diff --git a/src/apps/icon-o-matic/IconEditorApp.cpp b/src/apps/icon-o-matic/IconEditorApp.cpp
index d5c0231bac..c58ef8714a 100644
--- a/src/apps/icon-o-matic/IconEditorApp.cpp
+++ b/src/apps/icon-o-matic/IconEditorApp.cpp
@@ -62,7 +62,9 @@ IconEditorApp::IconEditorApp()
 
 	  fLastOpenPath(""),
 	  fLastSavePath(""),
-	  fLastExportPath("")
+	  fLastExportPath(""),
+
+	  fMessageAfterSave(NULL)
 {
 }
 
@@ -76,6 +78,8 @@ IconEditorApp::~IconEditorApp()
 
 	delete fOpenPanel;
 	delete fSavePanel;
+
+	delete fMessageAfterSave;
 }
 
 // #pragma mark -
@@ -84,7 +88,9 @@ IconEditorApp::~IconEditorApp()
 bool
 IconEditorApp::QuitRequested()
 {
-	// TODO: ask main window if quitting is ok
+	if (!_CheckSaveIcon(CurrentMessage()))
+		return false;
+
 	_StoreSettings();
 
 	fMainWindow->Lock();
@@ -103,14 +109,12 @@ IconEditorApp::MessageReceived(BMessage* message)
 			_MakeIconEmpty();
 			break;
 		case MSG_OPEN: {
-//			fOpenPanel->Refresh();
 			BMessage openMessage(B_REFS_RECEIVED);
 			fOpenPanel->SetMessage(&openMessage);
 			fOpenPanel->Show();
 			break;
 		}
 		case MSG_APPEND: {
-//			fOpenPanel->Refresh();
 			BMessage openMessage(B_REFS_RECEIVED);
 			openMessage.AddBool("append", true);
 			fOpenPanel->SetMessage(&openMessage);
@@ -126,6 +130,7 @@ IconEditorApp::MessageReceived(BMessage* message)
 				saver = fDocument->ExportSaver();
 			if (saver) {
 				saver->Save(fDocument);
+				_PickUpActionBeforeSave();
 				break;
 			} // else fall through
 		}
@@ -153,6 +158,7 @@ IconEditorApp::MessageReceived(BMessage* message)
 						else
 							fDocument->SetExportSaver(saver);
 						saver->Save(fDocument);
+						_PickUpActionBeforeSave();
 					}
 				}
 				_SyncPanels(fSavePanel, fOpenPanel);
@@ -267,9 +273,61 @@ IconEditorApp::ArgvReceived(int32 argc, char** argv)
 
 // #pragma mark -
 
+// _CheckSaveIcon
+bool
+IconEditorApp::_CheckSaveIcon(const BMessage* currentMessage)
+{
+	if (fDocument->IsEmpty() || fDocument->CommandStack()->IsSaved())
+		return true;
+
+	BAlert* alert = new BAlert("save", "Save changes to current icon?",
+		"Discard", "Cancel", "Save");
+	int32 choice = alert->Go();
+	switch (choice) {
+		case 0:
+			// discard
+			return true;
+		case 1:
+			// cancel
+			return false;
+		case 2:
+		default:
+			// cancel (save first) but pick what we were doing before
+			PostMessage(MSG_SAVE);
+			if (currentMessage) {
+				delete fMessageAfterSave;
+				fMessageAfterSave = new BMessage(*currentMessage);
+			}
+			return false;
+	}
+}
+
+// _PickUpActionBeforeSave
+void
+IconEditorApp::_PickUpActionBeforeSave()
+{
+	if (fDocument->WriteLock()) {
+		fDocument->CommandStack()->Save();
+		fDocument->WriteUnlock();
+	}
+
+	if (!fMessageAfterSave)
+		return;
+
+	PostMessage(fMessageAfterSave);
+	delete fMessageAfterSave;
+	fMessageAfterSave = NULL;
+}
+
+// #pragma mark -
+
+// _MakeIconEmpty
 void
 IconEditorApp::_MakeIconEmpty()
 {
+	if (!_CheckSaveIcon(CurrentMessage()))
+		return;
+
 	bool mainWindowLocked = fMainWindow && fMainWindow->Lock();
 
 	AutoWriteLocker locker(fDocument);
@@ -289,6 +347,9 @@ IconEditorApp::_MakeIconEmpty()
 void
 IconEditorApp::_Open(const entry_ref& ref, bool append)
 {
+	if (!_CheckSaveIcon(CurrentMessage()))
+		return;
+
 	BFile file(&ref, B_READ_ONLY);
 	if (file.InitCheck() < B_OK)
 		return;
@@ -390,6 +451,9 @@ void
 IconEditorApp::_Open(const BMessenger& externalObserver,
 					 const uint8* data, size_t size)
 {
+	if (!_CheckSaveIcon(CurrentMessage()))
+		return;
+
 	if (!externalObserver.IsValid())
 		return;
 
diff --git a/src/apps/icon-o-matic/IconEditorApp.h b/src/apps/icon-o-matic/IconEditorApp.h
index 41c0b30910..d19ee5663d 100644
--- a/src/apps/icon-o-matic/IconEditorApp.h
+++ b/src/apps/icon-o-matic/IconEditorApp.h
@@ -63,6 +63,9 @@ class IconEditorApp : public BApplication {
 	// IconEditorApp
 
  private:
+			bool				_CheckSaveIcon(const BMessage* currentMessage);
+			void				_PickUpActionBeforeSave();
+
 			void				_MakeIconEmpty();
 			void				_Open(const entry_ref& ref,
 									  bool append = false);
@@ -89,6 +92,8 @@ class IconEditorApp : public BApplication {
 			BString				fLastOpenPath;
 			BString				fLastSavePath;
 			BString				fLastExportPath;
+
+			BMessage*			fMessageAfterSave;
 };
 
 #endif // ICON_EDITOR_APP_H
diff --git a/src/apps/icon-o-matic/MainWindow.cpp b/src/apps/icon-o-matic/MainWindow.cpp
index 1df0a59aed..eeaf935175 100644
--- a/src/apps/icon-o-matic/MainWindow.cpp
+++ b/src/apps/icon-o-matic/MainWindow.cpp
@@ -215,6 +215,10 @@ case MSG_PATH_SELECTED: {
 	VectorPath* path;
 	if (message->FindPointer("path", (void**)&path) < B_OK)
 		path = NULL;
+
+	fPathListView->SetCurrentShape(NULL);
+	fStyleListView->SetCurrentShape(NULL);
+	fTransformerListView->SetShape(NULL);
 	
 	fState->DeleteManipulators();
 	if (fDocument->Icon()->Paths()->HasPath(path)) {
@@ -223,7 +227,8 @@ case MSG_PATH_SELECTED: {
 	}
 	break;
 }
-case MSG_STYLE_SELECTED: {
+case MSG_STYLE_SELECTED:
+case MSG_STYLE_TYPE_CHANGED: {
 	Style* style;
 	if (message->FindPointer("style", (void**)&style) < B_OK)
 		style = NULL;
@@ -231,14 +236,13 @@ case MSG_STYLE_SELECTED: {
 		style = NULL;
 
 	fStyleView->SetStyle(style);
-	break;
-}
-case MSG_GRADIENT_SELECTED: {
-	// if there is a gradient, add a transform box around it
-	Gradient* gradient;
-	if (message->FindPointer("gradient", (void**)&gradient) < B_OK)
-		gradient = NULL;
+	fPathListView->SetCurrentShape(NULL);
+	fStyleListView->SetCurrentShape(NULL);
+	fTransformerListView->SetShape(NULL);
+
 	fState->DeleteManipulators();
+	Gradient* gradient = style ? style->Gradient() : NULL;
+
 	if (gradient) {
 		TransformGradientBox* transformBox
 			= new (nothrow) TransformGradientBox(fCanvasView,
diff --git a/src/apps/icon-o-matic/document/Document.cpp b/src/apps/icon-o-matic/document/Document.cpp
index 02b63492e8..ade4d275cc 100644
--- a/src/apps/icon-o-matic/document/Document.cpp
+++ b/src/apps/icon-o-matic/document/Document.cpp
@@ -12,7 +12,10 @@
 #include "CommandStack.h"
 #include "DocumentSaver.h"
 #include "Icon.h"
+#include "PathContainer.h"
 #include "Selection.h"
+#include "ShapeContainer.h"
+#include "StyleContainer.h"
 
 #include <Entry.h>
 
@@ -112,4 +115,12 @@ Document::MakeEmpty(bool includingSavers)
 	}
 }
 
+// IsEmpty
+bool
+Document::IsEmpty() const
+{
+	return fIcon->Styles()->CountStyles() == 0
+		&& fIcon->Paths()->CountPaths() == 0
+		&& fIcon->Shapes()->CountShapes() == 0; 
+}
 
diff --git a/src/apps/icon-o-matic/document/Document.h b/src/apps/icon-o-matic/document/Document.h
index b26bdf642a..7863b0c92d 100644
--- a/src/apps/icon-o-matic/document/Document.h
+++ b/src/apps/icon-o-matic/document/Document.h
@@ -57,6 +57,8 @@ class Document : public RWLocker,
 
 			void				MakeEmpty(bool includingSavers = true);
 
+			bool				IsEmpty() const;
+
  private:
 			BPrivate::Icon::Icon* fIcon;
 			::CommandStack*		fCommandStack;
diff --git a/src/apps/icon-o-matic/generic/gui/ListViews.cpp b/src/apps/icon-o-matic/generic/gui/ListViews.cpp
index cd95f8c4db..f2f2dccd47 100644
--- a/src/apps/icon-o-matic/generic/gui/ListViews.cpp
+++ b/src/apps/icon-o-matic/generic/gui/ListViews.cpp
@@ -533,9 +533,10 @@ DragSortableListView::MouseWheelChanged(float x, float y)
 void
 DragSortableListView::ObjectChanged(const Observable* object)
 {
-	if (object != fSelection || fModifyingSelection)
+	if (object != fSelection || fModifyingSelection || fSyncingToSelection)
 		return;
 
+//printf("%s - syncing start\n", Name());
 	fSyncingToSelection = true;
 
 	// try to sync to Selection
@@ -567,6 +568,7 @@ DragSortableListView::ObjectChanged(const Observable* object)
 	}
 
 	fSyncingToSelection = false;
+//printf("%s - done\n", Name());
 }
 
 // #pragma mark -
@@ -813,7 +815,7 @@ DragSortableListView::SelectionChanged()
 {
 //printf("%s::SelectionChanged()", typeid(*this).name());
 	// modify global Selection
-	if (!fSelection)
+	if (!fSelection || fSyncingToSelection)
 		return;
 
 	fModifyingSelection = true;
diff --git a/src/apps/icon-o-matic/gui/PathListView.cpp b/src/apps/icon-o-matic/gui/PathListView.cpp
index 7244c95216..eb3b7fcb55 100644
--- a/src/apps/icon-o-matic/gui/PathListView.cpp
+++ b/src/apps/icon-o-matic/gui/PathListView.cpp
@@ -623,7 +623,7 @@ PathListView::PathAdded(VectorPath* path, int32 index)
 		return;
 
 	if (_AddPath(path, index))
-		Select(CountItems() - 1);
+		Select(index);
 
 	UnlockLooper();
 }
diff --git a/src/apps/icon-o-matic/gui/ShapeListView.cpp b/src/apps/icon-o-matic/gui/ShapeListView.cpp
index dc78ee1958..3bdb154a17 100644
--- a/src/apps/icon-o-matic/gui/ShapeListView.cpp
+++ b/src/apps/icon-o-matic/gui/ShapeListView.cpp
@@ -1,5 +1,5 @@
 /*
- * Copyright 2006, Haiku.
+ * Copyright 2006-2007, Haiku Inc. All rights reserved.
  * Distributed under the terms of the MIT License.
  *
  * Authors:
@@ -129,7 +129,6 @@ ShapeListView::~ShapeListView()
 void
 ShapeListView::SelectionChanged()
 {
-
 	SimpleListView::SelectionChanged();
 
 	if (!fSyncingToSelection) {
@@ -387,7 +386,8 @@ ShapeListView::ShapeAdded(Shape* shape, int32 index)
 	if (!LockLooper())
 		return;
 
-	_AddShape(shape, index);
+	if (_AddShape(shape, index))
+		Select(index);
 
 	UnlockLooper();
 }
diff --git a/src/apps/icon-o-matic/gui/StyleListView.cpp b/src/apps/icon-o-matic/gui/StyleListView.cpp
index cc5ae4920b..9d3b2e01b5 100644
--- a/src/apps/icon-o-matic/gui/StyleListView.cpp
+++ b/src/apps/icon-o-matic/gui/StyleListView.cpp
@@ -555,10 +555,8 @@ StyleListView::StyleAdded(Style* style, int32 index)
 	if (!LockLooper())
 		return;
 
-	// NOTE: shapes are always added at the end
-	// of the list, so the sorting is synced...
 	if (_AddStyle(style, index))
-		Select(CountItems() - 1);
+		Select(index);
 
 	UnlockLooper();
 }
diff --git a/src/apps/icon-o-matic/gui/StyleView.cpp b/src/apps/icon-o-matic/gui/StyleView.cpp
index 3aa3e0ec89..0925cdb760 100644
--- a/src/apps/icon-o-matic/gui/StyleView.cpp
+++ b/src/apps/icon-o-matic/gui/StyleView.cpp
@@ -267,7 +267,7 @@ StyleView::ObjectChanged(const Observable* object)
 		// TODO: is this really necessary?
 		controlGradient->SetTransform(*fGradient);
 
-		if (*fGradient != *controlGradient) {
+		if (!fGradient->ColorStepsAreEqual(*controlGradient)) {
 			if (fCommandStack) {
 				fCommandStack->Perform(
 					new (nothrow) SetGradientCommand(
@@ -279,7 +279,7 @@ StyleView::ObjectChanged(const Observable* object)
 			_TransferGradientStopColor();
 		}
 	} else if (object == fGradient) {
-		if (*fGradient != *controlGradient) {
+		if (!fGradient->ColorStepsAreEqual(*controlGradient)) {
 			fGradientControl->SetGradient(fGradient);
 			_MarkType(fGradientType->Menu(), fGradient->Type());
 			// transfer the current gradient color to the current color
@@ -288,7 +288,7 @@ StyleView::ObjectChanged(const Observable* object)
 	} else if (object == fStyle) {
 		// maybe the gradient was added or removed
 		// or the color changed
-		_SetGradient(fStyle->Gradient());
+		_SetGradient(fStyle->Gradient(), false, true);
 		if (fCurrentColor && !fStyle->Gradient())
 			fCurrentColor->SetColor(fStyle->Color());
 	} else if (object == fCurrentColor) {
@@ -361,7 +361,7 @@ StyleView::SetCurrentColor(CurrentColor* color)
 
 // _SetGradient
 void
-StyleView::_SetGradient(Gradient* gradient, bool forceControlUpdate)
+StyleView::_SetGradient(Gradient* gradient, bool forceControlUpdate, bool sendMessage)
 {
 	if (!forceControlUpdate && fGradient == gradient)
 		return;
@@ -387,9 +387,9 @@ StyleView::_SetGradient(Gradient* gradient, bool forceControlUpdate)
 		_MarkType(fGradientType->Menu(), -1);
 	}
 
-	if (Window()) {
-		BMessage message(MSG_GRADIENT_SELECTED);
-		message.AddPointer("gradient", (void*)fGradient);
+	if (sendMessage) {
+		BMessage message(MSG_STYLE_TYPE_CHANGED);
+		message.AddPointer("style", fStyle);
 		Window()->PostMessage(&message);
 	}
 }
diff --git a/src/apps/icon-o-matic/gui/StyleView.h b/src/apps/icon-o-matic/gui/StyleView.h
index 793e25f057..96f5b04b0b 100644
--- a/src/apps/icon-o-matic/gui/StyleView.h
+++ b/src/apps/icon-o-matic/gui/StyleView.h
@@ -31,7 +31,7 @@ using namespace BPrivate::Icon;
 // TODO: write lock the document when changing something...
 
 enum {
-	MSG_GRADIENT_SELECTED	= 'grsl',
+	MSG_STYLE_TYPE_CHANGED	= 'stch',
 };
 
 class StyleView : public BView,
@@ -59,7 +59,8 @@ class StyleView : public BView,
 
  private:
 			void				_SetGradient(Gradient* gradient,
-											 bool forceControlUpdate = false);
+											 bool forceControlUpdate = false,
+											 bool sendMessage = false);
 			void				_MarkType(BMenu* menu,
 										  int32 type) const;
 			void				_SetStyleType(int32 type);
diff --git a/src/apps/icon-o-matic/shape/commands/AddShapesCommand.cpp b/src/apps/icon-o-matic/shape/commands/AddShapesCommand.cpp
index 20c31989bc..89090fda99 100644
--- a/src/apps/icon-o-matic/shape/commands/AddShapesCommand.cpp
+++ b/src/apps/icon-o-matic/shape/commands/AddShapesCommand.cpp
@@ -72,8 +72,6 @@ AddShapesCommand::Perform()
 				fContainer->RemoveShape(fShapes[j]);
 			break;
 		}
-		if (fSelection)
-			fSelection->Select(fShapes[i], i > 0);
 		index++;
 	}
 	fShapesAdded = true;
diff --git a/src/libs/icon/style/Gradient.cpp b/src/libs/icon/style/Gradient.cpp
index 609bfcfc4e..7b0e2e0d27 100644
--- a/src/libs/icon/style/Gradient.cpp
+++ b/src/libs/icon/style/Gradient.cpp
@@ -227,25 +227,8 @@ Gradient::operator=(const Gradient& other)
 bool
 Gradient::operator==(const Gradient& other) const
 {
-	if (Transformable::operator==(other)) {
-		int32 count = CountColors();
-		if (count == other.CountColors() &&
-			fType == other.fType &&
-			fInterpolation == other.fInterpolation &&
-			fInheritTransformation == other.fInheritTransformation) {
-	
-			bool equal = true;
-			for (int32 i = 0; i < count; i++) {
-				color_step* ourStep = ColorAtFast(i);
-				color_step* otherStep = other.ColorAtFast(i);
-				if (*ourStep != *otherStep) {
-					equal = false;
-					break;
-				}
-			}
-			return equal;
-		}
-	}
+	if (Transformable::operator==(other))
+		return ColorStepsAreEqual(other);
 	return false;
 }
 
@@ -256,6 +239,30 @@ Gradient::operator!=(const Gradient& other) const
 	return !(*this == other);
 }
 
+// ColorStepsAreEqual
+bool
+Gradient::ColorStepsAreEqual(const Gradient& other) const
+{
+	int32 count = CountColors();
+	if (count == other.CountColors() &&
+		fType == other.fType &&
+		fInterpolation == other.fInterpolation &&
+		fInheritTransformation == other.fInheritTransformation) {
+
+		bool equal = true;
+		for (int32 i = 0; i < count; i++) {
+			color_step* ourStep = ColorAtFast(i);
+			color_step* otherStep = other.ColorAtFast(i);
+			if (*ourStep != *otherStep) {
+				equal = false;
+				break;
+			}
+		}
+		return equal;
+	}
+	return false;
+}
+
 // SetColors
 void
 Gradient::SetColors(const Gradient& other)
diff --git a/src/libs/icon/style/Gradient.h b/src/libs/icon/style/Gradient.h
index aae25fcd20..ac1f82938a 100644
--- a/src/libs/icon/style/Gradient.h
+++ b/src/libs/icon/style/Gradient.h
@@ -78,6 +78,8 @@ class Gradient : public Transformable {
 
 			bool				operator==(const Gradient& other) const;
 			bool				operator!=(const Gradient& other) const;
+			bool				ColorStepsAreEqual(
+									const Gradient& other) const;
 
 			void				SetColors(const Gradient& other);