diff --git a/Greenshot/Drawing/BitmapContainer.cs b/Greenshot/Drawing/BitmapContainer.cs
index 40ac7bc02..fd4cb496c 100644
--- a/Greenshot/Drawing/BitmapContainer.cs
+++ b/Greenshot/Drawing/BitmapContainer.cs
@@ -100,7 +100,16 @@ namespace Greenshot.Drawing {
 				LOG.Debug("Loaded file: " + filename + " with resolution: " + Height + "," + Width);
 			}
 		}
-		
+
+		public override void Rotate(RotateFlipType rotateFlipType) {
+			Bitmap newBitmap = ImageHelper.RotateFlip((Bitmap)bitmap, rotateFlipType);
+			if (bitmap != null) {
+				bitmap.Dispose();
+			}
+			bitmap = newBitmap;
+			base.Rotate(rotateFlipType);
+		}
+
 		public override void Draw(Graphics graphics, RenderMode rm) {
 			if (bitmap != null) {
 				bool shadow = GetFieldValueAsBool(FieldType.SHADOW);
diff --git a/Greenshot/Drawing/DrawableContainer.cs b/Greenshot/Drawing/DrawableContainer.cs
index 57cbf8ce1..02cb111b2 100644
--- a/Greenshot/Drawing/DrawableContainer.cs
+++ b/Greenshot/Drawing/DrawableContainer.cs
@@ -590,7 +590,50 @@ namespace Greenshot.Drawing {
 			}
 			Invalidate();
 		}
-		
+
+		public virtual void Rotate(RotateFlipType rotateFlipType) {
+			// somehow the rotation is the wrong way?
+			int angle = 90;
+			if (RotateFlipType.Rotate90FlipNone == rotateFlipType) {
+				angle = 270;
+			}
+			int ox = 0;
+			int oy = 0;
+			int centerX = parent.Width >> 1;
+			int centerY = parent.Height >> 1;
+			// Transform from screen to normal coordinates
+			int px = Left - centerX;
+			int py = centerY - Top;
+			double theta = Math.PI * angle / 180.0;
+			double x1 = Math.Cos(theta) * (px - ox) - Math.Sin(theta) * (py - oy) + ox;
+			double y1 = Math.Sin(theta) * (px - ox) + Math.Cos(theta) * (py - oy) + oy;
+
+			// Transform from screen to normal coordinates
+			px = (Left + Width) - centerX;
+			py = centerY - (Top + Height);
+
+			double x2 = Math.Cos(theta) * (px - ox) - Math.Sin(theta) * (py - oy) + ox;
+			double y2 = Math.Sin(theta) * (px - ox) + Math.Cos(theta) * (py - oy) + oy;
+
+			// Transform back to screen coordinates, as we rotate the bitmap we need to switch the center X&Y
+			x1 += centerY;
+			y1 = centerX - y1;
+			x2 += centerY;
+			y2 = centerX - y2;
+
+			// Calculate to rectangle
+			double newWidth = x2 - x1;
+			double newHeight = y2 - y1;
+
+			RectangleF newRectangle = new RectangleF(
+				(float)x1,
+				(float)y1,
+				(float)newWidth,
+				(float)newHeight
+			);
+			ApplyBounds(newRectangle);
+		}
+
 		protected virtual ScaleHelper.IDoubleProcessor GetAngleRoundProcessor() {
 			return ScaleHelper.ShapeAngleRoundBehavior.Instance;
 		}
diff --git a/Greenshot/Drawing/Surface.cs b/Greenshot/Drawing/Surface.cs
index e3ba91116..43e80d4f8 100644
--- a/Greenshot/Drawing/Surface.cs
+++ b/Greenshot/Drawing/Surface.cs
@@ -572,44 +572,16 @@ namespace Greenshot.Drawing {
 						newImage = ImageHelper.CreateGrayscale((Bitmap)Image);
 						break;
 					case Effects.Rotate90:
+					case Effects.Rotate270:
 						MakeUndoable(new DrawableContainerBoundsChangeMemento(elements.AsIDrawableContainerList()), false);
-						foreach(DrawableContainer drawableContainer in elements) {
-							int angle = 270;
-							int ox = 0;
-							int oy = 0;
-							int centerX = Width>>1;
-							int centerY = Height>>1;
-							int px = drawableContainer.Bounds.X - centerX;
-							int py = centerY - drawableContainer.Bounds.Y;
-							double theta = Math.PI * angle / 180.0;
-							double x1 = Math.Cos(theta) * (px-ox) - Math.Sin(theta) * (py-oy) + ox;
-							double y1 = Math.Sin(theta) * (px-ox) + Math.Cos(theta) * (py-oy) + oy;
-
-							// Transform to Cartesian coordinates
-							px = (drawableContainer.Bounds.X+drawableContainer.Bounds.Width) - centerX;
-							py = centerY - (drawableContainer.Bounds.Y+drawableContainer.Bounds.Height);
-
-							double x2 = Math.Cos(theta) * (px-ox) - Math.Sin(theta) * (py-oy) + ox;
-							double y2 = Math.Sin(theta) * (px-ox) + Math.Cos(theta) * (py-oy) + oy;
-							x1 += centerY;
-							x2 += centerY;
-							y1 = centerX - y1;
-							y2 = centerX - y2;
-
-							// Calculate to rectangle
-							double newWidth = x2 - x1;
-							double newHeight = y2 - y1;
-							
-							RectangleF newRectangle = new RectangleF(
-								(float)x1,
-								(float)y1,
-								(float)newWidth,
-								(float)newHeight
-							);
-							LOG.DebugFormat("Bounds before {0}, bounds after {1}", drawableContainer.Bounds, newRectangle);
-							drawableContainer.ApplyBounds(newRectangle);
+						RotateFlipType rotateFlipType = RotateFlipType.Rotate270FlipNone;
+						if (effect == Effects.Rotate90) {
+							rotateFlipType = RotateFlipType.Rotate90FlipNone;
 						}
-						newImage = ImageHelper.RotateFlip((Bitmap)Image, RotateFlipType.Rotate90FlipNone);
+						foreach (DrawableContainer drawableContainer in elements) {
+							drawableContainer.Rotate(rotateFlipType);
+						}
+						newImage = ImageHelper.RotateFlip((Bitmap)Image, rotateFlipType);
 						break;
 				}