diff --git a/Telegram/Resources/langs/lang.strings b/Telegram/Resources/langs/lang.strings
index 3a40020ab..e34a738d3 100644
--- a/Telegram/Resources/langs/lang.strings
+++ b/Telegram/Resources/langs/lang.strings
@@ -1296,6 +1296,7 @@ https://github.com/telegramdesktop/tdesktop/blob/master/LEGAL
 "lng_reminder_messages" = "Reminders";
 "lng_scheduled_date" = "Scheduled for {date}";
 "lng_scheduled_date_until_online" = "Scheduled until online";
+"lng_scheduled_send_until_online" = "Send when online";
 "lng_scheduled_send_now" = "Send message now?";
 "lng_scheduled_send_now_many#one" = "Send {count} message now?";
 "lng_scheduled_send_now_many#other" = "Send {count} messages now?";
diff --git a/Telegram/SourceFiles/api/api_common.h b/Telegram/SourceFiles/api/api_common.h
index 25e737d14..beb73081f 100644
--- a/Telegram/SourceFiles/api/api_common.h
+++ b/Telegram/SourceFiles/api/api_common.h
@@ -21,6 +21,7 @@ struct SendOptions {
 enum class SendType {
 	Normal,
 	Scheduled,
+	ScheduledToUser, // For "Send when online".
 };
 
 struct SendAction {
diff --git a/Telegram/SourceFiles/boxes/send_files_box.cpp b/Telegram/SourceFiles/boxes/send_files_box.cpp
index 3bbd168da..15d82a847 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.cpp
+++ b/Telegram/SourceFiles/boxes/send_files_box.cpp
@@ -1937,7 +1937,9 @@ void SendFilesBox::setInnerFocus() {
 void SendFilesBox::send(
 		Api::SendOptions options,
 		bool ctrlShiftEnter) {
-	if (_sendType == Api::SendType::Scheduled && !options.scheduled) {
+	if ((_sendType == Api::SendType::Scheduled
+		|| _sendType == Api::SendType::ScheduledToUser)
+		&& !options.scheduled) {
 		return sendScheduled();
 	}
 
@@ -1982,9 +1984,12 @@ void SendFilesBox::sendSilent() {
 }
 
 void SendFilesBox::sendScheduled() {
+	const auto type = (_sendType == Api::SendType::ScheduledToUser)
+		? SendMenuType::ScheduledToUser
+		: _sendMenuType;
 	const auto callback = [=](Api::SendOptions options) { send(options); };
 	Ui::show(
-		HistoryView::PrepareScheduleBox(this, _sendMenuType, callback),
+		HistoryView::PrepareScheduleBox(this, type, callback),
 		Ui::LayerOption::KeepOther);
 }
 
diff --git a/Telegram/SourceFiles/boxes/share_box.cpp b/Telegram/SourceFiles/boxes/share_box.cpp
index 49c2b32ee..2ff338970 100644
--- a/Telegram/SourceFiles/boxes/share_box.cpp
+++ b/Telegram/SourceFiles/boxes/share_box.cpp
@@ -413,7 +413,9 @@ void ShareBox::keyPressEvent(QKeyEvent *e) {
 
 SendMenuType ShareBox::sendMenuType() const {
 	const auto selected = _inner->selected();
-	return (selected.size() == 1 && selected.front()->isSelf())
+	return ranges::all_of(selected, HistoryView::CanScheduleUntilOnline)
+		? SendMenuType::ScheduledToUser
+		: (selected.size() == 1 && selected.front()->isSelf())
 		? SendMenuType::Reminder
 		: SendMenuType::Scheduled;
 }
diff --git a/Telegram/SourceFiles/chat_helpers/message_field.cpp b/Telegram/SourceFiles/chat_helpers/message_field.cpp
index c2f3983a5..87012d32f 100644
--- a/Telegram/SourceFiles/chat_helpers/message_field.cpp
+++ b/Telegram/SourceFiles/chat_helpers/message_field.cpp
@@ -688,9 +688,9 @@ void SetupSendMenu(
 		}
 		if (schedule && now != SendMenuType::SilentOnly) {
 			(*menu)->addAction(
-				(now == SendMenuType::Scheduled
-					? tr::lng_schedule_message(tr::now)
-					: tr::lng_reminder_message(tr::now)),
+				(now == SendMenuType::Reminder
+					? tr::lng_reminder_message(tr::now)
+					: tr::lng_schedule_message(tr::now)),
 				schedule);
 		}
 		(*menu)->popup(QCursor::pos());
diff --git a/Telegram/SourceFiles/chat_helpers/message_field.h b/Telegram/SourceFiles/chat_helpers/message_field.h
index 874e15b8e..f6bfd80b9 100644
--- a/Telegram/SourceFiles/chat_helpers/message_field.h
+++ b/Telegram/SourceFiles/chat_helpers/message_field.h
@@ -99,6 +99,7 @@ enum class SendMenuType {
 	Disabled,
 	SilentOnly,
 	Scheduled,
+	ScheduledToUser, // For "Send when online".
 	Reminder,
 };
 
diff --git a/Telegram/SourceFiles/history/history_widget.cpp b/Telegram/SourceFiles/history/history_widget.cpp
index f25f3b113..80b599f93 100644
--- a/Telegram/SourceFiles/history/history_widget.cpp
+++ b/Telegram/SourceFiles/history/history_widget.cpp
@@ -3019,6 +3019,8 @@ SendMenuType HistoryWidget::sendMenuType() const {
 		? SendMenuType::Disabled
 		: _peer->isSelf()
 		? SendMenuType::Reminder
+		: HistoryView::CanScheduleUntilOnline(_peer)
+		? SendMenuType::ScheduledToUser
 		: SendMenuType::Scheduled;
 }
 
diff --git a/Telegram/SourceFiles/history/view/history_view_schedule_box.cpp b/Telegram/SourceFiles/history/view/history_view_schedule_box.cpp
index 64ef33a53..405b9f52f 100644
--- a/Telegram/SourceFiles/history/view/history_view_schedule_box.cpp
+++ b/Telegram/SourceFiles/history/view/history_view_schedule_box.cpp
@@ -8,17 +8,24 @@ https://github.com/telegramdesktop/tdesktop/blob/master/LEGAL
 #include "history/view/history_view_schedule_box.h"
 
 #include "api/api_common.h"
+#include "data/data_peer.h"
+#include "data/data_user.h"
+#include "data/data_scheduled_messages.h" // kScheduledUntilOnlineTimestamp
 #include "lang/lang_keys.h"
 #include "base/unixtime.h"
 #include "boxes/calendar_box.h"
 #include "ui/widgets/input_fields.h"
 #include "ui/widgets/labels.h"
 #include "ui/widgets/buttons.h"
+#include "ui/widgets/popup_menu.h"
 #include "ui/wrap/padding_wrap.h"
 #include "chat_helpers/message_field.h"
+#include "styles/style_info.h"
 #include "styles/style_layers.h"
 #include "styles/style_history.h"
 
+#include <QGuiApplication>
+
 namespace HistoryView {
 namespace {
 
@@ -535,20 +542,38 @@ void TimeInput::startBorderAnimation() {
 	}
 }
 
+void FillSendUntilOnlineMenu(
+		not_null<Ui::IconButton*> button,
+		Fn<void()> callback) {
+	const auto menu = std::make_shared<base::unique_qptr<Ui::PopupMenu>>();
+	button->setClickedCallback([=] {
+		*menu = base::make_unique_q<Ui::PopupMenu>(button);
+		(*menu)->addAction(
+			tr::lng_scheduled_send_until_online(tr::now),
+			std::move(callback));
+		(*menu)->popup(QCursor::pos());
+		return true;
+	});
+}
+
 } // namespace
 
 TimeId DefaultScheduleTime() {
 	return base::unixtime::now() + 600;
 }
 
+bool CanScheduleUntilOnline(not_null<PeerData*> peer) {
+	return !peer->isSelf() && peer->isUser() && !peer->asUser()->isBot();
+}
+
 void ScheduleBox(
 		not_null<Ui::GenericBox*> box,
 		SendMenuType type,
 		FnMut<void(Api::SendOptions)> done,
 		TimeId time) {
-	box->setTitle((type == SendMenuType::Scheduled)
-		? tr::lng_schedule_title()
-		: tr::lng_remind_title());
+	box->setTitle((type == SendMenuType::Reminder)
+		? tr::lng_remind_title()
+		: tr::lng_schedule_title());
 	box->setWidth(st::boxWideWidth);
 
 	const auto date = Ui::CreateChild<rpl::variable<QDate>>(
@@ -637,10 +662,15 @@ void ScheduleBox(
 		}
 		return result;
 	};
-	const auto save = [=](bool silent) {
+	const auto save = [=](bool silent, bool untilOnline = false) {
+		// Pro tip: Hold Ctrl key to send a silent scheduled message!
+		auto ctrl =
+			(QGuiApplication::keyboardModifiers() == Qt::ControlModifier);
 		auto result = Api::SendOptions();
-		result.silent = silent;
-		result.scheduled = collect();
+		result.silent = silent || ctrl;
+		result.scheduled = untilOnline
+			? Data::ScheduledMessages::kScheduledUntilOnlineTimestamp
+			: collect();
 		if (!result.scheduled) {
 			return;
 		}
@@ -664,6 +694,14 @@ void ScheduleBox(
 		[=] { save(true); },
 		nullptr);
 	box->addButton(tr::lng_cancel(), [=] { box->closeBox(); });
+
+	if (type == SendMenuType::ScheduledToUser) {
+		const auto sendUntilOnline = box->addTopButton(st::infoTopBarMenu);
+		FillSendUntilOnlineMenu(
+			sendUntilOnline.data(),
+			[=] { save(false, true); });
+	}
+
 }
 
 } // namespace HistoryView
diff --git a/Telegram/SourceFiles/history/view/history_view_schedule_box.h b/Telegram/SourceFiles/history/view/history_view_schedule_box.h
index 387ee8c3c..6e4e9c3c2 100644
--- a/Telegram/SourceFiles/history/view/history_view_schedule_box.h
+++ b/Telegram/SourceFiles/history/view/history_view_schedule_box.h
@@ -18,6 +18,7 @@ enum class SendMenuType;
 namespace HistoryView {
 
 [[nodiscard]] TimeId DefaultScheduleTime();
+[[nodiscard]] bool CanScheduleUntilOnline(not_null<PeerData*> peer);
 void ScheduleBox(
 	not_null<Ui::GenericBox*> box,
 	SendMenuType type,
diff --git a/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp b/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
index 0730b1869..ce6158100 100644
--- a/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
+++ b/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
@@ -240,7 +240,9 @@ bool ScheduledWidget::confirmSendingFiles(
 		text,
 		boxCompressConfirm,
 		_history->peer->slowmodeApplied() ? SendLimit::One : SendLimit::Many,
-		Api::SendType::Scheduled,
+		CanScheduleUntilOnline(_history->peer)
+			? Api::SendType::ScheduledToUser
+			: Api::SendType::Scheduled,
 		SendMenuType::Disabled);
 	//_field->setTextWithTags({});
 
@@ -545,6 +547,8 @@ void ScheduledWidget::sendInlineResult(
 SendMenuType ScheduledWidget::sendMenuType() const {
 	return _history->peer->isSelf()
 		? SendMenuType::Reminder
+		: HistoryView::CanScheduleUntilOnline(_history->peer)
+		? SendMenuType::ScheduledToUser
 		: SendMenuType::Scheduled;
 }