diff --git a/Telegram/SourceFiles/apiwrap.cpp b/Telegram/SourceFiles/apiwrap.cpp
index 589b842a13..eff5a0107e 100644
--- a/Telegram/SourceFiles/apiwrap.cpp
+++ b/Telegram/SourceFiles/apiwrap.cpp
@@ -3838,7 +3838,8 @@ void ApiWrap::sendFiles(
 		TextWithTags &&caption,
 		std::shared_ptr<SendingAlbum> album,
 		const SendAction &action) {
-	const auto haveCaption = !caption.text.isEmpty();
+	auto sharedCaption = std::move(caption);
+	const auto haveCaption = !sharedCaption.text.isEmpty();
 	const auto captionAttached = !haveCaption
 		? false
 		: (list.files.size() == 1)
@@ -3856,10 +3857,12 @@ void ApiWrap::sendFiles(
 			false);
 	if (haveCaption && !captionAttached) {
 		auto message = MessageToSend(action);
-		message.textWithTags = base::take(caption);
+		message.textWithTags = base::take(sharedCaption);
 		message.action.clearDraft = false;
 		sendMessage(std::move(message));
 	}
+	auto attachSharedCaption = haveCaption && captionAttached;
+	auto sharedCaptionConsumed = false;
 
 	const auto to = FileLoadTaskOptions(action);
 	if (album) {
@@ -3868,6 +3871,13 @@ void ApiWrap::sendFiles(
 	auto tasks = std::vector<std::unique_ptr<Task>>();
 	tasks.reserve(list.files.size());
 	for (auto &file : list.files) {
+		auto fileCaption = std::move(file.caption);
+		if (attachSharedCaption && !sharedCaptionConsumed) {
+			sharedCaptionConsumed = true;
+			if (fileCaption.text.isEmpty()) {
+				fileCaption = base::take(sharedCaption);
+			}
+		}
 		const auto uploadWithType = !album
 			? type
 			: (file.type == Ui::PreparedFile::Type::Photo
@@ -3899,14 +3909,13 @@ void ApiWrap::sendFiles(
 				: nullptr),
 			.type = uploadWithType,
 			.to = to,
-			.caption = caption,
+			.caption = std::move(fileCaption),
 			.spoiler = file.spoiler,
 			.album = album,
 			.forceFile = forceFile,
 			.idOverride = 0,
 			.displayName = file.displayName,
 		}));
-		caption = TextWithTags();
 	}
 	if (album) {
 		_sendingAlbums.emplace(album->groupId, album);
diff --git a/Telegram/SourceFiles/boxes/send_files_box.cpp b/Telegram/SourceFiles/boxes/send_files_box.cpp
index b658e8fd89..ccd4d0536c 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.cpp
+++ b/Telegram/SourceFiles/boxes/send_files_box.cpp
@@ -781,6 +781,65 @@ bool SendFilesBox::setDisplayNameInSingleFilePreview(
 	return false;
 }
 
+bool SendFilesBox::setCaptionInSingleFilePreview(
+		int fileIndex,
+		const TextWithTags &caption) {
+	for (auto &block : _blocks) {
+		if (fileIndex < block.fromIndex() || fileIndex >= block.tillIndex()) {
+			continue;
+		}
+		return block.setSingleFileCaption(fileIndex, caption);
+	}
+	return false;
+}
+
+bool SendFilesBox::mainCaptionWillBeAttached() const {
+	const auto way = _sendWay.current();
+	const auto slowmode = (_limits & SendFilesAllow::OnlyOne)
+		&& (_list.files.size() > 1);
+	return Ui::CaptionWillBeAttached(_list, way, slowmode);
+}
+
+void SendFilesBox::applyMainCaptionToFirstFile() {
+	if (!_caption
+		|| _caption->isHidden()
+		|| (_list.files.size() <= 1)
+		|| _list.files.empty()) {
+		if (_mainCaptionAttachedToFirstFile && !_list.files.empty()) {
+			_list.files.front().caption = _firstFileCaptionBackup.value_or(
+				TextWithTags());
+			if (!setCaptionInSingleFilePreview(
+				0,
+				_list.files.front().caption)) {
+			}
+		}
+		_mainCaptionAttachedToFirstFile = false;
+		_firstFileCaptionBackup = std::nullopt;
+		return;
+	}
+	if (mainCaptionWillBeAttached()) {
+		if (!_mainCaptionAttachedToFirstFile) {
+			_firstFileCaptionBackup = _list.files.front().caption;
+		}
+		auto text = _caption->getTextWithAppliedMarkdown();
+		_list.files.front().caption = text;
+		_mainCaptionAttachedToFirstFile = true;
+		if (!setCaptionInSingleFilePreview(
+			0,
+			text)) {
+		}
+	} else if (_mainCaptionAttachedToFirstFile) {
+		_list.files.front().caption = _firstFileCaptionBackup.value_or(
+			TextWithTags());
+		_mainCaptionAttachedToFirstFile = false;
+		_firstFileCaptionBackup = std::nullopt;
+		if (!setCaptionInSingleFilePreview(
+			0,
+			_list.files.front().caption)) {
+		}
+	}
+}
+
 void SendFilesBox::openDialogToAddFileToAlbum() {
 	const auto show = uiShow();
 	const auto checkResult = [=](const Ui::PreparedList &list) {
@@ -810,10 +869,7 @@ void SendFilesBox::openDialogToAddFileToAlbum() {
 }
 
 void SendFilesBox::refreshMessagesCount() {
-	const auto way = _sendWay.current();
-	const auto slowmode = (_limits & SendFilesAllow::OnlyOne)
-		&& (_list.files.size() > 1);
-	const auto withCaption = Ui::CaptionWillBeAttached(_list, way, slowmode);
+	const auto withCaption = mainCaptionWillBeAttached();
 	const auto withComment = !withCaption
 		&& _caption
 		&& !_caption->isHidden()
@@ -1423,6 +1479,7 @@ void SendFilesBox::refreshControls(bool initial) {
 	refreshTitleText();
 	updateSendWayControls();
 	updateCaptionPlaceholder();
+	applyMainCaptionToFirstFile();
 }
 
 void SendFilesBox::setupSendWayControls() {
@@ -1613,6 +1670,7 @@ void SendFilesBox::setupCaption() {
 		_caption->changes()
 	) | rpl::on_next([=] {
 		checkCharsLimitation();
+		applyMainCaptionToFirstFile();
 		refreshMessagesCount();
 	}, _caption->lifetime());
 }
@@ -2028,14 +2086,20 @@ void SendFilesBox::saveSendWaySettings() {
 }
 
 bool SendFilesBox::validateLength(const QString &text) const {
+	const auto way = _sendWay.current();
+	if (!_list.canAddCaption(
+			way.groupFiles() && way.sendImagesAsPhotos(),
+			way.sendImagesAsPhotos())) {
+		return true;
+	}
+	return validateSingleCaptionLength(text);
+}
+
+bool SendFilesBox::validateSingleCaptionLength(const QString &text) const {
 	const auto session = &_show->session();
 	const auto limit = Data::PremiumLimits(session).captionLengthCurrent();
 	const auto remove = int(text.size()) - limit;
-	const auto way = _sendWay.current();
-	if (remove <= 0
-		|| !_list.canAddCaption(
-			way.groupFiles() && way.sendImagesAsPhotos(),
-			way.sendImagesAsPhotos())) {
+	if (remove <= 0) {
 		return true;
 	}
 	_show->showBox(
@@ -2074,6 +2138,7 @@ void SendFilesBox::send(
 	applyBlockChanges();
 
 	Storage::ApplyModifications(_list);
+	applyMainCaptionToFirstFile();
 
 	_confirmed = true;
 	if (_confirmedCallback) {
@@ -2083,6 +2148,11 @@ void SendFilesBox::send(
 		if (!validateLength(caption.text)) {
 			return;
 		}
+		for (const auto &file : _list.files) {
+			if (!validateSingleCaptionLength(file.caption.text)) {
+				return;
+			}
+		}
 		options.invertCaption = _invertCaption;
 		options.price = hasPrice() ? _price.current() : 0;
 		if (options.price > 0) {
diff --git a/Telegram/SourceFiles/boxes/send_files_box.h b/Telegram/SourceFiles/boxes/send_files_box.h
index 18d1fec84f..cf0c9490f0 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.h
+++ b/Telegram/SourceFiles/boxes/send_files_box.h
@@ -256,6 +256,9 @@ private:
 	[[nodiscard]] bool setDisplayNameInSingleFilePreview(
 		int fileIndex,
 		const QString &displayName);
+	[[nodiscard]] bool setCaptionInSingleFilePreview(
+		int fileIndex,
+		const TextWithTags &caption);
 
 	void enqueueNextPrepare();
 	void addPreparedAsyncFile(Ui::PreparedFile &&file);
@@ -264,6 +267,9 @@ private:
 	void refreshMessagesCount();
 
 	void requestToTakeTextWithTags() const;
+	bool validateSingleCaptionLength(const QString &text) const;
+	bool mainCaptionWillBeAttached() const;
+	void applyMainCaptionToFirstFile();
 
 	[[nodiscard]] Fn<MenuDetails()> prepareSendMenuDetails(
 		const SendFilesBoxDescriptor &descriptor);
@@ -294,6 +300,8 @@ private:
 	QImage _priceTagBg;
 	bool _confirmed = false;
 	bool _invertCaption = false;
+	bool _mainCaptionAttachedToFirstFile = false;
+	std::optional<TextWithTags> _firstFileCaptionBackup;
 
 	object_ptr<Ui::InputField> _caption = { nullptr };
 	std::unique_ptr<ChatHelpers::FieldAutocomplete> _autocomplete;