diff --git a/src/lang/english.txt b/src/lang/english.txt
--- a/src/lang/english.txt
+++ b/src/lang/english.txt
@@ -4137,6 +4137,11 @@ STR_VEHICLE_STATUS_HEADING_FOR_WAYPOINT_
 STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_VEL                        :{ORANGE}Heading for {DEPOT}, {VELOCITY}
 STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_SERVICE_VEL                :{LTBLUE}Service at {DEPOT}, {VELOCITY}
 
+STR_VEHICLE_STATUS_CANNOT_REACH_STATION_VEL                     :{LTBLUE}Cannot reach {STATION}, {VELOCITY}
+STR_VEHICLE_STATUS_CANNOT_REACH_WAYPOINT_VEL                    :{LTBLUE}Cannot reach {WAYPOINT}, {VELOCITY}
+STR_VEHICLE_STATUS_CANNOT_REACH_DEPOT_VEL                       :{ORANGE}Cannot reach {DEPOT}, {VELOCITY}
+STR_VEHICLE_STATUS_CANNOT_REACH_DEPOT_SERVICE_VEL               :{LTBLUE}Cannot reach {DEPOT}, {VELOCITY}
+
 # Vehicle stopped/started animations
 ###length 2
 STR_VEHICLE_COMMAND_STOPPED_SMALL                               :{TINY_FONT}{RED}Stopped
diff --git a/src/vehicle.cpp b/src/vehicle.cpp
--- a/src/vehicle.cpp
+++ b/src/vehicle.cpp
@@ -778,6 +778,8 @@ void Vehicle::HandlePathfindingResult(bo
 
 		/* Clear the flag as the PF's problem was solved. */
 		ClrBit(this->vehicle_flags, VF_PATHFINDER_LOST);
+		SetWindowWidgetDirty(WC_VEHICLE_VIEW, this->index, WID_VV_START_STOP);
+		InvalidateWindowClassesData(GetWindowClassForVehicleType(this->type));
 		/* Delete the news item. */
 		DeleteVehicleNews(this->index, STR_NEWS_VEHICLE_IS_LOST);
 		return;
@@ -788,6 +790,8 @@ void Vehicle::HandlePathfindingResult(bo
 
 	/* It is first time the problem occurred, set the "lost" flag. */
 	SetBit(this->vehicle_flags, VF_PATHFINDER_LOST);
+	SetWindowWidgetDirty(WC_VEHICLE_VIEW, this->index, WID_VV_START_STOP);
+	InvalidateWindowClassesData(GetWindowClassForVehicleType(this->type));
 	/* Notify user about the event. */
 	AI::NewEvent(this->owner, new ScriptEventVehicleLost(this->index));
 	if (_settings_client.gui.lost_vehicle_warn && this->owner == _local_company) {
diff --git a/src/vehicle_gui.cpp b/src/vehicle_gui.cpp
--- a/src/vehicle_gui.cpp
+++ b/src/vehicle_gui.cpp
@@ -1542,6 +1542,10 @@ void BaseVehicleListWindow::DrawVehicleL
 			case GB_NONE: {
 				const Vehicle *v = vehgroup.GetSingleVehicle();
 
+				if (HasBit(v->vehicle_flags, VF_PATHFINDER_LOST)) {
+					DrawSprite(SPR_WARNING_SIGN, PAL_NONE, vehicle_button_x, y + FONT_HEIGHT_NORMAL + 3 + GetSpriteSize(SPR_PROFIT_LOT).height);
+				}
+
 				DrawVehicleImage(v, image_left, image_right, y + FONT_HEIGHT_SMALL - 1, selected_vehicle, EIT_IN_LIST, 0);
 
 				if (!v->name.empty()) {
@@ -2732,7 +2736,7 @@ public:
 		const Vehicle *v = Vehicle::Get(this->window_number);
 		switch (widget) {
 			case WID_VV_START_STOP:
-				size->height = std::max(size->height, std::max(GetSpriteSize(SPR_FLAG_VEH_STOPPED).height, GetSpriteSize(SPR_FLAG_VEH_RUNNING).height) + WD_IMGBTN_TOP + WD_IMGBTN_BOTTOM);
+				size->height = std::max({size->height, GetSpriteSize(SPR_WARNING_SIGN).height, GetSpriteSize(SPR_FLAG_VEH_STOPPED).height, GetSpriteSize(SPR_FLAG_VEH_RUNNING).height}) + WD_IMGBTN_TOP + WD_IMGBTN_BOTTOM;
 				break;
 
 			case WID_VV_FORCE_PROCEED:
@@ -2821,7 +2825,7 @@ public:
 				case OT_GOTO_STATION: {
 					SetDParam(0, v->current_order.GetDestination());
 					SetDParam(1, v->GetDisplaySpeed());
-					str = STR_VEHICLE_STATUS_HEADING_FOR_STATION_VEL;
+					str = HasBit(v->vehicle_flags, VF_PATHFINDER_LOST) ? STR_VEHICLE_STATUS_CANNOT_REACH_STATION_VEL : STR_VEHICLE_STATUS_HEADING_FOR_STATION_VEL;
 					break;
 				}
 
@@ -2838,9 +2842,9 @@ public:
 						 * evaluating the string in the status bar. */
 						str = STR_EMPTY;
 					} else if (v->current_order.GetDepotActionType() & ODATFB_HALT) {
-						str = STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_VEL;
+						str = HasBit(v->vehicle_flags, VF_PATHFINDER_LOST) ? STR_VEHICLE_STATUS_CANNOT_REACH_DEPOT_VEL : STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_VEL;
 					} else {
-						str = STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_SERVICE_VEL;
+						str = HasBit(v->vehicle_flags, VF_PATHFINDER_LOST) ? STR_VEHICLE_STATUS_CANNOT_REACH_DEPOT_SERVICE_VEL : STR_VEHICLE_STATUS_HEADING_FOR_DEPOT_SERVICE_VEL;
 					}
 					break;
 				}
@@ -2852,7 +2856,7 @@ public:
 				case OT_GOTO_WAYPOINT: {
 					assert(v->type == VEH_TRAIN || v->type == VEH_SHIP);
 					SetDParam(0, v->current_order.GetDestination());
-					str = STR_VEHICLE_STATUS_HEADING_FOR_WAYPOINT_VEL;
+					str = HasBit(v->vehicle_flags, VF_PATHFINDER_LOST) ? STR_VEHICLE_STATUS_CANNOT_REACH_WAYPOINT_VEL : STR_VEHICLE_STATUS_HEADING_FOR_WAYPOINT_VEL;
 					SetDParam(1, v->GetDisplaySpeed());
 					break;
 				}
@@ -2876,12 +2880,12 @@ public:
 
 		/* Draw the flag plus orders. */
 		bool rtl = (_current_text_dir == TD_RTL);
-		uint text_offset = std::max(GetSpriteSize(SPR_FLAG_VEH_STOPPED).width, GetSpriteSize(SPR_FLAG_VEH_RUNNING).width) + WD_IMGBTN_LEFT + WD_IMGBTN_RIGHT;
+		uint text_offset = std::max({GetSpriteSize(SPR_WARNING_SIGN).width, GetSpriteSize(SPR_FLAG_VEH_STOPPED).width, GetSpriteSize(SPR_FLAG_VEH_RUNNING).width}) + WD_IMGBTN_LEFT + WD_IMGBTN_RIGHT;
 		int height = r.bottom - r.top;
 		int text_left = r.left + (rtl ? (uint)WD_FRAMERECT_LEFT : text_offset);
 		int text_right = r.right - (rtl ? text_offset : (uint)WD_FRAMERECT_RIGHT);
 		int text_top = r.top + WD_FRAMERECT_TOP + (height - WD_FRAMERECT_TOP - WD_FRAMERECT_BOTTOM - FONT_HEIGHT_NORMAL) / 2;
-		int image = ((v->vehstatus & VS_STOPPED) != 0) ? SPR_FLAG_VEH_STOPPED : SPR_FLAG_VEH_RUNNING;
+		int image = ((v->vehstatus & VS_STOPPED) != 0) ? SPR_FLAG_VEH_STOPPED : (HasBit(v->vehicle_flags, VF_PATHFINDER_LOST)) ? SPR_WARNING_SIGN : SPR_FLAG_VEH_RUNNING;
 		int image_left = (rtl ? text_right + 1 : r.left) + WD_IMGBTN_LEFT;
 		int image_top = r.top + WD_IMGBTN_TOP + (height - WD_IMGBTN_TOP + WD_IMGBTN_BOTTOM - GetSpriteSize(image).height) / 2;
 		int lowered = this->IsWidgetLowered(WID_VV_START_STOP) ? 1 : 0;