diff --git a/src/command.cpp b/src/command.cpp
index 3aa93777c5..9c0a714eec 100644
--- a/src/command.cpp
+++ b/src/command.cpp
@@ -179,6 +179,7 @@ DEF_COMMAND(CmdSetGroupReplaceProtection);
 DEF_COMMAND(CmdMoveOrder);
 DEF_COMMAND(CmdChangeTimetable);
 DEF_COMMAND(CmdSetVehicleOnTime);
+DEF_COMMAND(CmdAutofillTimetable);
 
 /* The master command table */
 static const Command _command_proc_table[] = {
@@ -335,6 +336,7 @@ static const Command _command_proc_table[] = {
 	{CmdMoveOrder,                           0}, /* 127 */
 	{CmdChangeTimetable,                     0}, /* 128 */
 	{CmdSetVehicleOnTime,                    0}, /* 129 */
+	{CmdAutofillTimetable,                   0}, /* 130 */
 };
 
 /* This function range-checks a cmd, and checks if the cmd is not NULL */
diff --git a/src/command.h b/src/command.h
index c19027a310..8cb78c9e06 100644
--- a/src/command.h
+++ b/src/command.h
@@ -155,6 +155,7 @@ enum {
 	CMD_MOVE_ORDER                   = 127,
 	CMD_CHANGE_TIMETABLE             = 128,
 	CMD_SET_VEHICLE_ON_TIME          = 129,
+	CMD_AUTOFILL_TIMETABLE           = 130,
 };
 
 enum {
diff --git a/src/lang/english.txt b/src/lang/english.txt
index 63849c6998..0bb5536cd7 100644
--- a/src/lang/english.txt
+++ b/src/lang/english.txt
@@ -2773,6 +2773,8 @@ STR_TIMETABLE_CHANGE_TIME                                       :{BLACK}Change T
 STR_TIMETABLE_STATUS_ON_TIME                                    :This vehicle is currently running on time
 STR_TIMETABLE_STATUS_LATE                                       :This vehicle is currently running {STRING1} late
 STR_TIMETABLE_STATUS_EARLY                                      :This vehicle is currently running {STRING1} early
+STR_TIMETABLE_AUTOFILL                                          :{BLACK}Autofill
+STR_TIMETABLE_AUTOFILL_TOOLTIP                                  :{BLACK}Fill the timetable automatically with the values from the first journey
 
 ##id 0x9000
 STR_9000_ROAD_VEHICLE_IN_THE_WAY                                :{WHITE}Road vehicle in the way
diff --git a/src/timetable_cmd.cpp b/src/timetable_cmd.cpp
index ee333cb785..1012212168 100644
--- a/src/timetable_cmd.cpp
+++ b/src/timetable_cmd.cpp
@@ -8,9 +8,32 @@
 #include "variables.h"
 #include "table/strings.h"
 #include "command.h"
+#include "date.h"
+#include "player.h"
 #include "vehicle.h"
 
 
+static void ChangeTimetable(Vehicle *v, VehicleOrderID order_number, uint16 time, bool is_journey)
+{
+	Order *order = GetVehicleOrder(v, order_number);
+
+	if (is_journey) {
+		order->travel_time = time;
+	} else {
+		order->wait_time = time;
+	}
+
+	if (v->cur_order_index == order_number && HASBIT(v->current_order.flags, OFB_PART_OF_ORDERS)) {
+		if (is_journey) {
+			v->current_order.travel_time = time;
+		} else {
+			v->current_order.wait_time = time;
+		}
+	}
+
+	InvalidateWindow(WC_VEHICLE_TIMETABLE, v->index);
+}
+
 /**
  * Add or remove waiting times from an order.
  * @param tile Not used.
@@ -43,21 +66,7 @@ CommandCost CmdChangeTimetable(TileIndex tile, uint32 flags, uint32 p1, uint32 p
 	}
 
 	if (flags & DC_EXEC) {
-		if (is_journey) {
-			order->travel_time = p2;
-		} else {
-			order->wait_time = p2;
-		}
-
-		if (v->cur_order_index == order_number && HASBIT(v->current_order.flags, OFB_PART_OF_ORDERS)) {
-			if (is_journey) {
-				v->current_order.travel_time = p2;
-			} else {
-				v->current_order.wait_time = p2;
-			}
-		}
-
-		InvalidateWindow(WC_VEHICLE_TIMETABLE, v->index);
+		ChangeTimetable(v, order_number, p2, is_journey);
 	}
 
 	return CommandCost();
@@ -87,6 +96,46 @@ CommandCost CmdSetVehicleOnTime(TileIndex tile, uint32 flags, uint32 p1, uint32
 	return CommandCost();
 }
 
+/**
+ * Start or stop filling the timetable automatically from the time the vehicle
+ * actually takes to complete it. When starting to autofill the current times
+ * are cleared and the timetable will start again from scratch.
+ * @param tile Not used.
+ * @param flags Operation to perform.
+ * @param p1 Vehicle index.
+ * @param p2 Set to 1 to enable, 0 to disable.
+ */
+CommandCost CmdAutofillTimetable(TileIndex tile, uint32 flags, uint32 p1, uint32 p2)
+{
+	if (!_patches.timetabling) return CMD_ERROR;
+
+	VehicleID veh = GB(p1, 0, 16);
+	if (!IsValidVehicleID(veh)) return CMD_ERROR;
+
+	Vehicle *v = GetVehicle(veh);
+	if (!CheckOwnership(v->owner)) return CMD_ERROR;
+
+	if (flags & DC_EXEC) {
+		if (p2 == 1) {
+			/* Start autofilling the timetable, which clears all the current
+			 * timings and clears the "timetable has started" bit. */
+			SETBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE);
+			CLRBIT(v->vehicle_flags, VF_TIMETABLE_STARTED);
+
+			for (Order *order = GetVehicleOrder(v, 0); order != NULL; order = order->next) {
+				order->wait_time = 0;
+				order->travel_time = 0;
+			}
+
+			v->current_order.wait_time = 0;
+			v->current_order.travel_time = 0;
+		} else {
+			CLRBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE);
+		}
+	}
+
+	return CommandCost();
+}
 
 void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 {
@@ -95,10 +144,37 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 	v->current_order_time = 0;
 
+	if (!_patches.timetabling) return;
+
+	/* Make sure the timetable only starts when the vehicle reaches the first
+ 	 * order, not when travelling from the depot to the first station. */
+ 	if (v->cur_order_index == 0 && !HASBIT(v->vehicle_flags, VF_TIMETABLE_STARTED)) {
+ 		SETBIT(v->vehicle_flags, VF_TIMETABLE_STARTED);
+ 		return;
+ 	}
+
+	if (!HASBIT(v->vehicle_flags, VF_TIMETABLE_STARTED)) return;
+
+ 	if (HASBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE)) {
+		if (timetabled == 0) {
+			/* Round the time taken up to the nearest day, as this will avoid
+			 * confusion for people who are timetabling in days, and can be
+			 * adjusted later by people who aren't. */
+			time_taken = (((time_taken - 1) / DAY_TICKS) + 1) * DAY_TICKS;
+
+			ChangeTimetable(v, v->cur_order_index, time_taken, travelling);
+			return;
+		} else if (v->cur_order_index == 0) {
+			/* Otherwise if we're at the beginning and it already has a value,
+			 * assume that autofill is finished and turn it off again. */
+			CLRBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE);
+		}
+ 	}
+
 	/* Vehicles will wait at stations if they arrive early even if they are not
 	 * timetabled to wait there, so make sure the lateness counter is updated
 	 * when this happens. */
-	if (!_patches.timetabling || (timetabled == 0 && (travelling || v->lateness_counter >= 0))) return;
+	if (timetabled == 0 && (travelling || v->lateness_counter >= 0)) return;
 
 	v->lateness_counter -= (timetabled - time_taken);
 
diff --git a/src/timetable_gui.cpp b/src/timetable_gui.cpp
index 891f8f0eb4..699084d948 100644
--- a/src/timetable_gui.cpp
+++ b/src/timetable_gui.cpp
@@ -67,12 +67,16 @@ static void DrawTimetableWindow(Window *w)
 		}
 
 		EnableWindowWidget(w, 8);
+		EnableWindowWidget(w, 9);
 	} else {
 		DisableWindowWidget(w, 6);
 		DisableWindowWidget(w, 7);
 		DisableWindowWidget(w, 8);
+		DisableWindowWidget(w, 9);
 	}
 
+	SetWindowWidgetLoweredState(w, 9, HASBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE));
+
 	SetDParam(0, v->index);
 	DrawWindowWidgets(w);
 
@@ -242,6 +246,10 @@ static void TimetableWndProc(Window *w, WindowEvent *we)
 				case 8: /* Reset the vehicle's late counter. */
 					DoCommandP(0, v->index, 0, NULL, CMD_SET_VEHICLE_ON_TIME | CMD_MSG(STR_CAN_T_TIMETABLE_VEHICLE));
 					break;
+
+				case 9: /* Autofill the timetable. */
+					DoCommandP(0, v->index, HASBIT(v->vehicle_flags, VF_AUTOFILL_TIMETABLE) ? 0 : 1, NULL, CMD_AUTOFILL_TIMETABLE | CMD_MSG(STR_CAN_T_TIMETABLE_VEHICLE));
+					break;
 			}
 
 			SetWindowDirty(w);
@@ -270,26 +278,27 @@ static void TimetableWndProc(Window *w, WindowEvent *we)
 
 static const Widget _timetable_widgets[] = {
 	{   WWT_CLOSEBOX,   RESIZE_NONE,    14,     0,    10,     0,    13, STR_00C5,                   STR_018B_CLOSE_WINDOW},
-	{    WWT_CAPTION,   RESIZE_RIGHT,   14,    11,   337,     0,    13, STR_TIMETABLE_TITLE,        STR_018C_WINDOW_TITLE_DRAG_THIS},
-	{  WWT_STICKYBOX,   RESIZE_LR,      14,   338,   349,     0,    13, STR_NULL,                   STR_STICKY_BUTTON},
+	{    WWT_CAPTION,   RESIZE_RIGHT,   14,    11,   387,     0,    13, STR_TIMETABLE_TITLE,        STR_018C_WINDOW_TITLE_DRAG_THIS},
+	{  WWT_STICKYBOX,   RESIZE_LR,      14,   388,   399,     0,    13, STR_NULL,                   STR_STICKY_BUTTON},
 
-	{      WWT_PANEL,   RESIZE_RB,      14,     0,   337,    14,    95, STR_NULL,                   STR_TIMETABLE_TOOLTIP},
-	{  WWT_SCROLLBAR,   RESIZE_LRB,     14,   338,   349,    14,    95, STR_NULL,                   STR_0190_SCROLL_BAR_SCROLLS_LIST},
+	{      WWT_PANEL,   RESIZE_RB,      14,     0,   387,    14,    95, STR_NULL,                   STR_TIMETABLE_TOOLTIP},
+	{  WWT_SCROLLBAR,   RESIZE_LRB,     14,   388,   399,    14,    95, STR_NULL,                   STR_0190_SCROLL_BAR_SCROLLS_LIST},
 
-	{      WWT_PANEL,   RESIZE_RTB,     14,     0,   349,    96,   107, STR_NULL,                   STR_NULL},
+	{      WWT_PANEL,   RESIZE_RTB,     14,     0,   399,    96,   107, STR_NULL,                   STR_NULL},
 
 	{ WWT_PUSHTXTBTN,   RESIZE_TB,      14,     0,   109,   108,   119, STR_TIMETABLE_CHANGE_TIME,  STR_TIMETABLE_WAIT_TIME_TOOLTIP},
 	{ WWT_PUSHTXTBTN,   RESIZE_TB,      14,   110,   219,   108,   119, STR_CLEAR_TIME,             STR_TIMETABLE_CLEAR_TIME_TOOLTIP},
 	{ WWT_PUSHTXTBTN,   RESIZE_TB,      14,   220,   337,   108,   119, STR_RESET_LATENESS,         STR_TIMETABLE_RESET_LATENESS_TOOLTIP},
+	{ WWT_PUSHTXTBTN,   RESIZE_TB,      14,   338,   387,   108,   119, STR_TIMETABLE_AUTOFILL,     STR_TIMETABLE_AUTOFILL_TOOLTIP},
 
-	{      WWT_PANEL,   RESIZE_RTB,     14,   338,   337,   108,   119, STR_NULL,                   STR_NULL},
-	{  WWT_RESIZEBOX,   RESIZE_LRTB,    14,   338,   349,   108,   119, STR_NULL,                   STR_RESIZE_BUTTON},
+	{      WWT_PANEL,   RESIZE_RTB,     14,   388,   387,   108,   119, STR_NULL,                   STR_NULL},
+	{  WWT_RESIZEBOX,   RESIZE_LRTB,    14,   388,   399,   108,   119, STR_NULL,                   STR_RESIZE_BUTTON},
 
 	{    WIDGETS_END }
 };
 
 static const WindowDesc _timetable_desc = {
-	WDP_AUTO, WDP_AUTO, 350, 120,
+	WDP_AUTO, WDP_AUTO, 400, 120,
 	WC_VEHICLE_TIMETABLE, WC_VEHICLE_VIEW,
 	WDF_STD_TOOLTIPS | WDF_STD_BTN | WDF_DEF_WIDGET | WDF_UNCLICK_BUTTONS | WDF_STICKY_BUTTON | WDF_RESIZABLE,
 	_timetable_widgets,
diff --git a/src/vehicle.h b/src/vehicle.h
index d8f039de11..7b2b5cebc4 100644
--- a/src/vehicle.h
+++ b/src/vehicle.h
@@ -95,6 +95,8 @@ enum VehicleFlags {
 	VF_LOADING_FINISHED,
 	VF_CARGO_UNLOADING,
 	VF_BUILT_AS_PROTOTYPE,
+	VF_TIMETABLE_STARTED,  ///< Whether the vehicle has started running on the timetable yet.
+	VF_AUTOFILL_TIMETABLE, ///< Whether the vehicle should fill in the timetable automatically.
 };
 
 /* Effect vehicle types */