diff --git a/src/base_consist.cpp b/src/base_consist.cpp
index 69ad9c9d3e..3af6df77a4 100644
--- a/src/base_consist.cpp
+++ b/src/base_consist.cpp
@@ -41,6 +41,7 @@ void BaseConsist::CopyConsistPropertiesFrom(const BaseConsist *src)
 
 	this->cur_real_order_index = src->cur_real_order_index;
 	this->cur_implicit_order_index = src->cur_implicit_order_index;
+	this->cur_timetable_order_index = src->cur_timetable_order_index;
 
 	if (HasBit(src->vehicle_flags, VF_TIMETABLE_STARTED)) SetBit(this->vehicle_flags, VF_TIMETABLE_STARTED);
 	if (HasBit(src->vehicle_flags, VF_AUTOFILL_TIMETABLE)) SetBit(this->vehicle_flags, VF_AUTOFILL_TIMETABLE);
diff --git a/src/base_consist.h b/src/base_consist.h
index 6877539d9a..18bfd4b626 100644
--- a/src/base_consist.h
+++ b/src/base_consist.h
@@ -30,6 +30,7 @@ struct BaseConsist {
 
 	VehicleOrderID cur_real_order_index;///< The index to the current real (non-implicit) order
 	VehicleOrderID cur_implicit_order_index;///< The index to the current implicit order
+	VehicleOrderID cur_timetable_order_index;///< The index to the current real (non-implicit) order used for timetable updates
 
 	uint16 vehicle_flags;               ///< Used for gradual loading and other miscellaneous things (@see VehicleFlags enum)
 
diff --git a/src/departures.cpp b/src/departures.cpp
index 60e2f2fdb2..32c5dc4f4d 100644
--- a/src/departures.cpp
+++ b/src/departures.cpp
@@ -272,6 +272,13 @@ DepartureList* MakeDepartureList(StationID station, bool show_vehicle_types[5],
 
 			const Order *order = (*v)->GetOrder((*v)->cur_implicit_order_index % (*v)->GetNumOrders());
 			DateTicks start_date = date_fract_scaled - (*v)->current_order_time;
+			if ((*v)->cur_timetable_order_index != INVALID_VEH_ORDER_ID && (*v)->cur_timetable_order_index != (*v)->cur_real_order_index) {
+				/* vehicle is taking a conditional order branch, adjust start time to compensate */
+				const Order *real_current_order = (*v)->GetOrder((*v)->cur_real_order_index);
+				const Order *real_timetable_order = (*v)->GetOrder((*v)->cur_timetable_order_index);
+				assert(real_timetable_order->IsType(OT_CONDITIONAL));
+				start_date += (real_timetable_order->GetWaitTime() - real_current_order->GetTravelTime());
+			}
 			DepartureStatus status = D_TRAVELLING;
 			bool should_reset_lateness = false;
 			uint waiting_time = 0;
diff --git a/src/order_backup.cpp b/src/order_backup.cpp
index de0517cf71..4d0a3f6d64 100644
--- a/src/order_backup.cpp
+++ b/src/order_backup.cpp
@@ -89,6 +89,7 @@ void OrderBackup::DoRestore(Vehicle *v)
 	/* Make sure orders are in range */
 	v->UpdateRealOrderIndex();
 	if (v->cur_implicit_order_index >= v->GetNumOrders()) v->cur_implicit_order_index = v->cur_real_order_index;
+	if (v->cur_timetable_order_index >= v->GetNumOrders()) v->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 
 	/* Restore vehicle group */
 	DoCommand(0, this->group, v->index, DC_EXEC, CMD_ADD_VEHICLE_GROUP);
diff --git a/src/order_base.h b/src/order_base.h
index 5e911e8d7b..2ed546e567 100644
--- a/src/order_base.h
+++ b/src/order_base.h
@@ -32,6 +32,7 @@ extern OrderListPool _orderlist_pool;
 
 struct OrderExtraInfo {
 	uint8 cargo_type_flags[NUM_CARGO] = {}; ///< Load/unload types for each cargo type.
+	uint8 xflags = 0;                       ///< Extra flags
 };
 
 /* If you change this, keep in mind that it is saved on 3 places:
@@ -72,6 +73,17 @@ private:
 		if (!this->extra) this->AllocExtraInfo();
 	}
 
+	inline uint8 GetXFlags() const
+	{
+		return this->extra != nullptr ? this->extra->xflags : 0;
+	}
+
+	inline uint8 &GetXFlagsRef()
+	{
+		CheckExtraInfoAlloced();
+		return this->extra->xflags;
+	}
+
 public:
 	Order *next;          ///< Pointer to next order. If NULL, end of list
 
@@ -340,7 +352,7 @@ public:
 	 * explicitly set (but travel_time is actually unused for conditionals). */
 
 	/** Does this order have an explicit wait time set? */
-	inline bool IsWaitTimetabled() const { return this->IsType(OT_CONDITIONAL) ? this->wait_time > 0 : HasBit(this->flags, 3); }
+	inline bool IsWaitTimetabled() const { return this->IsType(OT_CONDITIONAL) ? HasBit(this->GetXFlags(), 0) : HasBit(this->flags, 3); }
 	/** Does this order have an explicit travel time set? */
 	inline bool IsTravelTimetabled() const { return this->IsType(OT_CONDITIONAL) ? this->travel_time > 0 : HasBit(this->flags, 7); }
 
@@ -361,7 +373,15 @@ public:
 	inline uint16 GetMaxSpeed() const { return this->max_speed; }
 
 	/** Set if the wait time is explicitly timetabled (unless the order is conditional). */
-	inline void SetWaitTimetabled(bool timetabled) { if (!this->IsType(OT_CONDITIONAL)) SB(this->flags, 3, 1, timetabled ? 1 : 0); }
+	inline void SetWaitTimetabled(bool timetabled)
+	{
+		if (this->IsType(OT_CONDITIONAL)) {
+			SB(this->GetXFlagsRef(), 0, 1, timetabled ? 1 : 0);
+		} else {
+			SB(this->flags, 3, 1, timetabled ? 1 : 0);
+		}
+	}
+
 	/** Set if the travel time is explicitly timetabled (unless the order is conditional). */
 	inline void SetTravelTimetabled(bool timetabled) { if (!this->IsType(OT_CONDITIONAL)) SB(this->flags, 7, 1, timetabled ? 1 : 0); }
 
@@ -494,7 +514,7 @@ private:
 
 	Ticks timetable_duration;         ///< NOSAVE: Total timetabled duration of the order list.
 	Ticks total_duration;             ///< NOSAVE: Total (timetabled or not) duration of the order list.
- 
+
 	std::vector<uint32> scheduled_dispatch;    ///< Scheduled dispatch time
 	uint32 scheduled_dispatch_duration;        ///< Scheduled dispatch duration
 	Date scheduled_dispatch_start_date;        ///< Scheduled dispatch start date
@@ -531,6 +551,8 @@ public:
 
 	Order *GetOrderAt(int index) const;
 
+	VehicleOrderID GetIndexOfOrder(const Order *order) const;
+
 	/**
 	 * Get the last order of the order chain.
 	 * @return the last order of the chain.
@@ -636,7 +658,7 @@ public:
 	 * @return  first scheduled dispatch
 	 */
 	inline const std::vector<uint32> &GetScheduledDispatch() { return this->scheduled_dispatch; }
-	
+
 	void AddScheduledDispatch(uint32 offset);
 	void RemoveScheduledDispatch(uint32 offset);
 	void UpdateScheduledDispatch();
diff --git a/src/order_cmd.cpp b/src/order_cmd.cpp
index 9152ad8be3..070fcaf7c4 100644
--- a/src/order_cmd.cpp
+++ b/src/order_cmd.cpp
@@ -375,8 +375,10 @@ void OrderList::Initialize(Order *chain, Vehicle *v)
 	for (Order *o = this->first; o != NULL; o = o->next) {
 		++this->num_orders;
 		if (!o->IsType(OT_IMPLICIT)) ++this->num_manual_orders;
-		this->timetable_duration += o->GetTimetabledWait() + o->GetTimetabledTravel();
-		this->total_duration += o->GetWaitTime() + o->GetTravelTime();
+		if (!o->IsType(OT_CONDITIONAL)) {
+			this->timetable_duration += o->GetTimetabledWait() + o->GetTimetabledTravel();
+			this->total_duration += o->GetWaitTime() + o->GetTravelTime();
+		}
 	}
 
 	for (Vehicle *u = this->first_shared->PreviousShared(); u != NULL; u = u->PreviousShared()) {
@@ -427,6 +429,24 @@ Order *OrderList::GetOrderAt(int index) const
 	return order;
 }
 
+/**
+ * Get the index of an order of the order chain, or INVALID_VEH_ORDER_ID.
+ * @param order order to get the index of.
+ * @return the position index of the given order, or INVALID_VEH_ORDER_ID.
+ */
+VehicleOrderID OrderList::GetIndexOfOrder(const Order *order) const
+{
+	VehicleOrderID index = 0;
+	const Order *o = this->first;
+	while (o != nullptr) {
+		if (o == order) return index;
+		index++;
+		o = o->next;
+	}
+
+	return INVALID_VEH_ORDER_ID;
+}
+
 /**
  * Get the next order which will make the given vehicle stop at a station
  * or refit at a depot or evaluate a non-trivial condition.
@@ -580,8 +600,10 @@ void OrderList::InsertOrderAt(Order *new_order, int index)
 	}
 	++this->num_orders;
 	if (!new_order->IsType(OT_IMPLICIT)) ++this->num_manual_orders;
-	this->timetable_duration += new_order->GetTimetabledWait() + new_order->GetTimetabledTravel();
-	this->total_duration += new_order->GetWaitTime() + new_order->GetTravelTime();
+	if (!new_order->IsType(OT_CONDITIONAL)) {
+		this->timetable_duration += new_order->GetTimetabledWait() + new_order->GetTimetabledTravel();
+		this->total_duration += new_order->GetWaitTime() + new_order->GetTravelTime();
+	}
 
 	/* We can visit oil rigs and buoys that are not our own. They will be shown in
 	 * the list of stations. So, we need to invalidate that window if needed. */
@@ -613,8 +635,10 @@ void OrderList::DeleteOrderAt(int index)
 	}
 	--this->num_orders;
 	if (!to_remove->IsType(OT_IMPLICIT)) --this->num_manual_orders;
-	this->timetable_duration -= (to_remove->GetTimetabledWait() + to_remove->GetTimetabledTravel());
-	this->total_duration -= (to_remove->GetWaitTime() + to_remove->GetTravelTime());
+	if (!to_remove->IsType(OT_CONDITIONAL)) {
+		this->timetable_duration -= (to_remove->GetTimetabledWait() + to_remove->GetTimetabledTravel());
+		this->total_duration -= (to_remove->GetWaitTime() + to_remove->GetTravelTime());
+	}
 	delete to_remove;
 }
 
@@ -716,8 +740,10 @@ void OrderList::DebugCheckSanity() const
 	for (const Order *o = this->first; o != NULL; o = o->next) {
 		++check_num_orders;
 		if (!o->IsType(OT_IMPLICIT)) ++check_num_manual_orders;
-		check_timetable_duration += o->GetTimetabledWait() + o->GetTimetabledTravel();
-		check_total_duration += o->GetWaitTime() + o->GetTravelTime();
+		if (!o->IsType(OT_CONDITIONAL)) {
+			check_timetable_duration += o->GetTimetabledWait() + o->GetTimetabledTravel();
+			check_total_duration += o->GetWaitTime() + o->GetTravelTime();
+		}
 	}
 	assert_msg(this->num_orders == check_num_orders, "%u, %u", this->num_orders, check_num_orders);
 	assert_msg(this->num_manual_orders == check_num_manual_orders, "%u, %u", this->num_manual_orders, check_num_manual_orders);
@@ -1103,6 +1129,13 @@ void InsertOrder(Vehicle *v, Order *new_o, VehicleOrderID sel_ord)
 				u->cur_implicit_order_index = cur;
 			}
 		}
+		if (sel_ord <= u->cur_timetable_order_index) {
+			uint cur = u->cur_timetable_order_index + 1;
+			/* Check if we don't go out of bound */
+			if (cur < u->GetNumOrders()) {
+				u->cur_timetable_order_index = cur;
+			}
+		}
 		/* Update any possible open window of the vehicle */
 		InvalidateVehicleOrder(u, INVALID_VEH_ORDER_ID | (sel_ord << 8));
 	}
@@ -1245,6 +1278,12 @@ void DeleteOrder(Vehicle *v, VehicleOrderID sel_ord)
 			}
 		}
 
+		if (sel_ord < u->cur_timetable_order_index) {
+			u->cur_timetable_order_index--;
+		} else if (sel_ord == u->cur_timetable_order_index) {
+			u->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
+		}
+
 		/* Update any possible open window of the vehicle */
 		InvalidateVehicleOrder(u, sel_ord | (INVALID_VEH_ORDER_ID << 8));
 	}
@@ -1296,6 +1335,7 @@ CommandCost CmdSkipToOrder(TileIndex tile, DoCommandFlag flags, uint32 p1, uint3
 
 		v->cur_implicit_order_index = v->cur_real_order_index = sel_ord;
 		v->UpdateRealOrderIndex();
+		v->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 
 		InvalidateVehicleOrder(v, VIWD_MODIFY_ORDERS);
 
@@ -1384,6 +1424,8 @@ CommandCost CmdMoveOrder(TileIndex tile, DoCommandFlag flags, uint32 p1, uint32
 				u->cur_implicit_order_index++;
 			}
 
+			u->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
+
 			assert(v->orders.list == u->orders.list);
 			/* Update any possible open window of the vehicle */
 			InvalidateVehicleOrder(u, moving_order | (target_order << 8));
@@ -2169,6 +2211,7 @@ void DeleteVehicleOrders(Vehicle *v, bool keep_orderlist, bool reset_order_indic
 
 	if (reset_order_indices) {
 		v->cur_implicit_order_index = v->cur_real_order_index = 0;
+		v->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 		if (v->current_order.IsType(OT_LOADING)) {
 			CancelLoadingDueToDeletedOrder(v);
 		}
@@ -2408,7 +2451,7 @@ bool UpdateOrderDest(Vehicle *v, const Order *order, int conditional_depth, bool
 				UpdateVehicleTimetable(v, false);
 				v->cur_implicit_order_index = v->cur_real_order_index = next_order;
 				v->UpdateRealOrderIndex();
-				v->current_order_time += v->GetOrder(v->cur_real_order_index)->GetTimetabledTravel();
+				v->cur_timetable_order_index = v->GetIndexOfOrder(order);
 
 				/* Disable creation of implicit orders.
 				 * When inserting them we do not know that we would have to make the conditional orders point to them. */
@@ -2417,6 +2460,7 @@ bool UpdateOrderDest(Vehicle *v, const Order *order, int conditional_depth, bool
 					SetBit(gv_flags, GVF_SUPPRESS_IMPLICIT_ORDERS);
 				}
 			} else {
+				v->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 				UpdateVehicleTimetable(v, true);
 				v->IncrementRealOrderIndex();
 			}
diff --git a/src/order_cmd.h b/src/order_cmd.h
index bbb6c1dc59..a463899460 100644
--- a/src/order_cmd.h
+++ b/src/order_cmd.h
@@ -42,9 +42,9 @@ restart:
 			}
 
 			/* Clear wait time */
-			v->orders.list->UpdateTotalDuration(-order->GetWaitTime());
+			if (!order->IsType(OT_CONDITIONAL)) v->orders.list->UpdateTotalDuration(-order->GetWaitTime());
 			if (order->IsWaitTimetabled()) {
-				v->orders.list->UpdateTimetableDuration(-order->GetTimetabledWait());
+				if (!order->IsType(OT_CONDITIONAL)) v->orders.list->UpdateTimetableDuration(-order->GetTimetabledWait());
 				order->SetWaitTimetabled(false);
 			}
 			order->SetWaitTime(0);
diff --git a/src/saveload/afterload.cpp b/src/saveload/afterload.cpp
index b2ce60b052..c05d22439a 100644
--- a/src/saveload/afterload.cpp
+++ b/src/saveload/afterload.cpp
@@ -3415,6 +3415,27 @@ bool AfterLoadGame()
 		}
 	}
 
+	if (SlXvIsFeatureMissing(XSLFI_TIMETABLE_EXTRA)) {
+		Vehicle *v;
+		FOR_ALL_VEHICLES(v) {
+			v->cur_timetable_order_index = v->GetNumManualOrders() > 0 ? v->cur_real_order_index : INVALID_VEH_ORDER_ID;
+		}
+		OrderBackup *bckup;
+		FOR_ALL_ORDER_BACKUPS(bckup) {
+			bckup->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
+		}
+		Order *order;
+		FOR_ALL_ORDERS(order) {
+			if (order->IsType(OT_CONDITIONAL)) {
+				assert(order->GetTravelTime() == 0);
+			}
+		}
+		OrderList *order_list;
+		FOR_ALL_ORDER_LISTS(order_list) {
+			order_list->DebugCheckSanity();
+		}
+	}
+
 	/* Road stops is 'only' updating some caches */
 	AfterLoadRoadStops();
 	AfterLoadLabelMaps();
diff --git a/src/saveload/extended_ver_sl.cpp b/src/saveload/extended_ver_sl.cpp
index a0861ab7a1..d6c3bc7c0b 100644
--- a/src/saveload/extended_ver_sl.cpp
+++ b/src/saveload/extended_ver_sl.cpp
@@ -79,6 +79,7 @@ const SlxiSubChunkInfo _sl_xv_sub_chunk_infos[] = {
 	{ XSLFI_SCHEDULED_DISPATCH,     XSCF_NULL,                1,   1, "scheduled_dispatch",        NULL, NULL, NULL        },
 	{ XSLFI_MORE_TOWN_GROWTH_RATES, XSCF_NULL,                1,   1, "more_town_growth_rates",    NULL, NULL, NULL        },
 	{ XSLFI_MULTIPLE_DOCKS,         XSCF_NULL,                1,   1, "multiple_docks",            NULL, NULL, "DOCK"      },
+	{ XSLFI_TIMETABLE_EXTRA,        XSCF_NULL,                1,   1, "timetable_extra",           NULL, NULL, "ORDX"      },
 	{ XSLFI_NULL, XSCF_NULL, 0, 0, NULL, NULL, NULL, NULL },// This is the end marker
 };
 
diff --git a/src/saveload/extended_ver_sl.h b/src/saveload/extended_ver_sl.h
index 89c84fe346..0a6cef1b0d 100644
--- a/src/saveload/extended_ver_sl.h
+++ b/src/saveload/extended_ver_sl.h
@@ -53,6 +53,7 @@ enum SlXvFeatureIndex {
 	XSLFI_SCHEDULED_DISPATCH,                     ///< Scheduled vehicle dispatching
 	XSLFI_MORE_TOWN_GROWTH_RATES,                 ///< More town growth rates
 	XSLFI_MULTIPLE_DOCKS,                         ///< Multiple docks
+	XSLFI_TIMETABLE_EXTRA,                        ///< Vehicle timetable extra fields
 
 	XSLFI_RIFF_HEADER_60_BIT,                     ///< Size field in RIFF chunk header is 60 bit
 	XSLFI_HEIGHT_8_BIT,                           ///< Map tile height is 8 bit instead of 4 bit, but savegame version may be before this became true in trunk
diff --git a/src/saveload/order_sl.cpp b/src/saveload/order_sl.cpp
index 76d609d55d..53926a9a92 100644
--- a/src/saveload/order_sl.cpp
+++ b/src/saveload/order_sl.cpp
@@ -192,6 +192,8 @@ static void Load_ORDR()
 			if (IsSavegameVersionBefore(190)) {
 				order->SetTravelTimetabled(order->GetTravelTime() > 0);
 				order->SetWaitTimetabled(order->GetWaitTime() > 0);
+			} else if (order->IsType(OT_CONDITIONAL) && SlXvIsFeatureMissing(XSLFI_TIMETABLE_EXTRA)) {
+				order->SetWaitTimetabled(order->GetWaitTime() > 0);
 			}
 		}
 	}
@@ -201,6 +203,7 @@ const SaveLoad *GetOrderExtraInfoDescription()
 {
 	static const SaveLoad _order_extra_info_desc[] = {
 		SLE_ARR(OrderExtraInfo, cargo_type_flags, SLE_UINT8, NUM_CARGO),
+		SLE_CONDVAR_X(OrderExtraInfo, xflags, SLE_UINT8, 0, SL_MAX_VERSION, SlXvFeatureTest(XSLFTO_AND, XSLFI_TIMETABLE_EXTRA)),
 		SLE_END()
 	};
 
@@ -302,6 +305,7 @@ const SaveLoad *GetOrderBackupDescription()
 		 SLE_CONDREF(OrderBackup, clone,                    REF_VEHICLE,               192, SL_MAX_VERSION),
 		     SLE_VAR(OrderBackup, cur_real_order_index,     SLE_UINT8),
 		 SLE_CONDVAR(OrderBackup, cur_implicit_order_index, SLE_UINT8,                 176, SL_MAX_VERSION),
+		SLE_CONDVAR_X(OrderBackup, cur_timetable_order_index, SLE_UINT8,                 0, SL_MAX_VERSION, SlXvFeatureTest(XSLFTO_AND, XSLFI_TIMETABLE_EXTRA)),
 		 SLE_CONDVAR(OrderBackup, current_order_time,       SLE_UINT32,                176, SL_MAX_VERSION),
 		 SLE_CONDVAR(OrderBackup, lateness_counter,         SLE_INT32,                 176, SL_MAX_VERSION),
 		 SLE_CONDVAR(OrderBackup, timetable_start,          SLE_INT32,                 176, SL_MAX_VERSION),
diff --git a/src/saveload/vehicle_sl.cpp b/src/saveload/vehicle_sl.cpp
index c12fb5bb78..0aa6c24b74 100644
--- a/src/saveload/vehicle_sl.cpp
+++ b/src/saveload/vehicle_sl.cpp
@@ -632,6 +632,7 @@ const SaveLoad *GetVehicleDescription(VehicleType vt)
 
 		     SLE_VAR(Vehicle, cur_implicit_order_index,  SLE_UINT8),
 		 SLE_CONDVAR(Vehicle, cur_real_order_index,  SLE_UINT8,                  158, SL_MAX_VERSION),
+		SLE_CONDVAR_X(Vehicle, cur_timetable_order_index, SLE_UINT8,               0, SL_MAX_VERSION, SlXvFeatureTest(XSLFTO_AND, XSLFI_TIMETABLE_EXTRA)),
 		/* num_orders is now part of OrderList and is not saved but counted */
 		SLE_CONDNULL(1,                                                            0, 104),
 
diff --git a/src/timetable_cmd.cpp b/src/timetable_cmd.cpp
index 5f6ec72260..5e4045b3db 100644
--- a/src/timetable_cmd.cpp
+++ b/src/timetable_cmd.cpp
@@ -21,6 +21,7 @@
 #include "company_base.h"
 #include "core/sort_func.hpp"
 #include "settings_type.h"
+#include "scope.h"
 
 #include "table/strings.h"
 
@@ -42,15 +43,20 @@ static void ChangeTimetable(Vehicle *v, VehicleOrderID order_number, uint16 val,
 
 	switch (mtf) {
 		case MTF_WAIT_TIME:
-			total_delta = val - order->GetWaitTime();
-			timetable_delta = (timetabled ? val : 0) - order->GetTimetabledWait();
+			if (!order->IsType(OT_CONDITIONAL)) {
+				total_delta = val - order->GetWaitTime();
+				timetable_delta = (timetabled ? val : 0) - order->GetTimetabledWait();
+			}
 			order->SetWaitTime(val);
 			order->SetWaitTimetabled(timetabled);
 			break;
 
 		case MTF_TRAVEL_TIME:
-			total_delta = val - order->GetTravelTime();
-			timetable_delta = (timetabled ? val : 0) - order->GetTimetabledTravel();
+			if (!order->IsType(OT_CONDITIONAL)) {
+				total_delta = val - order->GetTravelTime();
+				timetable_delta = (timetabled ? val : 0) - order->GetTimetabledTravel();
+			}
+			if (order->IsType(OT_CONDITIONAL)) assert_msg(val == order->GetTravelTime(), "%u == %u", val, order->GetTravelTime());
 			order->SetTravelTime(val);
 			order->SetTravelTimetabled(timetabled);
 			break;
@@ -714,6 +720,12 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 	if (v->cur_real_order_index >= v->GetNumOrders()) return;
 	Order *real_current_order = v->GetOrder(v->cur_real_order_index);
+	Order *real_timetable_order = v->cur_timetable_order_index != INVALID_VEH_ORDER_ID ? v->GetOrder(v->cur_timetable_order_index) : nullptr;
+
+	auto guard = scope_guard([v, travelling]() {
+		/* On next call, when updating waiting time, use current order even if travel field of current order isn't being updated */
+		if (travelling) v->cur_timetable_order_index = v->cur_real_order_index;
+	});
 
 	VehicleOrderID first_manual_order = 0;
 	for (Order *o = v->GetFirstOrder(); o != NULL && o->IsType(OT_IMPLICIT); o = o->next) {
@@ -768,10 +780,12 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 	}
 
 	if (!HasBit(v->vehicle_flags, VF_TIMETABLE_STARTED)) return;
+	if (real_timetable_order == nullptr) return;
 
 	bool autofilling = HasBit(v->vehicle_flags, VF_AUTOFILL_TIMETABLE);
-	bool remeasure_wait_time = !real_current_order->IsWaitTimetabled() ||
-			(autofilling && !HasBit(v->vehicle_flags, VF_AUTOFILL_PRES_WAIT_TIME));
+	bool is_conditional = real_timetable_order->IsType(OT_CONDITIONAL);
+	bool remeasure_wait_time = !is_conditional && (!real_timetable_order->IsWaitTimetabled() ||
+			(autofilling && !HasBit(v->vehicle_flags, VF_AUTOFILL_PRES_WAIT_TIME)));
 
 	if (travelling && remeasure_wait_time) {
 		/* We just finished travelling and want to remeasure the loading time,
@@ -779,11 +793,23 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 		v->current_order.SetWaitTime(0);
 	}
 
+	bool travel_field = travelling;
+	if (is_conditional) {
+		if (travelling) {
+			/* conditional orders use the wait field for the jump-taken travel time */
+			travel_field = false;
+		} else {
+			/* doesn't make sense to update wait time for conditional orders */
+			return;
+		}
+	} else {
+		assert(real_timetable_order == real_current_order);
+	}
+
 	if (just_started) return;
 
 	/* Before modifying waiting times, check whether we want to preserve bigger ones. */
-	if (!real_current_order->IsType(OT_CONDITIONAL) &&
-			(travelling || time_taken > real_current_order->GetWaitTime() || remeasure_wait_time)) {
+	if ((travelling || time_taken > real_timetable_order->GetWaitTime() || remeasure_wait_time)) {
 		/* Round the time taken up to the nearest timetable rounding factor
 		 * (default: day), as this will avoid confusion for people who are
 		 * timetabling in days, and can be adjusted later by people who aren't.
@@ -797,10 +823,10 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 		uint rounding_factor = owner ? owner->settings.timetable_autofill_rounding : DAY_TICKS;
 		uint time_to_set = CeilDiv(max(time_taken, 1U), rounding_factor) * rounding_factor;
 
-		if (travelling && (autofilling || !real_current_order->IsTravelTimetabled())) {
-			ChangeTimetable(v, v->cur_real_order_index, time_to_set, MTF_TRAVEL_TIME, autofilling);
-		} else if (!travelling && (autofilling || !real_current_order->IsWaitTimetabled())) {
-			ChangeTimetable(v, v->cur_real_order_index, time_to_set, MTF_WAIT_TIME, autofilling);
+		if (travel_field && (autofilling || !real_timetable_order->IsTravelTimetabled())) {
+			ChangeTimetable(v, v->cur_timetable_order_index, time_to_set, MTF_TRAVEL_TIME, autofilling);
+		} else if (!travel_field && (autofilling || !real_timetable_order->IsWaitTimetabled())) {
+			ChangeTimetable(v, v->cur_timetable_order_index, time_to_set, MTF_WAIT_TIME, autofilling);
 		}
 	}
 
@@ -814,8 +840,8 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 	if (autofilling) return;
 
-	uint timetabled = travelling ? real_current_order->GetTimetabledTravel() :
-			real_current_order->GetTimetabledWait();
+	uint timetabled = travel_field ? real_timetable_order->GetTimetabledTravel() :
+			real_timetable_order->GetTimetabledWait();
 
 	/* Update the timetable to gradually shift order times towards the actual travel times. */
 	if (timetabled != 0 && HasBit(v->vehicle_flags, VF_AUTOMATE_TIMETABLE)) {
@@ -829,7 +855,7 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 		if (new_time > (int32)timetabled * 4 && travelling) {
 			/* Possible jam, clear time and restart timetable for all vehicles.
 			 * Otherwise we risk trains blocking 1-lane stations for long times. */
-			ChangeTimetable(v, v->cur_real_order_index, 0, travelling ? MTF_TRAVEL_TIME : MTF_WAIT_TIME, true);
+			ChangeTimetable(v, v->cur_timetable_order_index, 0, travel_field ? MTF_TRAVEL_TIME : MTF_WAIT_TIME, true);
 			for (Vehicle *v2 = v->FirstShared(); v2 != NULL; v2 = v2->NextShared()) {
 				v2->ClearSeparation();
 				ClrBit(v2->vehicle_flags, VF_TIMETABLE_STARTED);
@@ -849,14 +875,15 @@ void UpdateVehicleTimetable(Vehicle *v, bool travelling)
 
 		if (new_time < 1) new_time = 1;
 		if (new_time != (int32)timetabled) {
-			ChangeTimetable(v, v->cur_real_order_index, new_time, travelling ? MTF_TRAVEL_TIME : MTF_WAIT_TIME, true);
+			ChangeTimetable(v, v->cur_timetable_order_index, new_time, travel_field ? MTF_TRAVEL_TIME : MTF_WAIT_TIME, true);
 		}
 	} else if (timetabled == 0 && HasBit(v->vehicle_flags, VF_AUTOMATE_TIMETABLE)) {
 		/* Add times for orders that are not yet timetabled, even while not autofilling */
-		if (travelling) {
-			ChangeTimetable(v, v->cur_real_order_index, time_taken, MTF_TRAVEL_TIME, true);
+		const int32 new_time = travelling ? time_taken : time_loading;
+		if (travel_field) {
+			ChangeTimetable(v, v->cur_timetable_order_index, new_time, MTF_TRAVEL_TIME, true);
 		} else {
-			ChangeTimetable(v, v->cur_real_order_index, time_loading, MTF_WAIT_TIME, true);
+			ChangeTimetable(v, v->cur_timetable_order_index, new_time, MTF_WAIT_TIME, true);
 		}
 	}
 
diff --git a/src/timetable_gui.cpp b/src/timetable_gui.cpp
index 3f0398332a..65b8b50a49 100644
--- a/src/timetable_gui.cpp
+++ b/src/timetable_gui.cpp
@@ -217,6 +217,13 @@ struct TimetableWindow : Window {
 
 		bool travelling = (!(v->current_order.IsType(OT_LOADING) || v->current_order.IsType(OT_WAITING)) || v->current_order.GetNonStopType() == ONSF_STOP_EVERYWHERE);
 		Ticks start_time = -v->current_order_time;
+		if (v->cur_timetable_order_index != INVALID_VEH_ORDER_ID && v->cur_timetable_order_index != v->cur_real_order_index) {
+			/* vehicle is taking a conditional order branch, adjust start time to compensate */
+			const Order *real_current_order = v->GetOrder(v->cur_real_order_index);
+			const Order *real_timetable_order = v->GetOrder(v->cur_timetable_order_index);
+			assert(real_timetable_order->IsType(OT_CONDITIONAL));
+			start_time += (real_timetable_order->GetWaitTime() - real_current_order->GetTravelTime());
+		}
 
 		FillTimetableArrivalDepartureTable(v, v->cur_real_order_index % v->GetNumOrders(), travelling, table, start_time);
 
diff --git a/src/vehicle.cpp b/src/vehicle.cpp
index 517a98879e..193bb0698c 100644
--- a/src/vehicle.cpp
+++ b/src/vehicle.cpp
@@ -2892,6 +2892,9 @@ CommandCost Vehicle::SendToDepot(DoCommandFlag flags, DepotCommand command, Tile
 				this->current_order.MakeDummy();
 				SetWindowWidgetDirty(WC_VEHICLE_VIEW, this->index, WID_VV_START_STOP);
 			}
+
+			/* prevent any attempt to update timetable for current order, as actual travel time will be incorrect due to depot command */
+			this->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 		}
 		return CommandCost();
 	}
diff --git a/src/vehicle_base.h b/src/vehicle_base.h
index 3829a5d850..bb78e496ad 100644
--- a/src/vehicle_base.h
+++ b/src/vehicle_base.h
@@ -855,8 +855,10 @@ private:
 				this->cur_real_order_index++;
 				if (this->cur_real_order_index >= this->GetNumOrders()) this->cur_real_order_index = 0;
 			} while (this->GetOrder(this->cur_real_order_index)->IsType(OT_IMPLICIT));
+			this->cur_timetable_order_index = this->cur_real_order_index;
 		} else {
 			this->cur_real_order_index = 0;
+			this->cur_timetable_order_index = INVALID_VEH_ORDER_ID;
 		}
 	}
 
@@ -931,6 +933,16 @@ public:
 		return (this->orders.list == NULL) ? NULL : this->orders.list->GetOrderAt(index);
 	}
 
+	/**
+	 * Get the index of an order of the order chain, or INVALID_VEH_ORDER_ID.
+	 * @param order order to get the index of.
+	 * @return the position index of the given order, or INVALID_VEH_ORDER_ID.
+	 */
+	inline VehicleOrderID GetIndexOfOrder(const Order *order) const
+	{
+		return (this->orders.list == NULL) ? INVALID_VEH_ORDER_ID : this->orders.list->GetIndexOfOrder(order);
+	}
+
 	/**
 	 * Returns the last order of a vehicle, or NULL if it doesn't exists
 	 * @return last order of a vehicle, if available