdownIconSize.Value = (coreConfiguration.IconSize.Width /16) * 16;
 			CheckDestinationSettings();
 		}
@@ -417,12 +416,6 @@ namespace Greenshot {
 			Size previousValue = coreConfiguration.IconSize;
 			coreConfiguration.IconSize = new Size((int)numericUpdownIconSize.Value, (int)numericUpdownIconSize.Value);
 
-			// Clear caches when changing the settings
-			if (previousValue != coreConfiguration.IconSize) {
-				PluginUtils.ClearExeIconCache();
-				MainForm.ResetImageScalingSize();
-			}
-			coreConfiguration.FixIconSize();
 			try {
 				if (checkbox_autostartshortcut.Checked) {
 					// It's checked, so we set the RunUser if the RunAll isn't set.
diff --git a/GreenshotExternalCommandPlugin/ExternalCommandPlugin.cs b/GreenshotExternalCommandPlugin/ExternalCommandPlugin.cs
index fd692ca33..74e5bcdf4 100644
--- a/GreenshotExternalCommandPlugin/ExternalCommandPlugin.cs
+++ b/GreenshotExternalCommandPlugin/ExternalCommandPlugin.cs
@@ -24,6 +24,7 @@ using Greenshot.Plugin;
 using GreenshotPlugin.Core;
 using System;
 using System.Collections.Generic;
+using System.ComponentModel;
 using System.IO;
 using System.Windows.Forms;
 
@@ -33,6 +34,7 @@ namespace ExternalCommand {
 	/// </summary>
 	public class ExternalCommandPlugin : IGreenshotPlugin {
 		private static readonly log4net.ILog LOG = log4net.LogManager.GetLogger(typeof(ExternalCommandPlugin));
+		private static CoreConfiguration coreConfig = IniConfig.GetIniSection<CoreConfiguration>();
 		private static ExternalCommandConfiguration config = IniConfig.GetIniSection<ExternalCommandConfiguration>();
 		private IGreenshotHost host;
 		private PluginAttribute myAttributes;
@@ -121,24 +123,36 @@ namespace ExternalCommand {
 
 
 			itemPlugInRoot = new ToolStripMenuItem();
-			itemPlugInRoot.Text = Language.GetString("externalcommand", "contextmenu_configure");
 			itemPlugInRoot.Tag = host;
-			try {
-				string exePath = PluginUtils.GetExePath("cmd.exe");
-				if (exePath != null && File.Exists(exePath)) {
-					itemPlugInRoot.Image = PluginUtils.GetCachedExeIcon(exePath, 0);
-				}
-			} catch (Exception ex) {
-				LOG.Warn("Couldn't get the cmd.exe image", ex);
-			}
+			OnIconSizeChanged(this, new PropertyChangedEventArgs("IconSize"));
+			OnLanguageChanged(this, null);
 			itemPlugInRoot.Click += new System.EventHandler(ConfigMenuClick);
 
 			PluginUtils.AddToContextMenu(host, itemPlugInRoot);
-			Language.LanguageChanged += new LanguageChangedHandler(OnLanguageChanged);
+			Language.LanguageChanged += OnLanguageChanged;
+			coreConfig.PropertyChanged += OnIconSizeChanged;
 			return true;
 		}
 
-		public void OnLanguageChanged(object sender, EventArgs e) {
+		/// <summary>
+		/// Fix icon reference
+		/// </summary>
+		/// <param name="sender"></param>
+		/// <param name="e"></param>
+		private void OnIconSizeChanged(object sender, PropertyChangedEventArgs e) {
+			if (e.PropertyName == "IconSize") {
+				try {
+					string exePath = PluginUtils.GetExePath("cmd.exe");
+					if (exePath != null && File.Exists(exePath)) {
+						itemPlugInRoot.Image = PluginUtils.GetCachedExeIcon(exePath, 0);
+					}
+				} catch (Exception ex) {
+					LOG.Warn("Couldn't get the cmd.exe image", ex);
+				}
+			}
+		}
+
+		private void OnLanguageChanged(object sender, EventArgs e) {
 			if (itemPlugInRoot != null) {
 				itemPlugInRoot.Text = Language.GetString("externalcommand", "contextmenu_configure");
 			}
diff --git a/GreenshotPlugin/Core/CoreConfiguration.cs b/GreenshotPlugin/Core/CoreConfiguration.cs
index c5e911712..8a11d5837 100644
--- a/GreenshotPlugin/Core/CoreConfiguration.cs
+++ b/GreenshotPlugin/Core/CoreConfiguration.cs
@@ -18,14 +18,16 @@
  * You should have received a copy of the GNU General Public License
  * along with this program.  If not, see <http://www.gnu.org/licenses/>.
  */
-using System;
-using System.Collections.Generic;
-using System.Drawing;
-using System.IO;
-using System.Windows.Forms;
+
 using Greenshot.IniFile;
 using Greenshot.Plugin;
+using System;
+using System.Collections.Generic;
+using System.ComponentModel;
+using System.Drawing;
+using System.IO;
 using System.Reflection;
+using System.Windows.Forms;
 
 namespace GreenshotPlugin.Core {
 	public enum ClipboardFormat {
@@ -56,7 +58,9 @@ namespace GreenshotPlugin.Core {
 	/// Description of CoreConfiguration.
 	/// </summary>
 	[IniSection("Core", Description="Greenshot core configuration")]
-	public class CoreConfiguration : IniSection {
+	public class CoreConfiguration : IniSection, INotifyPropertyChanged {
+		public event PropertyChangedEventHandler PropertyChanged;
+
 		[IniProperty("Language", Description = "The language in IETF format (e.g. en-US)")]
 		public string Language;
 
@@ -256,8 +260,36 @@ namespace GreenshotPlugin.Core {
 		[IniProperty("LastCapturedRegion", Description = "The last used region, for reuse in the capture last region")]
 		public Rectangle LastCapturedRegion;
 
+		private Size _iconSize;
 		[IniProperty("IconSize", Description = "Defines the size of the icons (e.g. for the buttons in the editor), default value 16,16 anything bigger will cause scaling", DefaultValue = "16,16")]
-		public Size IconSize;
+		public Size IconSize {
+			get {
+				return _iconSize;
+			}
+			set {
+				Size newSize = value;
+				if (newSize != Size.Empty) {
+					if (newSize.Width < 16) {
+						newSize.Width = 16;
+					} else if (newSize.Width > 256) {
+						newSize.Width = 256;
+					}
+					newSize.Width = (newSize.Width / 16) * 16;
+					if (newSize.Height < 16) {
+						newSize.Height = 16;
+					} else if (IconSize.Height > 256) {
+						newSize.Height = 256;
+					}
+					newSize.Height = (newSize.Height / 16) * 16;
+				}
+				if (_iconSize != newSize) {
+					_iconSize = value;
+					if (PropertyChanged != null) {
+						PropertyChanged(this, new PropertyChangedEventArgs("IconSize"));
+					}
+				}
+			}
+		}
 
 		// Specifies what THIS build is
 		public BuildStates BuildState = BuildStates.RELEASE_CANDIDATE;
@@ -441,32 +473,7 @@ namespace GreenshotPlugin.Core {
 			if (OutputFileReduceColorsTo > 256) {
 				OutputFileReduceColorsTo = 256;
 			}
-			FixIconSize();
 		}
 
-		/// <summary>
-		/// Validation & correction of the icon size
-		/// </summary>
-		public void FixIconSize() {
-			if (IconSize == Size.Empty) {
-				IconSize = new Size(16, 16);
-			} else {
-				if (IconSize.Width < 16) {
-					IconSize.Width = 16;
-				}
-				if (IconSize.Width > 256) {
-					IconSize.Width = 256;
-				}
-				IconSize.Width = (IconSize.Width / 16) * 16;
-				if (IconSize.Height < 16) {
-					IconSize.Height = 16;
-				}
-				if (IconSize.Height > 256) {
-					IconSize.Height = 256;
-				}
-				IconSize.Height = (IconSize.Height/16)*16;
-			}
-
-		}
 	}
 }
\ No newline at end of file
diff --git a/GreenshotPlugin/Core/PluginUtils.cs b/GreenshotPlugin/Core/PluginUtils.cs
index 3eefcf11b..63467f59f 100644
--- a/GreenshotPlugin/Core/PluginUtils.cs
+++ b/GreenshotPlugin/Core/PluginUtils.cs
@@ -26,6 +26,7 @@ using log4net;
 using Microsoft.Win32;
 using System;
 using System.Collections.Generic;
+using System.ComponentModel;
 using System.Drawing;
 using System.IO;
 using System.Windows.Forms;
@@ -40,6 +41,10 @@ namespace GreenshotPlugin.Core {
 		private const string PATH_KEY = @"SOFTWARE\Microsoft\Windows\CurrentVersion\App Paths\";
 		private static IDictionary<string, Image> exeIconCache = new Dictionary<string, Image>();
 
+		static PluginUtils() {
+			conf.PropertyChanged += OnIconSizeChanged;
+		}
+
 		/// <summary>
 		/// Simple global property to get the Greenshot host
 		/// </summary>
@@ -48,18 +53,26 @@ namespace GreenshotPlugin.Core {
 			set;
 		}
 
-		public static void ClearExeIconCache() {
-			List<Image> cachedImages = new List<Image>();
-			lock (exeIconCache) {
-				foreach (string key in exeIconCache.Keys) {
-					cachedImages.Add(exeIconCache[key]);
+		/// <summary>
+		/// Clear icon cache
+		/// </summary>
+		/// <param name="sender"></param>
+		/// <param name="e"></param>
+		private static void OnIconSizeChanged(object sender, PropertyChangedEventArgs e) {
+			if (e.PropertyName == "IconSize") {
+				List<Image> cachedImages = new List<Image>();
+				lock (exeIconCache) {
+					foreach (string key in exeIconCache.Keys) {
+						cachedImages.Add(exeIconCache[key]);
+					}
+					exeIconCache.Clear();
 				}
-				exeIconCache.Clear();
-			}
-			foreach (Image cachedImage in cachedImages) {
-				if (cachedImage != null) {
-					cachedImage.Dispose();
+				foreach (Image cachedImage in cachedImages) {
+					if (cachedImage != null) {
+						cachedImage.Dispose();
+					}
 				}
+
 			}
 		}