diff --git a/Telegram/SourceFiles/apiwrap.cpp b/Telegram/SourceFiles/apiwrap.cpp
index 9f82ba51c6..bf038ffe00 100644
--- a/Telegram/SourceFiles/apiwrap.cpp
+++ b/Telegram/SourceFiles/apiwrap.cpp
@@ -4212,14 +4212,12 @@ void ApiWrap::sendFiles(
 		std::shared_ptr<SendingAlbum> album,
 		const SendAction &action) {
 	const auto haveCaption = !caption.text.isEmpty();
-	const auto isAlbum = (album != nullptr);
-	if (haveCaption && !list.canAddCaption(isAlbum)) {
+	if (haveCaption && !list.canAddCaption(album != nullptr)) {
 		auto message = MessageToSend(action.history);
-		message.textWithTags = std::move(caption);
+		message.textWithTags = base::take(caption);
 		message.action = action;
 		message.action.clearDraft = false;
 		sendMessage(std::move(message));
-		caption = TextWithTags();
 	}
 
 	const auto to = fileLoadTaskOptions(action);
@@ -4240,7 +4238,7 @@ void ApiWrap::sendFiles(
 			case Ui::PreparedFile::AlbumType::File:
 				type = SendMediaType::File;
 				break;
-			default: Unexpected("AlbumType in uploadFilesAfterConfirmation");
+			default: Unexpected("AlbumType in ApiWrap::sendFiles.");
 			}
 		}
 		tasks.push_back(std::make_unique<FileLoadTask>(
diff --git a/Telegram/SourceFiles/boxes/send_files_box.cpp b/Telegram/SourceFiles/boxes/send_files_box.cpp
index 649d414d3f..b0d0701273 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.cpp
+++ b/Telegram/SourceFiles/boxes/send_files_box.cpp
@@ -94,7 +94,7 @@ void FileDialogCallback(
 rpl::producer<QString> FieldPlaceholder(
 		const Ui::PreparedList &list,
 		SendFilesWay way) {
-	return list.canAddCaption(way.groupMediaInAlbums())
+	return list.canAddCaption(way.groupFiles() && way.sendImagesAsPhotos())
 		? tr::lng_photo_caption()
 		: tr::lng_photos_comment();
 }
@@ -436,7 +436,6 @@ void SendFilesBox::initSendWay() {
 	_sendWay = [&] {
 		auto result = Core::App().settings().sendFilesWay();
 		if (_sendLimit == SendLimit::One) {
-			result.setGroupMediaInAlbums(true);
 			result.setGroupFiles(true);
 			return result;
 		} else if (_list.overrideSendImagesAsPhotos == false) {
@@ -463,15 +462,15 @@ void SendFilesBox::updateCaptionPlaceholder() {
 	if (!_caption) {
 		return;
 	}
-	const auto sendWay = _sendWay.current();
-	if (!_list.canAddCaption(sendWay.groupMediaInAlbums())
+	const auto way = _sendWay.current();
+	if (!_list.canAddCaption(way.groupFiles() && way.sendImagesAsPhotos())
 		&& _sendLimit == SendLimit::One) {
 		_caption->hide();
 		if (_emojiToggle) {
 			_emojiToggle->hide();
 		}
 	} else {
-		_caption->setPlaceholder(FieldPlaceholder(_list, sendWay));
+		_caption->setPlaceholder(FieldPlaceholder(_list, way));
 		_caption->show();
 		if (_emojiToggle) {
 			_emojiToggle->show();
@@ -544,33 +543,27 @@ void SendFilesBox::refreshControls() {
 
 void SendFilesBox::setupSendWayControls() {
 	// #TODO files
-	_groupMediaInAlbums.create(
+	_groupFiles.create(
 		this,
-		"Group media in albums",
-		_sendWay.current().groupMediaInAlbums(),
+		"Group items",
+		_sendWay.current().groupFiles(),
 		st::defaultBoxCheckbox);
 	_sendImagesAsPhotos.create(
 		this,
-		"Send images as photos",
+		"Compress images",
 		_sendWay.current().sendImagesAsPhotos(),
 		st::defaultBoxCheckbox);
-	_groupFiles.create(
-		this,
-		"Group files",
-		_sendWay.current().groupFiles(),
-		st::defaultBoxCheckbox);
 
 	_sendWay.changes(
 	) | rpl::start_with_next([=](SendFilesWay value) {
-		_groupMediaInAlbums->setChecked(value.groupMediaInAlbums());
-		_sendImagesAsPhotos->setChecked(value.sendImagesAsPhotos());
 		_groupFiles->setChecked(value.groupFiles());
+		_sendImagesAsPhotos->setChecked(value.sendImagesAsPhotos());
 	}, lifetime());
 
-	_groupMediaInAlbums->checkedChanges(
+	_groupFiles->checkedChanges(
 	) | rpl::start_with_next([=] {
 		auto sendWay = _sendWay.current();
-		sendWay.setGroupMediaInAlbums(_groupMediaInAlbums->checked());
+		sendWay.setGroupFiles(_groupFiles->checked());
 		_sendWay = sendWay;
 	}, lifetime());
 
@@ -580,13 +573,6 @@ void SendFilesBox::setupSendWayControls() {
 		sendWay.setSendImagesAsPhotos(_sendImagesAsPhotos->checked());
 		_sendWay = sendWay;
 	}, lifetime());
-
-	_groupFiles->checkedChanges(
-	) | rpl::start_with_next([=] {
-		auto sendWay = _sendWay.current();
-		sendWay.setGroupFiles(_groupFiles->checked());
-		_sendWay = sendWay;
-	}, lifetime());
 }
 
 void SendFilesBox::updateSendWayControlsVisibility() {
@@ -594,9 +580,8 @@ void SendFilesBox::updateSendWayControlsVisibility() {
 		return;
 	}
 	const auto onlyOne = (_sendLimit == SendLimit::One);
-	_groupMediaInAlbums->setVisible(!onlyOne);
-	_sendImagesAsPhotos->setVisible(/*_list.hasImagesForCompression()*/true); // #TODO files
 	_groupFiles->setVisible(!onlyOne);
+	_sendImagesAsPhotos->setVisible(/*_list.hasImagesForCompression()*/true); // #TODO files
 }
 
 void SendFilesBox::setupCaption() {
@@ -798,9 +783,8 @@ void SendFilesBox::updateBoxSize() {
 		footerHeight += st::boxPhotoCaptionSkip + _caption->height();
 	}
 	const auto pointers = {
-		_groupMediaInAlbums.data(),
+		_groupFiles.data(),
 		_sendImagesAsPhotos.data(),
-		_groupFiles.data()
 	};
 	for (auto pointer : pointers) {
 		if (pointer && !pointer->isHidden()) {
@@ -864,9 +848,8 @@ void SendFilesBox::updateControlsGeometry() {
 		}
 	}
 	const auto pointers = {
-		_groupMediaInAlbums.data(),
+		_groupFiles.data(),
 		_sendImagesAsPhotos.data(),
-		_groupFiles.data()
 	};
 	for (const auto pointer : ranges::view::reverse(pointers)) {
 		if (pointer && !pointer->isHidden()) {
@@ -905,16 +888,13 @@ void SendFilesBox::send(
 
 	auto way = _sendWay.current();
 	auto oldWay = Core::App().settings().sendFilesWay();
+	if (_groupFiles->isHidden()) {
+		way.setGroupFiles(oldWay.groupFiles());
+	}
 	if (_list.overrideSendImagesAsPhotos == way.sendImagesAsPhotos()
 		|| _sendImagesAsPhotos->isHidden()) {
 		way.setSendImagesAsPhotos(oldWay.sendImagesAsPhotos());
 	}
-	if (_groupMediaInAlbums->isHidden()) {
-		way.setGroupMediaInAlbums(oldWay.groupMediaInAlbums());
-	}
-	if (_groupFiles->isHidden()) {
-		way.setGroupFiles(oldWay.groupFiles());
-	}
 	if (way != oldWay) {
 		Core::App().settings().setSendFilesWay(way);
 		Core::App().saveSettingsDelayed();
diff --git a/Telegram/SourceFiles/boxes/send_files_box.h b/Telegram/SourceFiles/boxes/send_files_box.h
index 25384cdf66..2384852795 100644
--- a/Telegram/SourceFiles/boxes/send_files_box.h
+++ b/Telegram/SourceFiles/boxes/send_files_box.h
@@ -176,9 +176,8 @@ private:
 	base::unique_qptr<ChatHelpers::TabbedPanel> _emojiPanel;
 	base::unique_qptr<QObject> _emojiFilter;
 
-	object_ptr<Ui::Checkbox> _groupMediaInAlbums = { nullptr };
-	object_ptr<Ui::Checkbox> _sendImagesAsPhotos = { nullptr };
 	object_ptr<Ui::Checkbox> _groupFiles = { nullptr };
+	object_ptr<Ui::Checkbox> _sendImagesAsPhotos = { nullptr };
 	rpl::variable<Ui::SendFilesWay> _sendWay = Ui::SendFilesWay();
 
 	rpl::variable<int> _footerHeight = 0;
@@ -190,8 +189,6 @@ private:
 	Fn<void()> _whenReadySend;
 	bool _preparing = false;
 
-	int _lastScrollTop = 0;
-
 	QPointer<Ui::RoundButton> _send;
 	QPointer<Ui::RoundButton> _addFile;
 
diff --git a/Telegram/SourceFiles/history/history_widget.cpp b/Telegram/SourceFiles/history/history_widget.cpp
index c6f3e5d550..c77a230b09 100644
--- a/Telegram/SourceFiles/history/history_widget.cpp
+++ b/Telegram/SourceFiles/history/history_widget.cpp
@@ -4215,60 +4215,34 @@ void HistoryWidget::sendingFilesConfirmed(
 	if (showSendingFilesError(list)) {
 		return;
 	}
-	const auto slowmode = _peer->slowmodeApplied();
-	const auto sendImagesAsPhotos = way.sendImagesAsPhotos();
-	const auto sendType = sendImagesAsPhotos
+	auto groups = DivideByGroups(
+		std::move(list),
+		way,
+		_peer->slowmodeApplied());
+	const auto type = way.sendImagesAsPhotos()
 		? SendMediaType::Photo
 		: SendMediaType::File;
-	const auto groupMedia = way.groupMediaInAlbums() || slowmode;
-	const auto groupFiles = way.groupFiles() || slowmode;
-
-	auto group = Ui::PreparedList();
-
-	// For groupType Type::Video means media album,
-	// Type::File means file album,
-	// Type::None means no grouping.
-	using Type = Ui::PreparedFile::AlbumType;
-	auto groupType = Type::None;
-
-	const auto reply = replyToId();
-	auto sendGroup = [&] {
-		if (group.files.empty()) {
-			return;
-		}
-		const auto album = (groupType == Type::None)
-			? nullptr
-			: std::make_shared<SendingAlbum>();
-		uploadFilesAfterConfirmation(
-			base::take(group),
-			sendType,
-			base::take(caption),
-			reply,
-			options,
-			std::move(album));
-	};
-	for (auto i = 0; i != list.files.size(); ++i) {
-		auto &file = list.files[i];
-		const auto fileGroupType = (file.type == Type::Video)
-			? (groupMedia ? Type::Video : Type::None)
-			: (file.type == Type::Photo)
-			? ((groupMedia && sendImagesAsPhotos)
-				? Type::Video
-				: (groupFiles && !sendImagesAsPhotos)
-				? Type::File
-				: Type::None)
-			: (file.type == Type::File)
-			? (groupFiles ? Type::File : Type::None)
-			: Type::None;
-		if ((!group.files.empty() && groupType != fileGroupType)
-			|| ((groupType != Type::None)
-				&& (group.files.size() == Ui::MaxAlbumItems()))) {
-			sendGroup();
-		}
-		group.files.push_back(std::move(file));
-		groupType = fileGroupType;
+	auto action = Api::SendAction(_history);
+	action.replyTo = replyToId();
+	action.options = options;
+	action.clearDraft = false;
+	if (groups.size() > 1 && !caption.text.isEmpty()) {
+		auto message = Api::MessageToSend(_history);
+		message.textWithTags = base::take(caption);
+		message.action = action;
+		session().api().sendMessage(std::move(message));
 	}
-	sendGroup();
+	for (auto &group : groups) {
+		const auto album = group.grouped
+			? std::make_shared<SendingAlbum>()
+			: nullptr;
+		session().api().sendFiles(
+			std::move(group.list),
+			type,
+			base::take(caption),
+			album,
+			action);
+	};
 }
 
 bool HistoryWidget::confirmSendingFiles(
@@ -4343,38 +4317,6 @@ bool HistoryWidget::confirmSendingFiles(
 	return false;
 }
 
-void HistoryWidget::uploadFilesAfterConfirmation(
-		Ui::PreparedList &&list,
-		SendMediaType type,
-		TextWithTags &&caption,
-		MsgId replyTo,
-		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album) {
-	Assert(canWriteMessage());
-
-	const auto isAlbum = (album != nullptr);
-	if (_peer->slowmodeApplied()
-		&& ((list.files.size() > 1 && !album)
-			|| (!list.files.empty()
-				&& !caption.text.isEmpty()
-				&& !list.canAddCaption(isAlbum)))) {
-		Ui::ShowMultilineToast({
-			.text = { tr::lng_slowmode_no_many(tr::now) },
-		});
-		return;
-	}
-
-	auto action = Api::SendAction(_history);
-	action.replyTo = replyTo;
-	action.options = options;
-	session().api().sendFiles(
-		std::move(list),
-		type,
-		std::move(caption),
-		album,
-		action);
-}
-
 void HistoryWidget::uploadFile(
 		const QByteArray &fileContent,
 		SendMediaType type) {
diff --git a/Telegram/SourceFiles/history/history_widget.h b/Telegram/SourceFiles/history/history_widget.h
index 76b698785d..1a56edba19 100644
--- a/Telegram/SourceFiles/history/history_widget.h
+++ b/Telegram/SourceFiles/history/history_widget.h
@@ -434,15 +434,6 @@ private:
 		bool ctrlShiftEnter);
 
 	void uploadFile(const QByteArray &fileContent, SendMediaType type);
-
-	void uploadFilesAfterConfirmation(
-		Ui::PreparedList &&list,
-		SendMediaType type,
-		TextWithTags &&caption,
-		MsgId replyTo,
-		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album = nullptr);
-
 	void itemRemoved(not_null<const HistoryItem*> item);
 
 	// Updates position of controls around the message field,
diff --git a/Telegram/SourceFiles/history/view/history_view_replies_section.cpp b/Telegram/SourceFiles/history/view/history_view_replies_section.cpp
index 46a0ed4f6b..7c534f7b91 100644
--- a/Telegram/SourceFiles/history/view/history_view_replies_section.cpp
+++ b/Telegram/SourceFiles/history/view/history_view_replies_section.cpp
@@ -621,25 +621,12 @@ bool RepliesWidget::confirmSendingFiles(
 			TextWithTags &&caption,
 			Api::SendOptions options,
 			bool ctrlShiftEnter) {
-		if (showSendingFilesError(list)) {
-			return;
-		}
-		const auto type = way.sendImagesAsPhotos()
-			? SendMediaType::Photo
-			: SendMediaType::File;
-		const auto album = way.groupMediaInAlbums() // #TODO files
-			? std::make_shared<SendingAlbum>()
-			: nullptr;
-		uploadFilesAfterConfirmation(
+		sendingFilesConfirmed(
 			std::move(list),
-			type,
+			way,
 			std::move(caption),
-			replyTo,
 			options,
-			album);
-		if (_composeControls->replyingToMessage().msg == replyTo) {
-			_composeControls->cancelReplyMessage();
-		}
+			ctrlShiftEnter);
 	}));
 	box->setCancelledCallback(crl::guard(this, [=] {
 		_composeControls->setText(text);
@@ -661,6 +648,51 @@ bool RepliesWidget::confirmSendingFiles(
 	return true;
 }
 
+void RepliesWidget::sendingFilesConfirmed(
+		Ui::PreparedList &&list,
+		Ui::SendFilesWay way,
+		TextWithTags &&caption,
+		Api::SendOptions options,
+		bool ctrlShiftEnter) {
+	Expects(list.filesToProcess.empty());
+
+	if (showSendingFilesError(list)) {
+		return;
+	}
+	auto groups = DivideByGroups(
+		std::move(list),
+		way,
+		_history->peer->slowmodeApplied());
+	const auto replyTo = replyToId();
+	const auto type = way.sendImagesAsPhotos()
+		? SendMediaType::Photo
+		: SendMediaType::File;
+	auto action = Api::SendAction(_history);
+	action.replyTo = replyTo ? replyTo : _rootId;
+	action.options = options;
+	action.clearDraft = false;
+	if (groups.size() > 1 && !caption.text.isEmpty()) {
+		auto message = Api::MessageToSend(_history);
+		message.textWithTags = base::take(caption);
+		message.action = action;
+		session().api().sendMessage(std::move(message));
+	}
+	for (auto &group : groups) {
+		const auto album = group.grouped
+			? std::make_shared<SendingAlbum>()
+			: nullptr;
+		session().api().sendFiles(
+			std::move(group.list),
+			type,
+			base::take(caption),
+			album,
+			action);
+	};
+	if (_composeControls->replyingToMessage().msg == replyTo) {
+		_composeControls->cancelReplyMessage();
+	}
+}
+
 bool RepliesWidget::confirmSendingFiles(
 		QImage &&image,
 		QByteArray &&content,
@@ -708,35 +740,6 @@ std::optional<QString> RepliesWidget::writeRestriction() const {
 		ChatRestriction::f_send_messages);
 }
 
-void RepliesWidget::uploadFilesAfterConfirmation(
-		Ui::PreparedList &&list,
-		SendMediaType type,
-		TextWithTags &&caption,
-		MsgId replyTo,
-		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album) {
-	const auto isAlbum = (album != nullptr);
-	if (_history->peer->slowmodeApplied()
-		&& ((list.files.size() > 1 && !album)
-			|| (!list.files.empty()
-				&& !caption.text.isEmpty()
-				&& !list.canAddCaption(isAlbum)))) {
-		Ui::ShowMultilineToast({
-			.text = { tr::lng_slowmode_no_many(tr::now) }
-		});
-		return;
-	}
-	auto action = Api::SendAction(_history);
-	action.replyTo = replyTo ? replyTo : _rootId;
-	action.options = options;
-	session().api().sendFiles(
-		std::move(list),
-		type,
-		std::move(caption),
-		album,
-		action);
-}
-
 void RepliesWidget::pushReplyReturn(not_null<HistoryItem*> item) {
 	if (item->history() == _history && item->replyToTop() == _rootId) {
 		_replyReturns.push_back(item->id);
diff --git a/Telegram/SourceFiles/history/view/history_view_replies_section.h b/Telegram/SourceFiles/history/view/history_view_replies_section.h
index f7a6647408..cde6be8f29 100644
--- a/Telegram/SourceFiles/history/view/history_view_replies_section.h
+++ b/Telegram/SourceFiles/history/view/history_view_replies_section.h
@@ -35,6 +35,7 @@ class FlatButton;
 class HistoryDownButton;
 class PinnedBar;
 struct PreparedList;
+class SendFilesWay;
 } // namespace Ui
 
 namespace Profile {
@@ -207,13 +208,12 @@ private:
 		std::optional<bool> overrideSendImagesAsPhotos = std::nullopt,
 		const QString &insertTextOnCancel = QString());
 	bool showSendingFilesError(const Ui::PreparedList &list) const;
-	void uploadFilesAfterConfirmation(
+	void sendingFilesConfirmed(
 		Ui::PreparedList &&list,
-		SendMediaType type,
+		Ui::SendFilesWay way,
 		TextWithTags &&caption,
-		MsgId replyTo,
 		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album);
+		bool ctrlShiftEnter);
 
 	void sendExistingDocument(not_null<DocumentData*> document);
 	bool sendExistingDocument(
diff --git a/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp b/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
index d16daf465f..8afba643f0 100644
--- a/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
+++ b/Telegram/SourceFiles/history/view/history_view_scheduled_section.cpp
@@ -362,22 +362,12 @@ bool ScheduledWidget::confirmSendingFiles(
 			TextWithTags &&caption,
 			Api::SendOptions options,
 			bool ctrlShiftEnter) {
-		if (showSendingFilesError(list)) {
-			return;
-		}
-		const auto type = way.sendImagesAsPhotos()
-			? SendMediaType::Photo
-			: SendMediaType::File;
-		const auto album = way.groupMediaInAlbums() // #TODO files
-			? std::make_shared<SendingAlbum>()
-			: nullptr;
-		uploadFilesAfterConfirmation(
+		sendingFilesConfirmed(
 			std::move(list),
-			type,
+			way,
 			std::move(caption),
-			MsgId(0),//replyToId(),
 			options,
-			album);
+			ctrlShiftEnter);
 	}));
 	//box->setCancelledCallback(crl::guard(this, [=] {
 	//	_field->setTextWithTags(text);
@@ -399,6 +389,43 @@ bool ScheduledWidget::confirmSendingFiles(
 	return true;
 }
 
+void ScheduledWidget::sendingFilesConfirmed(
+		Ui::PreparedList &&list,
+		Ui::SendFilesWay way,
+		TextWithTags &&caption,
+		Api::SendOptions options,
+		bool ctrlShiftEnter) {
+	Expects(list.filesToProcess.empty());
+
+	if (showSendingFilesError(list)) {
+		return;
+	}
+	auto groups = DivideByGroups(std::move(list), way, false);
+	const auto type = way.sendImagesAsPhotos()
+		? SendMediaType::Photo
+		: SendMediaType::File;
+	auto action = Api::SendAction(_history);
+	action.options = options;
+	action.clearDraft = false;
+	if (groups.size() > 1 && !caption.text.isEmpty()) {
+		auto message = Api::MessageToSend(_history);
+		message.textWithTags = base::take(caption);
+		message.action = action;
+		session().api().sendMessage(std::move(message));
+	}
+	for (auto &group : groups) {
+		const auto album = group.grouped
+			? std::make_shared<SendingAlbum>()
+			: nullptr;
+		session().api().sendFiles(
+			std::move(list),
+			type,
+			base::take(caption),
+			album,
+			action);
+	};
+}
+
 bool ScheduledWidget::confirmSendingFiles(
 		QImage &&image,
 		QByteArray &&content,
@@ -416,35 +443,6 @@ bool ScheduledWidget::confirmSendingFiles(
 	return confirmSendingFiles(std::move(list), insertTextOnCancel);
 }
 
-void ScheduledWidget::uploadFilesAfterConfirmation(
-		Ui::PreparedList &&list,
-		SendMediaType type,
-		TextWithTags &&caption,
-		MsgId replyTo,
-		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album) {
-	const auto isAlbum = (album != nullptr);
-	if (_history->peer->slowmodeApplied()
-		&& ((list.files.size() > 1 && !album)
-			|| (!list.files.empty()
-				&& !caption.text.isEmpty()
-				&& !list.canAddCaption(isAlbum)))) {
-		Ui::ShowMultilineToast({
-			.text = { tr::lng_slowmode_no_many(tr::now) },
-		});
-		return;
-	}
-	auto action = Api::SendAction(_history);
-	action.replyTo = replyTo;
-	action.options = options;
-	session().api().sendFiles(
-		std::move(list),
-		type,
-		std::move(caption),
-		album,
-		action);
-}
-
 void ScheduledWidget::uploadFile(
 		const QByteArray &fileContent,
 		SendMediaType type) {
diff --git a/Telegram/SourceFiles/history/view/history_view_scheduled_section.h b/Telegram/SourceFiles/history/view/history_view_scheduled_section.h
index 56c2377f46..ad7b55a565 100644
--- a/Telegram/SourceFiles/history/view/history_view_scheduled_section.h
+++ b/Telegram/SourceFiles/history/view/history_view_scheduled_section.h
@@ -30,6 +30,7 @@ class PlainShadow;
 class FlatButton;
 class HistoryDownButton;
 struct PreparedList;
+class SendFilesWay;
 } // namespace Ui
 
 namespace Profile {
@@ -173,13 +174,12 @@ private:
 		std::optional<bool> overrideSendImagesAsPhotos = std::nullopt,
 		const QString &insertTextOnCancel = QString());
 	bool showSendingFilesError(const Ui::PreparedList &list) const;
-	void uploadFilesAfterConfirmation(
+	void sendingFilesConfirmed(
 		Ui::PreparedList &&list,
-		SendMediaType type,
+		Ui::SendFilesWay way,
 		TextWithTags &&caption,
-		MsgId replyTo,
 		Api::SendOptions options,
-		std::shared_ptr<SendingAlbum> album);
+		bool ctrlShiftEnter);
 
 	void sendExistingDocument(not_null<DocumentData*> document);
 	bool sendExistingDocument(
diff --git a/Telegram/SourceFiles/storage/details/storage_settings_scheme.cpp b/Telegram/SourceFiles/storage/details/storage_settings_scheme.cpp
index 6550150a88..535deee66a 100644
--- a/Telegram/SourceFiles/storage/details/storage_settings_scheme.cpp
+++ b/Telegram/SourceFiles/storage/details/storage_settings_scheme.cpp
@@ -919,7 +919,7 @@ bool ReadSetting(
 		if (!CheckStreamStatus(stream)) return false;
 
 		auto way = Ui::SendFilesWay();
-		way.setGroupMediaInAlbums(v == 1);
+		way.setGroupFiles(v == 1);
 		way.setSendImagesAsPhotos(v == 1);
 		Core::App().settings().setSendFilesWay(way);
 		context.legacyRead = true;
diff --git a/Telegram/SourceFiles/ui/chat/attach/attach_album_preview.cpp b/Telegram/SourceFiles/ui/chat/attach/attach_album_preview.cpp
index fb67a6d15c..b90cd2609e 100644
--- a/Telegram/SourceFiles/ui/chat/attach/attach_album_preview.cpp
+++ b/Telegram/SourceFiles/ui/chat/attach/attach_album_preview.cpp
@@ -137,7 +137,7 @@ AlbumThumbnail *AlbumPreview::findThumb(QPoint position) const {
 		? st::sendMediaPreviewPhotoSkip
 		: st::sendMediaFileThumbSkip;
 	auto find = [&](const auto &thumb) {
-		if (_sendWay.groupMediaInAlbums()) {
+		if (_sendWay.groupFiles() && _sendWay.sendImagesAsPhotos()) {
 			return thumb->containsPoint(position);
 		} else {
 			const auto bottom = top + (isPhotosWay
@@ -258,13 +258,13 @@ void AlbumPreview::updateSizeAnimated(
 
 void AlbumPreview::updateSize() {
 	const auto newHeight = [&] {
-		if (_sendWay.groupMediaInAlbums()) {
-			return int(std::round(_thumbsHeightAnimation.value(
-				_thumbsHeight)));
-		} else if (_sendWay.sendImagesAsPhotos()) {
+		if (!_sendWay.sendImagesAsPhotos()) {
+			return _filesHeight;
+		} else if (!_sendWay.groupFiles()) {
 			return _photosHeight;
 		} else {
-			return _filesHeight;
+			return int(std::round(_thumbsHeightAnimation.value(
+				_thumbsHeight)));
 		}
 	}();
 	if (height() != newHeight) {
@@ -275,12 +275,12 @@ void AlbumPreview::updateSize() {
 void AlbumPreview::paintEvent(QPaintEvent *e) {
 	Painter p(this);
 
-	if (_sendWay.groupMediaInAlbums()) {
-		paintAlbum(p);
-	} else if (_sendWay.sendImagesAsPhotos()) {
+	if (!_sendWay.sendImagesAsPhotos()) {
+		paintFiles(p, e->rect());
+	} else if (!_sendWay.groupFiles()) {
 		paintPhotos(p, e->rect());
 	} else {
-		paintFiles(p, e->rect());
+		paintAlbum(p);
 	}
 }
 
@@ -409,7 +409,8 @@ void AlbumPreview::mouseMoveEvent(QMouseEvent *e) {
 		applyCursor(style::cur_default);
 		return;
 	}
-	const auto isAlbum = _sendWay.groupMediaInAlbums();
+	const auto isAlbum = _sendWay.sendImagesAsPhotos()
+		&& _sendWay.groupFiles();
 	if (isAlbum && _draggedThumb) {
 		const auto position = e->pos();
 		_draggedThumb->moveInAlbum(position - _draggedStartPosition);
diff --git a/Telegram/SourceFiles/ui/chat/attach/attach_prepare.cpp b/Telegram/SourceFiles/ui/chat/attach/attach_prepare.cpp
index 33edeb0bad..d79be2777a 100644
--- a/Telegram/SourceFiles/ui/chat/attach/attach_prepare.cpp
+++ b/Telegram/SourceFiles/ui/chat/attach/attach_prepare.cpp
@@ -7,6 +7,7 @@ https://github.com/telegramdesktop/tdesktop/blob/master/LEGAL
 */
 #include "ui/chat/attach/attach_prepare.h"
 
+#include "ui/chat/attach/attach_send_files_way.h"
 #include "core/mime_type.h"
 
 namespace Ui {
@@ -21,7 +22,7 @@ PreparedFile::PreparedFile(const QString &path) : path(path) {
 
 PreparedFile::PreparedFile(PreparedFile &&other) = default;
 
-PreparedFile &PreparedFile::operator=(PreparedFile && other) = default;
+PreparedFile &PreparedFile::operator=(PreparedFile &&other) = default;
 
 PreparedFile::~PreparedFile() = default;
 
@@ -90,7 +91,7 @@ bool PreparedList::canBeSentInSlowmodeWith(const PreparedList &other) const {
 	return !hasNonGrouping && (!hasFiles || !hasVideos);
 }
 
-bool PreparedList::canAddCaption(bool groupMediaInAlbums) const {
+bool PreparedList::canAddCaption(bool sendingAlbum) const {
 	if (!filesToProcess.empty()
 		|| files.empty()
 		|| files.size() > kMaxAlbumCount) {
@@ -104,14 +105,18 @@ bool PreparedList::canAddCaption(bool groupMediaInAlbums) const {
 				qstr(".tgs"),
 				Qt::CaseInsensitive);
 		return !isSticker;
-	} else if (!groupMediaInAlbums) {
+	} else if (!sendingAlbum) {
 		return false;
 	}
 	const auto hasFiles = ranges::contains(
 		files,
 		PreparedFile::AlbumType::File,
 		&PreparedFile::type);
-	return !hasFiles;
+	const auto hasNotGrouped = ranges::contains(
+		files,
+		PreparedFile::AlbumType::None,
+		&PreparedFile::type);
+	return !hasFiles && !hasNotGrouped;
 }
 
 int MaxAlbumItems() {
@@ -125,4 +130,53 @@ bool ValidateThumbDimensions(int width, int height) {
 		&& (height < 20 * width);
 }
 
+std::vector<PreparedGroup> DivideByGroups(
+		PreparedList &&list,
+		SendFilesWay way,
+		bool slowmode) {
+	const auto sendImagesAsPhotos = way.sendImagesAsPhotos();
+	const auto groupFiles = way.groupFiles() || slowmode;
+
+	auto group = Ui::PreparedList();
+
+	// For groupType Type::Video means media album,
+	// Type::File means file album,
+	// Type::None means no grouping.
+	using Type = Ui::PreparedFile::AlbumType;
+	auto groupType = Type::None;
+
+	auto result = std::vector<PreparedGroup>();
+	auto pushGroup = [&] {
+		result.push_back(PreparedGroup{
+			.list = base::take(group),
+			.grouped = (groupType != Type::None)
+		});
+	};
+	for (auto i = 0; i != list.files.size(); ++i) {
+		auto &file = list.files[i];
+		const auto fileGroupType = (file.type == Type::Video)
+			? (groupFiles ? Type::Video : Type::None)
+			: (file.type == Type::Photo)
+			? ((groupFiles && sendImagesAsPhotos)
+				? Type::Video
+				: (groupFiles && !sendImagesAsPhotos)
+				? Type::File
+				: Type::None)
+			: (file.type == Type::File)
+			? (groupFiles ? Type::File : Type::None)
+			: Type::None;
+		if ((!group.files.empty() && groupType != fileGroupType)
+			|| ((groupType != Type::None)
+				&& (group.files.size() == Ui::MaxAlbumItems()))) {
+			pushGroup();
+		}
+		group.files.push_back(std::move(file));
+		groupType = fileGroupType;
+	}
+	if (!group.files.empty()) {
+		pushGroup();
+	}
+	return result;
+}
+
 } // namespace Ui
diff --git a/Telegram/SourceFiles/ui/chat/attach/attach_prepare.h b/Telegram/SourceFiles/ui/chat/attach/attach_prepare.h
index 6e6419d9c3..b4f5bc4945 100644
--- a/Telegram/SourceFiles/ui/chat/attach/attach_prepare.h
+++ b/Telegram/SourceFiles/ui/chat/attach/attach_prepare.h
@@ -12,6 +12,8 @@ https://github.com/telegramdesktop/tdesktop/blob/master/LEGAL
 
 namespace Ui {
 
+class SendFilesWay;
+
 struct PreparedFileInformation {
 	struct Image {
 		QImage data;
@@ -37,11 +39,9 @@ struct PreparedFileInformation {
 struct PreparedFile {
 	// File-s can be grouped if 'groupFiles'.
 	// File-s + Photo-s can be grouped if 'groupFiles && !sendImagesAsPhotos'.
-	// Photo-s can be grouped if '(groupFiles && !sendImagesAsPhotos)
-	//   || (groupMediaInAlbums && sendImagesAsPhotos)'.
-	// Photo-s + Video-s can be grouped if 'groupMediaInAlbums
-	//   && sendImagesAsPhotos'.
-	// Video-s can be grouped if 'groupMediaInAlbums'.
+	// Photo-s can be grouped if 'groupFiles'.
+	// Photo-s + Video-s can be grouped if 'groupFiles && sendImagesAsPhotos'.
+	// Video-s can be grouped if 'groupFiles'.
 	enum class AlbumType {
 		File,
 		Photo,
@@ -77,12 +77,15 @@ struct PreparedList {
 	: error(error)
 	, errorData(errorData) {
 	}
+	PreparedList(PreparedList &&other) = default;
+	PreparedList &operator=(PreparedList &&other) = default;
+
 	[[nodiscard]] static PreparedList Reordered(
 		PreparedList &&list,
 		std::vector<int> order);
 	void mergeToEnd(PreparedList &&other, bool cutToAlbumSize = false);
 
-	[[nodiscard]] bool canAddCaption(bool groupMediaInAlbums) const;
+	[[nodiscard]] bool canAddCaption(bool sendingAlbum) const;
 	[[nodiscard]] bool canBeSentInSlowmode() const;
 	[[nodiscard]] bool canBeSentInSlowmodeWith(
 		const PreparedList &other) const;
@@ -94,6 +97,16 @@ struct PreparedList {
 	std::optional<bool> overrideSendImagesAsPhotos;
 };
 
+struct PreparedGroup {
+	PreparedList list;
+	bool grouped = false;
+};
+
+[[nodiscard]] std::vector<PreparedGroup> DivideByGroups(
+	PreparedList &&list,
+	SendFilesWay way,
+	bool slowmode);
+
 [[nodiscard]] int MaxAlbumItems();
 [[nodiscard]] bool ValidateThumbDimensions(int width, int height);
 
diff --git a/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.cpp b/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.cpp
index 00fea6cd3e..159fe396ce 100644
--- a/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.cpp
+++ b/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.cpp
@@ -9,19 +9,11 @@ https://github.com/telegramdesktop/tdesktop/blob/master/LEGAL
 
 namespace Ui {
 
-void SendFilesWay::setGroupMediaInAlbums(bool value) {
-	if (value) {
-		_flags |= (Flag::GroupMediaInAlbums | Flag::SendImagesAsPhotos);
-	} else {
-		_flags &= ~Flag::GroupMediaInAlbums;
-	}
-}
-
 void SendFilesWay::setSendImagesAsPhotos(bool value) {
 	if (value) {
 		_flags |= Flag::SendImagesAsPhotos;
 	} else {
-		_flags &= ~(Flag::SendImagesAsPhotos | Flag::GroupMediaInAlbums);
+		_flags &= ~Flag::SendImagesAsPhotos;
 	}
 }
 
@@ -40,36 +32,23 @@ void SendFilesWay::setGroupFiles(bool value) {
 //};
 
 int32 SendFilesWay::serialize() const {
-	auto result = groupMediaInAlbums()
+	auto result = (sendImagesAsPhotos() && groupFiles())
 		? int32(0)
 		: sendImagesAsPhotos()
 		? int32(1)
+		: groupFiles()
+		? int32(3)
 		: int32(2);
-	if (!groupFiles()) {
-		result |= 0x04;
-	}
 	return result;
 }
 
 std::optional<SendFilesWay> SendFilesWay::FromSerialized(int32 value) {
-	auto result = SendFilesWay();
-	result.setGroupFiles(!(value & 0x04));
-	value &= ~0x04;
-	switch (value) {
-	case 0:
-		result.setGroupMediaInAlbums(true);
-		result.setSendImagesAsPhotos(true);
-		break;
-	case 1:
-		result.setGroupMediaInAlbums(false);
-		result.setSendImagesAsPhotos(true);
-		break;
-	case 2:
-		result.setGroupMediaInAlbums(false);
-		result.setSendImagesAsPhotos(false);
-		break;
-	default: return std::nullopt;
+	if (value < 0 || value > 3) {
+		return std::nullopt;
 	}
+	auto result = SendFilesWay();
+	result.setGroupFiles((value == 0) || (value == 3));
+	result.setSendImagesAsPhotos((value == 0) || (value == 1));
 	return result;
 }
 
diff --git a/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.h b/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.h
index 53cb646c88..d155b14bfb 100644
--- a/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.h
+++ b/Telegram/SourceFiles/ui/chat/attach/attach_send_files_way.h
@@ -19,18 +19,14 @@ enum class AttachButtonType {
 
 class SendFilesWay final {
 public:
-	[[nodiscard]] bool groupMediaInAlbums() const {
-		return (_flags & Flag::GroupMediaInAlbums) != 0;
+	[[nodiscard]] bool groupFiles() const {
+		return (_flags & Flag::GroupFiles) != 0;
 	}
 	[[nodiscard]] bool sendImagesAsPhotos() const {
 		return (_flags & Flag::SendImagesAsPhotos) != 0;
 	}
-	[[nodiscard]] bool groupFiles() const {
-		return (_flags & Flag::GroupFiles);
-	}
-	void setGroupMediaInAlbums(bool value);
-	void setSendImagesAsPhotos(bool value);
 	void setGroupFiles(bool value);
+	void setSendImagesAsPhotos(bool value);
 
 	[[nodiscard]] inline bool operator<(const SendFilesWay &other) const {
 		return _flags < other._flags;
@@ -57,11 +53,10 @@ public:
 
 private:
 	enum class Flag : uchar {
-		GroupMediaInAlbums = (1 << 0),
+		GroupFiles = (1 << 0),
 		SendImagesAsPhotos = (1 << 1),
-		GroupFiles = (1 << 2),
 
-		Default = GroupMediaInAlbums | SendImagesAsPhotos | GroupFiles,
+		Default = GroupFiles | SendImagesAsPhotos,
 	};
 	friend inline constexpr bool is_flag_type(Flag) { return true; };