diff --git a/Greenshot/Drawing/DrawableContainer.cs b/Greenshot/Drawing/DrawableContainer.cs
index f29bdbb5a..32d5bb923 100644
--- a/Greenshot/Drawing/DrawableContainer.cs
+++ b/Greenshot/Drawing/DrawableContainer.cs
@@ -692,10 +692,16 @@ namespace Greenshot.Drawing {
 			Invalidate();
 		}
 
-		public virtual bool CanRotate {
-			get {
-				return true;
-			}
+		/// <summary>
+		/// Retrieve the rotation angle from the matrix
+		/// </summary>
+		/// <param name="matrix"></param>
+		/// <returns></returns>
+		public static int CalculateAngle(Matrix matrix) {
+			const int M11 = 0;
+			const int M21 = 2;
+			var radians = Math.Atan2(matrix.Elements[M21], matrix.Elements[M11]);
+			return (int)-Math.Round(radians * 180 / Math.PI);
 		}
 
 		/// <summary>
diff --git a/Greenshot/Drawing/FreehandContainer.cs b/Greenshot/Drawing/FreehandContainer.cs
index 4f3984128..72a9b8369 100644
--- a/Greenshot/Drawing/FreehandContainer.cs
+++ b/Greenshot/Drawing/FreehandContainer.cs
@@ -171,15 +171,6 @@ namespace Greenshot.Drawing {
 			myBounds = Rectangle.Round(freehandPath.GetBounds());
 		}
 
-		/// <summary>
-		/// Currently we can't rotate the freehand
-		/// </summary>
-		public override bool CanRotate {
-			get {
-				return false;
-			}
-		}
-
 		/// <summary>
 		/// Do the drawing of the freehand "stroke"
 		/// </summary>
@@ -267,6 +258,10 @@ namespace Greenshot.Drawing {
 			return freehandPath.GetHashCode();
 		}
 
+		/// <summary>
+		/// This is overriden to prevent the grippers to be modified.
+		/// Might not be the best way...
+		/// </summary>
 		protected override void DoLayout() {
 		}
 
diff --git a/Greenshot/Drawing/ImageContainer.cs b/Greenshot/Drawing/ImageContainer.cs
index 55533b9ad..4bb992808 100644
--- a/Greenshot/Drawing/ImageContainer.cs
+++ b/Greenshot/Drawing/ImageContainer.cs
@@ -93,7 +93,8 @@ namespace Greenshot.Drawing {
 		public Image Image {
 			set {
 				// Remove all current bitmaps
-				DisposeImages();
+				DisposeImage();
+				DisposeShadow();
 				image = ImageHelper.Clone(value);
 				bool shadow = GetFieldValueAsBool(FieldType.SHADOW);
 				CheckShadow(shadow);
@@ -118,24 +119,42 @@ namespace Greenshot.Drawing {
 		/// <param name="disposing"></param>
 		protected override void Dispose(bool disposing) {
 			if (disposing) {
-				DisposeImages();
+				DisposeImage();
+				DisposeShadow();
 			}
-			image = null;
-			_shadowBitmap = null;
 			base.Dispose(disposing);
 		}
 
-		private void DisposeImages() {
+		private void DisposeImage() {
 			if (image != null) {
 				image.Dispose();
 			}
+			image = null;
+		}
+		private void DisposeShadow() {
 			if (_shadowBitmap != null) {
 				_shadowBitmap.Dispose();
 			}
-			image = null;
 			_shadowBitmap = null;
 		}
 
+
+
+		/// <summary>
+		/// Make sure the content is also transformed.
+		/// </summary>
+		/// <param name="matrix"></param>
+		public override void Transform(Matrix matrix) {
+			base.Transform(matrix);
+			LOG.DebugFormat("Rotating element with {0} degrees.", CalculateAngle(matrix));
+			DisposeShadow();
+			using (var tmpMatrix = new Matrix()) {
+				using (image) {
+					image = ImageHelper.ApplyEffect(image, new RotateEffect(CalculateAngle(matrix)), tmpMatrix);
+				}
+			}
+		}
+
 		/// <summary>
 		/// 
 		/// </summary>
@@ -157,7 +176,9 @@ namespace Greenshot.Drawing {
 		/// <param name="shadow"></param>
 		private void CheckShadow(bool shadow) {
 			if (shadow && _shadowBitmap == null) {
-				_shadowBitmap = ImageHelper.ApplyEffect(image, new DropShadowEffect(), new Matrix());
+				using (var matrix = new Matrix()) {
+					_shadowBitmap = ImageHelper.ApplyEffect(image, new DropShadowEffect(), matrix);
+				}
 			}
 		}