diff --git a/src/lang/english.txt b/src/lang/english.txt
index b91eaf8c20..1e9ce36b9d 100644
--- a/src/lang/english.txt
+++ b/src/lang/english.txt
@@ -4650,6 +4650,8 @@ STR_TIMETABLE_AUTOSEP_SINGLE_VEH                                :{BLACK}This tim
 STR_TIMETABLE_WARNING_AUTOSEP_CONDITIONAL                       :{BLACK}Cannot auto separate timetable: conditional order(s) present
 STR_TIMETABLE_WARNING_AUTOSEP_MISSING_TIMINGS                   :{BLACK}Cannot auto separate timetable: wait or travel time(s) missing
 STR_TIMETABLE_WARNING_FULL_LOAD                                 :{BLACK}Timetabling full-load orders is not recommended
+STR_TIMETABLE_WARNING_AUTOFILL_CONDITIONAL                      :{BLACK}Autofill will only update taken branch of conditional orders.
+STR_TIMETABLE_NON_TIMETABLED_BRANCH                             :{BLACK}Not all conditional order branch-taken travel times are timetabled.
 
 
 # Date window (for timetable)
diff --git a/src/timetable_gui.cpp b/src/timetable_gui.cpp
index 65b8b50a49..d7cbf8c70e 100644
--- a/src/timetable_gui.cpp
+++ b/src/timetable_gui.cpp
@@ -569,12 +569,14 @@ struct TimetableWindow : Window {
 					bool have_missing_wait = false;
 					bool have_missing_travel = false;
 					bool have_bad_full_load = false;
+					bool have_non_timetabled_conditional_branch = false;
 
 					const bool assume_timetabled = HasBit(v->vehicle_flags, VF_AUTOFILL_TIMETABLE) || HasBit(v->vehicle_flags, VF_AUTOMATE_TIMETABLE);
 					for (int n = 0; n < v->GetNumOrders(); n++) {
 						const Order *order = v->GetOrder(n);
 						if (order->IsType(OT_CONDITIONAL)) {
 							have_conditional = true;
+							if (!order->IsWaitTimetabled()) have_non_timetabled_conditional_branch = true;
 						} else {
 							if (order->GetWaitTime() == 0 && order->IsType(OT_GOTO_STATION)) {
 								have_missing_wait = true;
@@ -636,6 +638,8 @@ struct TimetableWindow : Window {
 						}
 					}
 					if (have_bad_full_load) draw_info(STR_TIMETABLE_WARNING_FULL_LOAD, true);
+					if (have_conditional && HasBit(v->vehicle_flags, VF_AUTOFILL_TIMETABLE)) draw_info(STR_TIMETABLE_WARNING_AUTOFILL_CONDITIONAL, true);
+					if (total_time && have_non_timetabled_conditional_branch) draw_info(STR_TIMETABLE_NON_TIMETABLED_BRANCH, false);
 
 					if (warning_count != this->summary_warnings) {
 						TimetableWindow *mutable_this = const_cast<TimetableWindow *>(this);