diff --git a/Telegram/SourceFiles/apiwrap.cpp b/Telegram/SourceFiles/apiwrap.cpp
index fbc6553cf..932990d62 100644
--- a/Telegram/SourceFiles/apiwrap.cpp
+++ b/Telegram/SourceFiles/apiwrap.cpp
@@ -3607,7 +3607,13 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 
 	auto &histories = history->owner().histories();
 
-	while (TextUtilities::CutPart(sending, left, MaxMessageSize)) {
+	const auto exactWebPage = !message.webPage.url.isEmpty();
+	auto isFirst = true;
+	while (TextUtilities::CutPart(sending, left, MaxMessageSize)
+		|| (isFirst && exactWebPage)) {
+		TextUtilities::Trim(left);
+		const auto isLast = left.empty();
+
 		auto newId = FullMsgId(
 			peer->id,
 			_session->data().nextLocalMessageId());
@@ -3627,17 +3633,23 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 			sendFlags |= MTPmessages_SendMessage::Flag::f_reply_to;
 			mediaFlags |= MTPmessages_SendMedia::Flag::f_reply_to;
 		}
+		const auto ignoreWebPage = message.webPage.removed
+			|| (exactWebPage && !isLast);
+		const auto manualWebPage = exactWebPage
+			&& !ignoreWebPage
+			&& (message.webPage.manual || (isLast && !isFirst));
 		const auto replyHeader = NewMessageReplyHeader(action);
 		MTPMessageMedia media = MTP_messageMediaEmpty();
-		if (message.webPage.removed) {
+		if (ignoreWebPage) {
 			sendFlags |= MTPmessages_SendMessage::Flag::f_no_webpage;
-		} else if (const auto fields = message.webPage; fields.id) {
+		} else if (exactWebPage) {
 			using PageFlag = MTPDmessageMediaWebPage::Flag;
 			using PendingFlag = MTPDwebPagePending::Flag;
+			const auto &fields = message.webPage;
 			const auto page = _session->data().webpage(fields.id);
 			media = MTP_messageMediaWebPage(
 				MTP_flags(PageFlag()
-					| (fields.manual ? PageFlag::f_manual : PageFlag())
+					| (manualWebPage ? PageFlag::f_manual : PageFlag())
 					| (fields.forceLargeMedia
 						? PageFlag::f_force_large_media
 						: PageFlag())
@@ -3645,17 +3657,15 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 						? PageFlag::f_force_small_media
 						: PageFlag())),
 				MTP_webPagePending(
-					MTP_flags(page->url.isEmpty()
-						? PendingFlag()
-						: PendingFlag::f_url),
-					MTP_long(page->id),
-					MTP_string(page->url),
+					MTP_flags(PendingFlag::f_url),
+					MTP_long(fields.id),
+					MTP_string(fields.url),
 					MTP_int(page->pendingTill)));
 		}
 		const auto anonymousPost = peer->amAnonymous();
 		const auto silentPost = ShouldSendSilent(peer, action.options);
 		FillMessagePostFlags(action, peer, flags);
-		if (message.webPage.id && message.webPage.invert) {
+		if (exactWebPage && !ignoreWebPage && message.webPage.invert) {
 			flags |= MessageFlag::InvertMedia;
 			sendFlags |= MTPmessages_SendMessage::Flag::f_invert_media;
 			mediaFlags |= MTPmessages_SendMedia::Flag::f_invert_media;
@@ -3732,9 +3742,9 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 					UnixtimeFromMsgId(response.outerMsgId));
 			}
 		};
-		if (!message.webPage.removed
-			&& (message.webPage.manual || sending.empty())
-			&& !message.webPage.url.isEmpty()) {
+		if (exactWebPage
+			&& !ignoreWebPage
+			&& (manualWebPage || sending.empty())) {
 			histories.sendPreparedMessage(
 				history,
 				action.replyTo,
@@ -3743,7 +3753,7 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 					MTP_flags(mediaFlags),
 					peer->input,
 					Data::Histories::ReplyToPlaceholder(),
-					Data::WebPageForMTP(message.webPage),
+					Data::WebPageForMTP(message.webPage, true),
 					msgText,
 					MTP_long(randomId),
 					MTPReplyMarkup(),
@@ -3768,6 +3778,7 @@ void ApiWrap::sendMessage(MessageToSend &&message) {
 					(sendAs ? sendAs->input : MTP_inputPeerEmpty())
 				), done, fail);
 		}
+		isFirst = false;
 	}
 
 	finishForwarding(action);
diff --git a/Telegram/SourceFiles/chat_helpers/message_field.cpp b/Telegram/SourceFiles/chat_helpers/message_field.cpp
index b988a9b3f..0ef3bceca 100644
--- a/Telegram/SourceFiles/chat_helpers/message_field.cpp
+++ b/Telegram/SourceFiles/chat_helpers/message_field.cpp
@@ -601,6 +601,12 @@ MessageLinksParser::MessageLinksParser(not_null<Ui::InputField*> field)
 	_lifetime = _field->changes(
 	) | rpl::start_with_next([=] {
 		const auto length = _field->getTextWithTags().text.size();
+		if (!length) {
+			_lastLength = 0;
+			_timer.cancel();
+			parse();
+			return;
+		}
 		const auto timeout = (std::abs(length - _lastLength) > 2)
 			? 0
 			: kParseLinksTimeout;
@@ -652,6 +658,7 @@ void MessageLinksParser::parse() {
 	const auto &tags = textWithTags.tags;
 	const auto &markdownTags = _field->getMarkdownTags();
 	if (_disabled || text.isEmpty()) {
+		_ranges = {};
 		_list = QStringList();
 		return;
 	}
@@ -663,7 +670,7 @@ void MessageLinksParser::parse() {
 			|| (tag == Ui::InputField::kTagSpoiler);
 	};
 
-	auto ranges = QVector<LinkRange>();
+	_ranges.clear();
 
 	auto tag = tags.begin();
 	const auto tagsEnd = tags.end();
@@ -672,7 +679,7 @@ void MessageLinksParser::parse() {
 
 		if (Ui::InputField::IsValidMarkdownLink(tag->id)
 			&& !TextUtilities::IsMentionLink(tag->id)) {
-			ranges.push_back({ tag->offset, tag->length, tag->id });
+			_ranges.push_back({ tag->offset, tag->length, tag->id });
 		}
 		++tag;
 	};
@@ -782,20 +789,18 @@ void MessageLinksParser::parse() {
 		processTagsBefore(domainOffset);
 		if (!hasTagsIntersection(range.start + range.length)) {
 			if (markdownTagsAllow(range.start, range.length)) {
-				ranges.push_back(range);
+				_ranges.push_back(range);
 			}
 		}
 		offset = matchOffset = p - start;
 	}
 	processTagsBefore(Ui::kQFixedMax);
 
-	apply(text, ranges);
+	applyRanges(text);
 }
 
-void MessageLinksParser::apply(
-		const QString &text,
-		const QVector<LinkRange> &ranges) {
-	const auto count = int(ranges.size());
+void MessageLinksParser::applyRanges(const QString &text) {
+	const auto count = int(_ranges.size());
 	const auto current = _list.current();
 	const auto computeLink = [&](const LinkRange &range) {
 		return range.custom.isEmpty()
@@ -807,7 +812,7 @@ void MessageLinksParser::apply(
 			return true;
 		}
 		for (auto i = 0; i != count; ++i) {
-			if (computeLink(ranges[i]) != current[i]) {
+			if (computeLink(_ranges[i]) != current[i]) {
 				return true;
 			}
 		}
@@ -818,7 +823,7 @@ void MessageLinksParser::apply(
 	}
 	auto parsed = QStringList();
 	parsed.reserve(count);
-	for (const auto &range : ranges) {
+	for (const auto &range : _ranges) {
 		parsed.push_back(computeLink(range).toString());
 	}
 	_list = std::move(parsed);
diff --git a/Telegram/SourceFiles/chat_helpers/message_field.h b/Telegram/SourceFiles/chat_helpers/message_field.h
index 9c4ba031f..d52d1d670 100644
--- a/Telegram/SourceFiles/chat_helpers/message_field.h
+++ b/Telegram/SourceFiles/chat_helpers/message_field.h
@@ -96,38 +96,38 @@ AutocompleteQuery ParseMentionHashtagBotCommandQuery(
 	not_null<const Ui::InputField*> field,
 	ChatHelpers::ComposeFeatures features);
 
-class MessageLinksParser : private QObject {
+class MessageLinksParser final : private QObject {
 public:
 	MessageLinksParser(not_null<Ui::InputField*> field);
 
 	void parseNow();
 	void setDisabled(bool disabled);
 
-	[[nodiscard]] const rpl::variable<QStringList> &list() const;
+	struct LinkRange {
+		int start = 0;
+		int length = 0;
+		QString custom;
 
-protected:
-	bool eventFilter(QObject *object, QEvent *event) override;
+		friend inline auto operator<=>(
+			const LinkRange&,
+			const LinkRange&) = default;
+		friend inline bool operator==(
+			const LinkRange&,
+			const LinkRange&) = default;
+	};
+
+	[[nodiscard]] const rpl::variable<QStringList> &list() const;
+	[[nodiscard]] const std::vector<LinkRange> &ranges() const;
 
 private:
-	struct LinkRange {
-		int start;
-		int length;
-		QString custom;
-	};
-	friend inline bool operator==(const LinkRange &a, const LinkRange &b) {
-		return (a.start == b.start)
-			&& (a.length == b.length)
-			&& (a.custom == b.custom);
-	}
-	friend inline bool operator!=(const LinkRange &a, const LinkRange &b) {
-		return !(a == b);
-	}
+	bool eventFilter(QObject *object, QEvent *event) override;
 
 	void parse();
-	void apply(const QString &text, const QVector<LinkRange> &ranges);
+	void applyRanges(const QString &text);
 
 	not_null<Ui::InputField*> _field;
 	rpl::variable<QStringList> _list;
+	std::vector<LinkRange> _ranges;
 	int _lastLength = 0;
 	bool _disabled = false;
 	base::Timer _timer;
diff --git a/Telegram/SourceFiles/data/data_histories.cpp b/Telegram/SourceFiles/data/data_histories.cpp
index fb20655a5..b1ba12e13 100644
--- a/Telegram/SourceFiles/data/data_histories.cpp
+++ b/Telegram/SourceFiles/data/data_histories.cpp
@@ -73,10 +73,12 @@ MTPInputReplyTo ReplyToForMTP(
 	return MTPInputReplyTo();
 }
 
-MTPInputMedia WebPageForMTP(const Data::WebPageDraft &draft) {
+MTPInputMedia WebPageForMTP(
+		const Data::WebPageDraft &draft,
+		bool required) {
 	using Flag = MTPDinputMediaWebPage::Flag;
 	return MTP_inputMediaWebPage(
-		MTP_flags(Flag::f_optional
+		MTP_flags((required ? Flag() : Flag::f_optional)
 			| (draft.forceLargeMedia ? Flag::f_force_large_media : Flag())
 			| (draft.forceSmallMedia ? Flag::f_force_small_media : Flag())),
 		MTP_string(draft.url));
diff --git a/Telegram/SourceFiles/data/data_histories.h b/Telegram/SourceFiles/data/data_histories.h
index 3d9472bb0..dd2900a41 100644
--- a/Telegram/SourceFiles/data/data_histories.h
+++ b/Telegram/SourceFiles/data/data_histories.h
@@ -30,7 +30,9 @@ struct WebPageDraft;
 [[nodiscard]] MTPInputReplyTo ReplyToForMTP(
 	not_null<History*> history,
 	FullReplyTo replyTo);
-[[nodiscard]] MTPInputMedia WebPageForMTP(const Data::WebPageDraft &draft);
+[[nodiscard]] MTPInputMedia WebPageForMTP(
+	const Data::WebPageDraft &draft,
+	bool required = false);
 
 class Histories final {
 public:
diff --git a/Telegram/SourceFiles/history/history_widget.cpp b/Telegram/SourceFiles/history/history_widget.cpp
index 9a595520b..6d4985d97 100644
--- a/Telegram/SourceFiles/history/history_widget.cpp
+++ b/Telegram/SourceFiles/history/history_widget.cpp
@@ -3941,6 +3941,9 @@ void HistoryWidget::send(Api::SendOptions options) {
 	session().api().sendMessage(std::move(message));
 
 	clearFieldText();
+	if (_preview) {
+		_preview->apply({ .removed = true });
+	}
 	_saveDraftText = true;
 	_saveDraftStart = crl::now();
 	saveDraft();
diff --git a/Telegram/SourceFiles/history/view/controls/history_view_compose_controls.cpp b/Telegram/SourceFiles/history/view/controls/history_view_compose_controls.cpp
index 9150c5e50..c55046a1f 100644
--- a/Telegram/SourceFiles/history/view/controls/history_view_compose_controls.cpp
+++ b/Telegram/SourceFiles/history/view/controls/history_view_compose_controls.cpp
@@ -530,7 +530,7 @@ void FieldHeader::paintWebPage(Painter &p, not_null<PeerData*> context) {
 	Expects(!!_preview.parsed);
 
 	const auto textTop = st::msgReplyPadding.top();
-	auto previewLeft = st::historyReplySkip + st::msgReplyBarSkip;
+	auto previewLeft = st::historyReplySkip;
 
 	const QRect to(
 		previewLeft,
@@ -1204,6 +1204,9 @@ void ComposeControls::clear() {
 		{},
 		saveTextDraft ? TextUpdateEvent::SaveDraft : TextUpdateEvent());
 	cancelReplyMessage();
+	if (_preview) {
+		_preview->apply({ .removed = true });
+	}
 }
 
 void ComposeControls::setText(const TextWithTags &textWithTags) {
@@ -1755,8 +1758,8 @@ void ComposeControls::fieldChanged() {
 		&& (_textUpdateEvents & TextUpdateEvent::SendTyping));
 	updateSendButtonType();
 	_hasSendText = HasSendText(_field);
-	if (!_hasSendText.current() && _preview) {
-		_preview->apply({});
+	if (!_hasSendText.current() && _preview && !_preview->draft().manual) {
+		_preview->apply({ .removed = true });
 	}
 	if (updateBotCommandShown() || updateLikeShown()) {
 		updateControlsVisibility();
diff --git a/Telegram/SourceFiles/history/view/controls/history_view_webpage_processor.cpp b/Telegram/SourceFiles/history/view/controls/history_view_webpage_processor.cpp
index 909e3508e..a3b402b29 100644
--- a/Telegram/SourceFiles/history/view/controls/history_view_webpage_processor.cpp
+++ b/Telegram/SourceFiles/history/view/controls/history_view_webpage_processor.cpp
@@ -155,6 +155,9 @@ void WebpageProcessor::apply(Data::WebPageDraft draft, bool reparse) {
 	_api.request(base::take(_requestId)).cancel();
 	if (draft.removed) {
 		_draft = draft;
+		if (_parsedLinks.empty()) {
+			_draft.removed = false;
+		}
 		_data = nullptr;
 		_links = QStringList();
 		_link = QString();
@@ -272,6 +275,9 @@ void WebpageProcessor::checkNow(bool force) {
 void WebpageProcessor::checkPreview() {
 	const auto previewRestricted = _history->peer
 		&& _history->peer->amRestricted(ChatRestriction::EmbedLinks);
+	if (_parsedLinks.empty()) {
+		_draft.removed = false;
+	}
 	if (_draft.removed) {
 		return;
 	} else if (previewRestricted) {
diff --git a/Telegram/lib_ui b/Telegram/lib_ui
index b05f7eb91..383b5b8f7 160000
--- a/Telegram/lib_ui
+++ b/Telegram/lib_ui
@@ -1 +1 @@
-Subproject commit b05f7eb915a86f67249904061d70f293066de618
+Subproject commit 383b5b8f7e629475e5f22445167aaa7669c5cdd6