diff --git a/src/company_cmd.cpp b/src/company_cmd.cpp
index 0357e337ea..9d4a15e426 100644
--- a/src/company_cmd.cpp
+++ b/src/company_cmd.cpp
@@ -937,7 +937,10 @@ CommandCost CmdCompanyCtrl(TileIndex tile, DoCommandFlag flags, uint32 p1, uint3
 			Game::NewEvent(new ScriptEventCompanyBankrupt(c_index));
 			CompanyAdminRemove(c_index, (CompanyRemoveReason)reason);
 
-			if (StoryPage::GetNumItems() == 0 || Goal::GetNumItems() == 0) InvalidateWindowData(WC_MAIN_TOOLBAR, 0);
+			if (StoryPage::GetNumItems() == 0 || Goal::GetNumItems() == 0) {
+				InvalidateWindowData(WC_MAIN_TOOLBAR, 0);
+				InvalidateWindowData(WC_MAIN_TOOLBAR_RIGHT, 0);
+			}
 			break;
 		}
 
diff --git a/src/main_gui.cpp b/src/main_gui.cpp
index 9d13deef66..113ce8a864 100644
--- a/src/main_gui.cpp
+++ b/src/main_gui.cpp
@@ -461,6 +461,7 @@ struct MainWindow : Window
 		if (!gui_scope) return;
 		/* Forward the message to the appropriate toolbar (ingame or scenario editor) */
 		InvalidateWindowData(WC_MAIN_TOOLBAR, 0, data, true);
+		InvalidateWindowData(WC_MAIN_TOOLBAR_RIGHT, 0, data, true);
 	}
 
 	static HotkeyList hotkeys;
diff --git a/src/script/api/script_window.hpp b/src/script/api/script_window.hpp
index 680c3f2d85..e61fa1a532 100644
--- a/src/script/api/script_window.hpp
+++ b/src/script/api/script_window.hpp
@@ -135,6 +135,13 @@ public:
 		 */
 		WC_MAIN_TOOLBAR                              = ::WC_MAIN_TOOLBAR,
 
+		/**
+		 * Main toolbar (the long bar at the top); %Window numbers:
+		 *   - 0 = #ToolbarNormalWidgets
+		 *   - 0 = #ToolbarEditorWidgets
+		 */
+		WC_MAIN_TOOLBAR_RIGHT                        = ::WC_MAIN_TOOLBAR_RIGHT,
+
 		/**
 		 * Statusbar (at the bottom of your screen); %Window numbers:
 		 *   - 0 = #StatusbarWidgets
diff --git a/src/toolbar_gui.cpp b/src/toolbar_gui.cpp
index fde6ed284c..edacf68c64 100644
--- a/src/toolbar_gui.cpp
+++ b/src/toolbar_gui.cpp
@@ -58,6 +58,7 @@ RailType _last_built_railtype;
 RoadType _last_built_roadtype;
 
 static ScreenshotType _confirmed_screenshot_type; ///< Screenshot type the current query is about to confirm.
+int _last_clicked_toolbar_idx = 0;
 
 /** Toobar modes */
 enum ToolbarMode {
@@ -170,7 +171,17 @@ public:
  */
 static void PopupMainToolbMenu(Window *w, int widget, DropDownList *list, int def)
 {
-	ShowDropDownList(w, list, def, widget, 0, true, true);
+	if (!_settings_client.gui.vertical_toolbar) {
+		ShowDropDownList(w, list, def, widget, 0, true, true);
+	} else {
+		Rect wi_rect;
+		NWidgetCore *nwi = w->GetWidget<NWidgetCore>(widget);
+		wi_rect.left   = ((int)nwi->pos_x < _screen.width / 2) ? nwi->pos_x + nwi->current_x - 1 : nwi->pos_x - nwi->current_x;
+		wi_rect.right  = ((int)nwi->pos_x < _screen.width / 2) ? nwi->pos_x + nwi->current_x * 2 : nwi->pos_x - 1;
+		wi_rect.top    = nwi->pos_y;
+		wi_rect.bottom = nwi->pos_y + nwi->current_y - 1;
+		ShowDropDownListAt(w, list, def, widget, wi_rect, nwi->colour, true, true);
+	}
 	if (_settings_client.sound.click_beep) SndPlayFx(SND_15_BEEP);
 }
 
@@ -1796,8 +1807,10 @@ enum MainToolbarHotkeys {
 /** Main toolbar. */
 struct MainToolbarWindow : Window {
 	CallBackFunction last_started_action; ///< Last started user action.
+	int *clickedFlag;
+	int clickedValue;
 
-	MainToolbarWindow(WindowDesc *desc) : Window(desc)
+	MainToolbarWindow(WindowDesc *desc, int *clickedFlag = NULL, int clickedValue = 0) : Window(desc), clickedFlag(clickedFlag), clickedValue(clickedValue)
 	{
 		this->InitNested(0);
 
@@ -1829,11 +1842,15 @@ struct MainToolbarWindow : Window {
 
 	virtual void OnClick(Point pt, int widget, int click_count)
 	{
+		if (clickedFlag)
+			*clickedFlag = clickedValue;
 		if (_game_mode != GM_MENU && !this->IsWidgetDisabled(widget)) _toolbar_button_procs[widget](this);
 	}
 
 	virtual void OnDropdownSelect(int widget, int index)
 	{
+		if (clickedFlag)
+			*clickedFlag = clickedValue;
 		CallBackFunction cbf = _menu_clicked_procs[widget](index);
 		if (cbf != CBF_NONE) this->last_started_action = cbf;
 	}
@@ -2425,9 +2442,9 @@ void AllocateToolbar()
 		new ScenarioEditorToolbarWindow(&_toolb_scen_desc);
 	} else {
 		if (_settings_client.gui.vertical_toolbar) {
-			MainToolbarWindow *w = new MainToolbarWindow(&_toolb_vertical_left_desc);
+			MainToolbarWindow *w = new MainToolbarWindow(&_toolb_vertical_left_desc, &_last_clicked_toolbar_idx, 0);
 			w->left = 0;
-			w = new MainToolbarWindow(&_toolb_vertical_right_desc);
+			w = new MainToolbarWindow(&_toolb_vertical_right_desc, &_last_clicked_toolbar_idx, 1);
 			w->left = _screen.width - w->width;
 			SetDirtyBlocks(0, w->top, _screen.width, w->top + w->height);
 		} else {
diff --git a/src/toolbar_gui.h b/src/toolbar_gui.h
index acfe0ed418..3461c22902 100644
--- a/src/toolbar_gui.h
+++ b/src/toolbar_gui.h
@@ -18,4 +18,6 @@ void ToggleDirtyBlocks();
 
 void ResetTabletWindow();
 
+extern int _last_clicked_toolbar_idx;
+
 #endif /* TOOLBAR_GUI_H */
diff --git a/src/window.cpp b/src/window.cpp
index 77a94da937..f7590fc25b 100644
--- a/src/window.cpp
+++ b/src/window.cpp
@@ -1261,6 +1261,7 @@ static uint GetWindowZPriority(const Window *w)
 			++z_priority;
 
 		case WC_MAIN_TOOLBAR:
+		case WC_MAIN_TOOLBAR_RIGHT:
 		case WC_STATUS_BAR:
 			++z_priority;
 
@@ -1475,6 +1476,10 @@ void Window::FindWindowPlacementAndResize(int def_width, int def_height)
 
 		int enlarge_x = max(min(def_width  - this->width,  _screen.width - this->width),  0);
 		int enlarge_y = max(min(def_height - this->height, free_height   - this->height), 0);
+		if (wt && _settings_client.gui.vertical_toolbar &&
+			enlarge_x > _screen.width - wt->width * 2) {
+			//enlarge_x = _screen.width - wt->width * 2;
+		}
 
 		/* X and Y has to go by step.. calculate it.
 		 * The cast to int is necessary else x/y are implicitly casted to
@@ -1525,7 +1530,11 @@ static bool IsGoodAutoPlace1(int left, int top, int width, int height, Point &po
 	int bottom = height + top;
 
 	const Window *main_toolbar = FindWindowByClass(WC_MAIN_TOOLBAR);
-	if (left < 0 || (main_toolbar != NULL && top < main_toolbar->height) || right > _screen.width || bottom > _screen.height) return false;
+	if (!_settings_client.gui.vertical_toolbar || !main_toolbar) {
+		if (left < 0 || (main_toolbar != NULL && top < main_toolbar->height) || right > _screen.width || bottom > _screen.height) return false;
+	} else {
+		if (left < main_toolbar->width || top < 0 || right > _screen.width - main_toolbar->width * 2 || bottom > _screen.height) return false;
+	}
 
 	/* Make sure it is not obscured by any window. */
 	const Window *w;
@@ -1636,6 +1645,10 @@ static Point GetAutoPlacePosition(int width, int height)
 	 * of (+5, +5)
 	 */
 	int left = 0, top = 24;
+	if (_settings_client.gui.vertical_toolbar) {
+		left = main_toolbar != NULL ? main_toolbar->width : 0;
+		top = 0;
+	}
 
 restart:
 	FOR_ALL_WINDOWS_FROM_BACK(w) {
@@ -1663,15 +1676,12 @@ Point GetToolbarAlignedWindowPosition(int window_width)
 	assert(w != NULL);
 	Point pt;
 	if (_settings_client.gui.vertical_toolbar) {
-		pt.x = _current_text_dir == TD_RTL ? w->left + w->width : _screen.width - window_width - w->width;
+		// Retermine if the window was opened from the left or the right toolbar
+		pt.x = (_last_clicked_toolbar_idx == 0) ? w->left + w->width : _screen.width - w->width - window_width - 1;
 		pt.y = w->top;
 	} else {
+		pt.x = _current_text_dir == TD_RTL ? w->left : (w->left + w->width) - window_width;
 		pt.y = w->top + w->height;
-		if (_settings_client.gui.touchscreen_mode != TSC_NONE) {
-			pt.x = _current_text_dir == TD_RTL ? 0 : (_screen.width - window_width);
-		} else {
-			pt.x = _current_text_dir == TD_RTL ? w->left : (w->left + w->width) - window_width;
-		}
 	}
 	return pt;
 }
@@ -1705,13 +1715,9 @@ static Point LocalGetWindowPlacement(const WindowDesc *desc, int16 sm_width, int
 			(w = FindWindowById(desc->parent_cls, window_number)) != NULL &&
 			w->left < _screen.width - 20 && w->left > -60 && w->top < _screen.height - 20) {
 
-		if (_settings_client.gui.touchscreen_mode != TSC_NONE) {
-			pt.x = _current_text_dir == TD_RTL ? 0 : (_screen.width - default_width);
-		} else {
-			pt.x = w->left + ((desc->parent_cls == WC_BUILD_TOOLBAR || desc->parent_cls == WC_SCEN_LAND_GEN) ? 0 : 10);
-			if (pt.x > _screen.width + 10 - default_width) {
-				pt.x = (_screen.width + 10 - default_width) - 20;
-			}
+		pt.x = w->left + ((desc->parent_cls == WC_BUILD_TOOLBAR || desc->parent_cls == WC_SCEN_LAND_GEN) ? 0 : 10);
+		if (pt.x > _screen.width + 10 - default_width) {
+			pt.x = (_screen.width + 10 - default_width) - 20;
 		}
 
 		pt.y = w->top + ((desc->parent_cls == WC_BUILD_TOOLBAR || desc->parent_cls == WC_SCEN_LAND_GEN) ? w->height : 10);
@@ -2064,6 +2070,7 @@ static void EnsureVisibleCaption(Window *w, int nx, int ny)
 
 		/* Make sure the title bar isn't hidden behind the main tool bar or the status bar. */
 		PreventHiding(&nx, &ny, caption_rect, FindWindowById(WC_MAIN_TOOLBAR, 0), w->left, PHD_DOWN);
+		PreventHiding(&nx, &ny, caption_rect, FindWindowById(WC_MAIN_TOOLBAR_RIGHT, 0), w->left, PHD_DOWN);
 		PreventHiding(&nx, &ny, caption_rect, FindWindowById(WC_STATUS_BAR,   0), w->left, PHD_UP);
 	}
 
@@ -2124,6 +2131,7 @@ void ResizeWindow(Window *w, int delta_x, int delta_y, bool clamp_to_screen)
  */
 int GetMainViewTop()
 {
+	if (_settings_client.gui.vertical_toolbar) return 0;
 	Window *w = FindWindowById(WC_MAIN_TOOLBAR, 0);
 	return (w == NULL) ? 0 : w->top + w->height;
 }
@@ -3290,6 +3298,7 @@ restart_search:
 		if (w->window_class != WC_MAIN_WINDOW &&
 				w->window_class != WC_SELECT_GAME &&
 				w->window_class != WC_MAIN_TOOLBAR &&
+				w->window_class != WC_MAIN_TOOLBAR_RIGHT &&
 				w->window_class != WC_STATUS_BAR &&
 				w->window_class != WC_TOOLTIPS &&
 				(w->flags & WF_STICKY) == 0) { // do not delete windows which are 'pinned'
@@ -3506,6 +3515,7 @@ void RelocateAllWindows(int neww, int newh)
 				continue;
 
 			case WC_MAIN_TOOLBAR:
+			case WC_MAIN_TOOLBAR_RIGHT:
 				ResizeWindow(w, min(neww, w->window_desc->default_width) - w->width, 0, false);
 
 				top = w->top;