diff -r 4fb585796f09 src/depot_gui.cpp
--- a/src/depot_gui.cpp	Fri Mar 19 13:55:02 2010 +0100
+++ b/src/depot_gui.cpp	Fri Mar 19 13:55:06 2010 +0100
@@ -888,12 +888,19 @@
 
 			VehicleID new_vehicle_over = INVALID_VEHICLE;
 
-			if (gdvp.head != NULL && gdvp.wagon != NULL && 
-					gdvp.head != gdvp.wagon && 
-					gdvp.wagon->index != this->sel && 
-					gdvp.wagon->Previous()->index != this->sel) {
-				/* Drag over an existing wagon */
-				new_vehicle_over = gdvp.wagon->index;
+			if (gdvp.head != NULL) {
+				if (gdvp.wagon == NULL && gdvp.head->Last()->index != this->sel) {
+					/* Drag at the end of a train. As we cannot move a wagon at the
+					   begin of a train, head index isn't used to denote a drag & drop
+					   destination inside a train. This head index is then used to indicate 
+					   that we are inserting a wagon at the end of the train. */
+					new_vehicle_over = gdvp.head->index;
+				} else if (gdvp.wagon != NULL && gdvp.head != gdvp.wagon && 
+							gdvp.wagon->index != this->sel && 
+							gdvp.wagon->Previous()->index != this->sel) {
+					/* Drag over an existing wagon */
+					new_vehicle_over = gdvp.wagon->index;
+				}
 			}
 
 			if (this->vehicle_over == new_vehicle_over) return;
diff -r 4fb585796f09 src/train_gui.cpp
--- a/src/train_gui.cpp	Fri Mar 19 13:55:02 2010 +0100
+++ b/src/train_gui.cpp	Fri Mar 19 13:55:06 2010 +0100
@@ -48,6 +48,23 @@
 	}
 }
 
+int HighlightDragPosition(bool rtl, int px, int max_width, Point *offset, int width)
+{
+	Dimension sprite_size = GetSpriteSize(SPR_ARROW_UP);
+	int sprite_size_width = sprite_size.width;
+
+	if (rtl ? px + sprite_size_width <= 0 : px - sprite_size_width >= max_width) return 0;
+
+	int drag_offset_x = offset->x - (width + (rtl ? -sprite_size_width : sprite_size_width)) / 2;
+	uint drag_x = px + (rtl ? -drag_offset_x : drag_offset_x);
+	uint drag_y = offset->y - (sprite_size.height / 2);
+
+	DrawSprite(SPR_ARROW_DOWN, PAL_NONE, drag_x, drag_y + 2);
+	DrawSprite(SPR_ARROW_UP, PAL_NONE, drag_x, drag_y + 7);
+
+	return sprite_size.width;
+}
+
 /**
  * Draws an image of a whole train
  * @param v         Front vehicle
@@ -76,13 +93,17 @@
 
 	int px = rtl ? max_width + skip : -skip;
 	bool sel_articulated = false;
+	bool dragging = drag_dest != INVALID_VEHICLE;
+	bool drag_at_end_of_train = (drag_dest == v->index); // Head index is used to mark dragging at the end of train
+	Point offset;
+	int width = 0;
 	for (; v != NULL && (rtl ? px > 0 : px < max_width); v = v->Next()) {
-		Point offset;
-		int width = Train::From(v)->GetDisplayImageWidth(&offset);
+		width = Train::From(v)->GetDisplayImageWidth(&offset);
 
-		if (drag_dest != INVALID_VEHICLE && drag_dest == v->index) {
-			/* Highlight the drag & drop destination inside train: insert a 5px wide space. */
-			px += rtl ? -5 : 5;
+		if (dragging && !drag_at_end_of_train && drag_dest == v->index) {
+			/* Highlight the drag & drop destination inside train. */
+			int highlight_width = HighlightDragPosition(rtl, px, max_width, &offset, width);
+			px += rtl ? -highlight_width : highlight_width;
 		}
 
 		if (rtl ? px + width > 0 : px - width < max_width) {
@@ -108,6 +129,11 @@
 		px += rtl ? -width : width;
 	}
 
+	if (dragging && drag_at_end_of_train) {
+		/* Highlight the drag & drop destination at the end of train. */
+		HighlightDragPosition(rtl, px, max_width, &offset, width);
+	}
+
 	if (highlight_l != highlight_r) {
 		/* Draw the highlight. Now done after drawing all the engines, as
 		 * the next engine after the highlight could overlap it. */