diff --git a/data/resources/image/BitmapResources/BitmapResources.res b/data/resources/image/BitmapResources/BitmapResources.res
index bdbd26b684..ed0420149a 100644
--- a/data/resources/image/BitmapResources/BitmapResources.res
+++ b/data/resources/image/BitmapResources/BitmapResources.res
@@ -333,8 +333,10 @@ Bookmarks.DeleteAllMarks                          = Bookmarks\DeleteAllMarks.png
 Bookmarks.EnableDisableAll                        = Bookmarks\EnableDisableAll.png
 Bookmarks.EnableDisableMark                       = Bookmarks\EnableDisableMark.png
 Bookmarks.Breakpoint                              = Bookmarks\Breakpoint.png
+Bookmarks.BreakpointConditional                   = Bookmarks\BreakpointConditional.png
 Bookmarks.DisabledBreakpoint                      = Bookmarks\DisabledBreakpoint.png
 Bookmarks.UnhealthyBreakpoint                     = Bookmarks\UnhealthyBreakpoint.png
+Bookmarks.UnhealthyBreakpointConditional          = Bookmarks\UnhealthyBreakpointConditional.png
 Bookmarks.CurrentLine                             = Bookmarks\CurrentLine.png
 
 #backend icons
diff --git a/data/resources/image/BitmapResources/Bookmarks/BreakpointConditional.png b/data/resources/image/BitmapResources/Bookmarks/BreakpointConditional.png
new file mode 100644
index 0000000000..0d41ebfedc
Binary files /dev/null and b/data/resources/image/BitmapResources/Bookmarks/BreakpointConditional.png differ
diff --git a/data/resources/image/BitmapResources/Bookmarks/UnhealthyBreakpointConditional.png b/data/resources/image/BitmapResources/Bookmarks/UnhealthyBreakpointConditional.png
new file mode 100644
index 0000000000..3519f7e641
Binary files /dev/null and b/data/resources/image/BitmapResources/Bookmarks/UnhealthyBreakpointConditional.png differ
diff --git a/src/Main/Base/Project/Src/Services/Debugger/BreakpointBookmark.cs b/src/Main/Base/Project/Src/Services/Debugger/BreakpointBookmark.cs
index 7cd8fddbc8..1aedbe0366 100644
--- a/src/Main/Base/Project/Src/Services/Debugger/BreakpointBookmark.cs
+++ b/src/Main/Base/Project/Src/Services/Debugger/BreakpointBookmark.cs
@@ -41,8 +41,15 @@ namespace ICSharpCode.SharpDevelop.Debugging
 		}
 		
 		public BreakpointAction Action {
-			get { return action; }
-			set { this.action = value; }
+			get {
+				return action;
+			}
+			set {
+				if (action != value) {
+					action = value;
+					Redraw();
+				}
+			}
 		}
 		
 		public virtual bool IsHealthy {
@@ -86,17 +93,19 @@ namespace ICSharpCode.SharpDevelop.Debugging
 		}
 		
 		public static readonly IImage BreakpointImage = new ResourceServiceImage("Bookmarks.Breakpoint");
+		public static readonly IImage BreakpointConditionalImage = new ResourceServiceImage("Bookmarks.BreakpointConditional");
 		public static readonly IImage DisabledBreakpointImage = new ResourceServiceImage("Bookmarks.DisabledBreakpoint");
 		public static readonly IImage UnhealthyBreakpointImage = new ResourceServiceImage("Bookmarks.UnhealthyBreakpoint");
+		public static readonly IImage UnhealthyBreakpointConditionalImage = new ResourceServiceImage("Bookmarks.UnhealthyBreakpointConditional");
 		
 		public override IImage Image {
 			get {
 				if (!this.IsEnabled)
 					return DisabledBreakpointImage;
 				else if (this.IsHealthy)
-					return BreakpointImage;
+					return this.Action == BreakpointAction.Break ? BreakpointImage : BreakpointConditionalImage;
 				else
-					return UnhealthyBreakpointImage;
+					return this.Action == BreakpointAction.Break ? UnhealthyBreakpointImage : UnhealthyBreakpointConditionalImage;
 			}
 		}
 		
diff --git a/src/Main/Base/Project/Src/Util/ExtensionMethods.cs b/src/Main/Base/Project/Src/Util/ExtensionMethods.cs
index 0a00f553d3..e2721c6e94 100644
--- a/src/Main/Base/Project/Src/Util/ExtensionMethods.cs
+++ b/src/Main/Base/Project/Src/Util/ExtensionMethods.cs
@@ -403,6 +403,7 @@ namespace ICSharpCode.SharpDevelop
 			} else {
 				r.Click += delegate { item.PerformClick(); };
 			}
+			r.IsChecked = item.Checked;
 			return r;
 		}
 		
diff --git a/src/Main/StartUp/Project/Resources/BitmapResources.resources b/src/Main/StartUp/Project/Resources/BitmapResources.resources
index 1d2a698d66..9fa8d0de13 100644
Binary files a/src/Main/StartUp/Project/Resources/BitmapResources.resources and b/src/Main/StartUp/Project/Resources/BitmapResources.resources differ