diff --git a/Telegram/SourceFiles/boxes/send_files_box.cpp b/Telegram/SourceFiles/boxes/send_files_box.cpp
index e45b8d21e9..e7d1f80beb 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.cpp
+++ b/Telegram/SourceFiles/boxes/send_files_box.cpp
@@ -533,6 +533,9 @@ void SendFilesBox::pushBlock(int from, int till) {
 		block.takeWidget(),
 		QMargins(0, _inner->count() ? st::sendMediaRowSkip : 0, 0, 0));
 
+	const auto preventDelete =
+		widget->lifetime().make_state<rpl::event_stream<int>>();
+
 	block.itemDeleteRequest(
 	) | rpl::filter([=] {
 		return !_removingIndex;
@@ -543,12 +546,19 @@ void SendFilesBox::pushBlock(int from, int till) {
 			if (index < 0 || index >= _list.files.size()) {
 				return;
 			}
+			// Prevent item delete if it is the only one.
+			if (_list.files.size() == 1) {
+				preventDelete->fire_copy(0);
+				return;
+			}
 			_list.files.erase(_list.files.begin() + index);
 			refreshAllAfterChanges(from);
 		});
 	}, widget->lifetime());
 
-	block.itemReplaceRequest(
+	rpl::merge(
+		block.itemReplaceRequest(),
+		preventDelete->events()
 	) | rpl::start_with_next([=](int index) {
 		const auto replace = [=](Ui::PreparedList list) {
 			if (list.files.empty()) {