diff --git a/CMakeLists.txt b/CMakeLists.txt
index 378aa51..1151cc1 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -38,7 +38,7 @@ option(WITH_OMEMO "Build OMEMO support module" ON)
 # Dependencies
 ## Qt
 if (NOT DEFINED QT_VERSION_MAJOR)
-  find_package(QT NAMES Qt6 Qt5 REQUIRED COMPONENTS Widgets DBus Gui Xml Network Core)
+  find_package(QT NAMES Qt5 REQUIRED COMPONENTS Widgets DBus Gui Xml Network Core)
 else ()
   find_package(Qt${QT_VERSION_MAJOR} REQUIRED COMPONENTS Widgets DBus Gui Xml Network Core)
 endif()
diff --git a/core/handlers/messagehandler.cpp b/core/handlers/messagehandler.cpp
index 2632848..f939b9e 100644
--- a/core/handlers/messagehandler.cpp
+++ b/core/handlers/messagehandler.cpp
@@ -71,26 +71,12 @@ void Core::MessageHandler::onMessageReceived(const QXmppMessage& msg) {
         case QXmppMessage::GroupChat:
             handled = handleGroupMessage(msg);
             break;
-        case QXmppMessage::Error: {
-            std::tuple<bool, QString, QString> ids = getOriginalPendingMessageId(msg.id());
-            if (std::get<0>(ids)) {
-                QString id = std::get<1>(ids);
-                QString jid = std::get<2>(ids);
-                RosterItem* cnt = acc->rh->getRosterItem(jid);
-                QMap<QString, QVariant> cData = {
-                    {"state", static_cast<uint>(Shared::Message::State::error)},
-                    {"errorText", msg.error().text()}
-                };
-                if (cnt != nullptr)
-                    cnt->changeMessage(id, cData);
-
-                emit acc->changeMessage(jid, id, cData);
-                handled = true;
-            } else {
+        case QXmppMessage::Error:
+            handled = handlePendingMessageError(msg.id(), msg.error().text());
+            if (!handled)
                 qDebug() << "received a message with type \"Error\", not sure what to do with it now, skipping";
-            }
-        }
-        break;
+
+            break;
         case QXmppMessage::Headline:
             qDebug() << "received a message with type \"Headline\", not sure what to do with it now, skipping";
             break;
@@ -99,6 +85,27 @@ void Core::MessageHandler::onMessageReceived(const QXmppMessage& msg) {
         logMessage(msg);
 }
 
+bool Core::MessageHandler::handlePendingMessageError(const QString& id, const QString& errorText) {
+    std::tuple<bool, QString, QString> ids = getOriginalPendingMessageId(id);
+    if (std::get<0>(ids)) {
+        QString id = std::get<1>(ids);
+        QString jid = std::get<2>(ids);
+        RosterItem* ri = acc->rh->getRosterItem(jid);
+        QMap<QString, QVariant> cData = {
+            {"state", static_cast<uint>(Shared::Message::State::error)},
+            {"errorText", errorText}
+        };
+        if (ri != nullptr)
+            ri->changeMessage(id, cData);
+
+        emit acc->changeMessage(jid, id, cData);
+        return true;
+    }
+
+    return false;
+}
+
+
 bool Core::MessageHandler::handleChatMessage(const QXmppMessage& msg, bool outgoing, bool forwarded, bool guessing) {
     if (msg.body().size() != 0 || msg.outOfBandUrl().size() > 0) {
         Shared::Message sMsg(Shared::Message::chat);
@@ -182,9 +189,9 @@ void Core::MessageHandler::initializeMessage(Shared::Message& target, const QXmp
     QString id;
 #if (QXMPP_VERSION) >= QT_VERSION_CHECK(1, 3, 0)
     id = source.originId();
-    if (id.size() == 0) {
+    if (id.size() == 0)
         id = source.id();
-    }
+
     target.setStanzaId(source.stanzaId());
     qDebug() << "initializing message with originId:" << source.originId() << ", id:" << source.id() << ", stansaId:" << source.stanzaId();
 #else
@@ -202,24 +209,19 @@ void Core::MessageHandler::initializeMessage(Shared::Message& target, const QXmp
     target.setBody(source.body());
     target.setForwarded(forwarded);
     
-    if (guessing) {
-        if (target.getFromJid() == acc->getBareJid()) {
-            outgoing = true;
-        } else {
-            outgoing = false;
-        }
-    }
+    if (guessing)
+        outgoing = target.getFromJid() == acc->getBareJid();
+
     target.setOutgoing(outgoing);
-    if (time.isValid()) {
+    if (time.isValid())
         target.setTime(time);
-    } else {
+    else
         target.setCurrentTime();
-    }
-    
+
     QString oob = source.outOfBandUrl();
-    if (oob.size() > 0) {
+    if (oob.size() > 0)
         target.setAttachPath(acc->network->addMessageAndCheckForPath(oob, acc->getName(), target.getPenPalJid(), messageId));
-    }
+
     target.setOutOfBandUrl(oob);
 }
 
@@ -249,7 +251,7 @@ void Core::MessageHandler::onCarbonMessageSent(const QXmppMessage& msg) {
 }
 #endif
 
-std::tuple<bool, QString, QString> Core::MessageHandler::getOriginalPendingMessageId(const QString& id) {
+std::tuple<bool, QString, QString> Core::MessageHandler::getOriginalPendingMessageId(const QString& id, bool clear) {
     std::tuple<bool, QString, QString> result({false, "", ""});
     std::map<QString, QString>::const_iterator itr = pendingStateMessages.find(id);
     if (itr != pendingStateMessages.end()) {
@@ -263,12 +265,14 @@ std::tuple<bool, QString, QString> Core::MessageHandler::getOriginalPendingMessa
             else
                 std::get<1>(result) = itr->first;
 
-            pendingCorrectionMessages.erase(itrC);
+            if (clear)
+                pendingCorrectionMessages.erase(itrC);
         } else {
             std::get<1>(result) = itr->first;
         }
 
-        pendingStateMessages.erase(itr);
+        if (clear)
+            pendingStateMessages.erase(itr);
     }
 
     return result;
@@ -281,9 +285,9 @@ void Core::MessageHandler::onReceiptReceived(const QString& jid, const QString&
         QMap<QString, QVariant> cData = {{"state", static_cast<uint>(Shared::Message::State::delivered)}};
         RosterItem* ri = acc->rh->getRosterItem(std::get<2>(ids));
 
-        if (ri != nullptr) {
+        if (ri != nullptr)
             ri->changeMessage(std::get<1>(ids), cData);
-        }
+
         emit acc->changeMessage(std::get<2>(ids), std::get<1>(ids), cData);
     }
 }
@@ -302,45 +306,25 @@ void Core::MessageHandler::performSending(Shared::Message data, const QString& o
     QString id = data.getId();
     qDebug() << "Sending message with id:" << id;
     if (originalId.size() > 0)
-        qDebug() << "To replace one with id:" << originalId;
+        qDebug() << "To replace the one with id:" << originalId;
 
     RosterItem* ri = acc->rh->getRosterItem(jid);
-    bool sent = false;
     if (newMessage && originalId.size() > 0)
         newMessage = false;
 
     QDateTime sendTime = QDateTime::currentDateTimeUtc();
-    if (acc->state == Shared::ConnectionState::connected) {
-        QXmppMessage msg(createPacket(data, sendTime, originalId));
-        
-        sent = acc->client.sendPacket(msg);
-        if (sent) {
-            data.setState(Shared::Message::State::sent);
-        } else {
-            data.setState(Shared::Message::State::error);
-            data.setErrorText("Couldn't send message: internal QXMPP library error, probably need to check out the logs");
-        }
-        
-    } else {
-        data.setState(Shared::Message::State::error);
-        data.setErrorText("You are is offline or reconnecting");
-    }
+    std::pair<Shared::Message::State, QString> result = scheduleSending(data, sendTime, originalId);
+    data.setState(result.first);
+    data.setErrorText(result.second);
     
     QMap<QString, QVariant> changes(getChanges(data, sendTime, newMessage, originalId));
-    
-    QString realId;
-    if (originalId.size() > 0)
-        realId = originalId;
-    else
-        realId = id;
-
     if (ri != nullptr) {
         if (newMessage)
             ri->appendMessageToArchive(data);
          else
-            ri->changeMessage(realId, changes);
+            ri->changeMessage(originalId.isEmpty() ? id : originalId, changes);
 
-        if (sent) {
+        if (data.getState() != Shared::Message::State::error) {
             pendingStateMessages.insert(std::make_pair(id, jid));
             if (originalId.size() > 0)
                 pendingCorrectionMessages.insert(std::make_pair(id, originalId));
@@ -350,9 +334,81 @@ void Core::MessageHandler::performSending(Shared::Message data, const QString& o
         }
     }
     
-    emit acc->changeMessage(jid, realId, changes);
+    emit acc->changeMessage(jid, originalId.isEmpty() ? id : originalId, changes);
 }
 
+std::pair<Shared::Message::State, QString> Core::MessageHandler::scheduleSending(
+    const Shared::Message& message,
+    const QDateTime& sendTime,
+    const QString& originalId
+) {
+    if (acc->state != Shared::ConnectionState::connected)
+        return {Shared::Message::State::error, "You are is offline or reconnecting"};
+
+    QXmppMessage msg = createPacket(message, sendTime, originalId);
+    QString id = msg.id();
+#ifdef WITH_OMEMO
+    if (message.getEncryption() == Shared::EncryptionProtocol::omemo2) {
+        QXmppTask<QXmppE2eeExtension::MessageEncryptResult> task = acc->om->encryptMessage(std::move(msg), std::nullopt);
+        if (task.isFinished()) {
+            const QXmppE2eeExtension::MessageEncryptResult& res = task.result();
+            if (std::holds_alternative<std::unique_ptr<QXmppMessage>>(res)) {
+                const std::unique_ptr<QXmppMessage>& encrypted = std::get<std::unique_ptr<QXmppMessage>>(res);
+                bool success = acc->client.sendPacket(*encrypted.get());
+                if (success)
+                    return {Shared::Message::State::sent, ""};
+                else
+                    return {Shared::Message::State::error, "Error sending successfully encrypted message"};
+            } else if (std::holds_alternative<QXmppError>(res)) {
+                const QXmppError& err = std::get<QXmppError>(res);
+                return {Shared::Message::State::error, err.description};
+            } else {
+                return {Shared::Message::State::error, "Unexpected error ecryptng the message"};
+            }
+        } else {
+            task.then(this, [this, id] (QXmppE2eeExtension::MessageEncryptResult&& result) {
+                if (std::holds_alternative<std::unique_ptr<QXmppMessage>>(result)) {
+                    const std::unique_ptr<QXmppMessage>& encrypted = std::get<std::unique_ptr<QXmppMessage>>(result);
+                    encrypted->setBody("This message is encrypted with OMEMO 2 but could not be decrypted");
+                    bool success = acc->client.sendPacket(*encrypted.get());
+                    if (success) {
+                        std::tuple<bool, QString, QString> ids = getOriginalPendingMessageId(id, false);
+                        if (std::get<0>(ids)) {
+                            QString id = std::get<1>(ids);
+                            QString jid = std::get<2>(ids);
+                            RosterItem* ri = acc->rh->getRosterItem(jid);
+                            QMap<QString, QVariant> cData = {{"state", static_cast<uint>(Shared::Message::State::sent)}};
+                            if (ri != nullptr)
+                                ri->changeMessage(id, cData);
+
+                            emit acc->changeMessage(jid, id, cData);
+                        } else {
+                            qDebug() << "Encrypted message has been successfully sent, but it couldn't be found to update the sate";
+                        }
+                    } else {
+                        handlePendingMessageError(id, "Error sending successfully encrypted message");
+                    }
+                } else if (std::holds_alternative<QXmppError>(result)) {
+                    const QXmppError& err = std::get<QXmppError>(result);
+                    handlePendingMessageError(id, err.description);
+                } else {
+                    handlePendingMessageError(id, "Unexpected error ecryptng the message");
+                }
+            });
+            return {Shared::Message::State::pending, ""};
+        }
+    } else
+#endif
+    {
+        bool success = acc->client.sendPacket(msg);
+        if (success)
+            return {Shared::Message::State::sent, ""};
+        else
+            return {Shared::Message::State::error, "Error sending message, internal QXMPP error"};
+    }
+}
+
+
 QMap<QString, QVariant> Core::MessageHandler::getChanges(Shared::Message& data, const QDateTime& time, bool newMessage, const QString& originalId) const {
     QMap<QString, QVariant> changes;
 
diff --git a/core/handlers/messagehandler.h b/core/handlers/messagehandler.h
index a08fee8..99a77d3 100644
--- a/core/handlers/messagehandler.h
+++ b/core/handlers/messagehandler.h
@@ -23,9 +23,13 @@
 
 #include <deque>
 #include <map>
+#include <functional>
 
 #include <QXmppMessage.h>
 #include <QXmppHttpUploadIq.h>
+#ifdef WITH_OMEMO
+    #include <QXmppE2eeExtension.h>
+#endif
 
 #include <shared/message.h>
 #include <shared/messageinfo.h>
@@ -74,7 +78,9 @@ private:
     void handleUploadError(const QString& jid, const QString& messageId, const QString& errorText);
     QXmppMessage createPacket(const Shared::Message& data, const QDateTime& time, const QString& originalId) const;
     QMap<QString, QVariant> getChanges(Shared::Message& data, const QDateTime& time, bool newMessage, const QString& originalId) const;
-    std::tuple<bool, QString, QString> getOriginalPendingMessageId(const QString& id);
+    std::tuple<bool, QString, QString> getOriginalPendingMessageId(const QString& id, bool clear = true);
+    bool handlePendingMessageError(const QString& id, const QString& errorText);
+    std::pair<Shared::Message::State, QString> scheduleSending(const Shared::Message& message, const QDateTime& sendTime, const QString& originalId);
     
 private:
     Account* acc;
diff --git a/shared/message.cpp b/shared/message.cpp
index dab03a3..5b535c1 100644
--- a/shared/message.cpp
+++ b/shared/message.cpp
@@ -247,6 +247,19 @@ void Shared::Message::setEdited(bool p_edited) {
     edited = p_edited;
 }
 
+Shared::EncryptionProtocol Shared::Message::getEncryption() const {
+    return encryption;
+}
+
+void Shared::Message::setEncryption(EncryptionProtocol encryption) {
+    Shared::Message::encryption = encryption;
+}
+
+void Shared::Message::setError(const QString& text) {
+    state = State::error;
+    errorText = text;
+}
+
 QDataStream& operator<<(QDataStream& out, const Shared::Message& info) {
     out << info.jFrom;
     out << info.rFrom;
@@ -271,6 +284,7 @@ QDataStream& operator<<(QDataStream& out, const Shared::Message& info) {
     }
     out << info.stanzaId;
     out << info.attachPath;
+    out << (quint8)info.encryption;
 
     return out;
 }
@@ -303,6 +317,9 @@ QDataStream & operator>>(QDataStream& in, Shared::Message& info) {
     }
     in >> info.stanzaId;
     in >> info.attachPath;
+    quint8 e;
+    in >> e;
+    info.encryption = static_cast<Shared::EncryptionProtocol>(e);
 
     return in;
 }
diff --git a/shared/message.h b/shared/message.h
index 557b1b3..d7df9f3 100644
--- a/shared/message.h
+++ b/shared/message.h
@@ -25,6 +25,8 @@
 #include <QMap>
 #include <QDataStream>
 
+#include "enums.h"
+
 namespace Shared {
     class Message;
 }
@@ -94,6 +96,9 @@ public:
     bool change(const QMap<QString, QVariant>& data);
     void setStanzaId(const QString& sid);
     void setAttachPath(const QString& path);
+    void setEncryption(EncryptionProtocol encryption);
+
+    void setError(const QString& text);
     
     QString getFrom() const;
     QString getFromJid() const;
@@ -123,6 +128,7 @@ public:
     QString getOriginalBody() const;
     QString getStanzaId() const;
     QString getAttachPath() const;
+    EncryptionProtocol getEncryption() const;
     
 private:
     QString jFrom;
@@ -144,6 +150,7 @@ private:
     QDateTime lastModified;
     QString stanzaId;
     QString attachPath;
+    EncryptionProtocol encryption;
 };
 
 }
diff --git a/ui/widgets/chat.cpp b/ui/widgets/chat.cpp
index 3b9f090..628f30f 100644
--- a/ui/widgets/chat.cpp
+++ b/ui/widgets/chat.cpp
@@ -31,10 +31,12 @@ Chat::Chat(Models::Account* acc, Models::Contact* p_contact, QWidget* parent):
     setAvatar(p_contact->getAvatarPath());
     
     connect(contact, &Models::Contact::childChanged, this, &Chat::onContactChanged);
+#ifdef WITH_OMEMO
     if (p_contact->hasKeys(Shared::EncryptionProtocol::omemo2)) {
         m_ui->encryptionButton->setVisible(true);
-        //if ()
+        updateEncryptionState();
     }
+#endif
 }
 
 Chat::~Chat()
@@ -56,9 +58,14 @@ void Chat::onContactChanged(Models::Item* item, int row, int col) {
             case 7:
                 setAvatar(contact->getAvatarPath());
                 break;
+#ifdef WITH_OMEMO
             case 8:
                 m_ui->encryptionButton->setVisible(contact->hasKeys(Shared::EncryptionProtocol::omemo2));
                 break;
+            case 9:
+                updateEncryptionState();
+                break;
+#endif
         }
     }
 }
@@ -69,12 +76,25 @@ void Chat::updateState() {
     statusIcon->setToolTip(Shared::Global::getName(av));
 }
 
+void Chat::updateEncryptionState() {
+    m_ui->encryptionButton->setEnabled(true);
+    if (contact->getEncryption() == Shared::EncryptionProtocol::omemo2)
+        m_ui->encryptionButton->setIcon(Shared::icon("lock"));
+    else
+        m_ui->encryptionButton->setIcon(Shared::icon("unlock"));
+}
+
+
 Shared::Message Chat::createMessage() const {
     Shared::Message msg = Conversation::createMessage();
     msg.setType(Shared::Message::chat);
     msg.setFrom(account->getFullJid());
     msg.setToJid(palJid);
     msg.setToResource(activePalResource);
+#ifdef WITH_OMEMO
+    if (contact->getEncryption() == Shared::EncryptionProtocol::omemo2)
+        msg.setEncryption(Shared::EncryptionProtocol::omemo2);
+#endif
     return msg;
 }
 
@@ -87,3 +107,11 @@ void Chat::onMessage(const Shared::Message& data){
             setPalResource(res);
     }
 }
+
+void Chat::onEncryptionButtonClicked() {
+    m_ui->encryptionButton->setEnabled(false);
+    if (contact->getEncryption() == Shared::EncryptionProtocol::omemo2)
+        emit setEncryption(Shared::EncryptionProtocol::none);
+    else
+        emit setEncryption(Shared::EncryptionProtocol::omemo2);
+}
diff --git a/ui/widgets/chat.h b/ui/widgets/chat.h
index 78e6bec..cf7ecd3 100644
--- a/ui/widgets/chat.h
+++ b/ui/widgets/chat.h
@@ -37,6 +37,7 @@ public:
 
 protected slots:
     void onContactChanged(Models::Item* item, int row, int col);
+    void onEncryptionButtonClicked() override;
     
 protected:
     Shared::Message createMessage() const override;
@@ -44,6 +45,7 @@ protected:
     
 private:
     void updateState();
+    void updateEncryptionState();
     
 private:
     Models::Contact* contact;
diff --git a/ui/widgets/conversation.cpp b/ui/widgets/conversation.cpp
index e6316c7..8336d5e 100644
--- a/ui/widgets/conversation.cpp
+++ b/ui/widgets/conversation.cpp
@@ -91,6 +91,7 @@ Conversation::Conversation(bool muc, Models::Account* acc, Models::Element* el,
     connect(m_ui->clearButton, &QPushButton::clicked, this, &Conversation::clear);
     connect(m_ui->messageEditor->document()->documentLayout(), &QAbstractTextDocumentLayout::documentSizeChanged, 
             this, &Conversation::onTextEditDocSizeChanged);
+    connect(m_ui->encryptionButton, &QPushButton::clicked, this, &Conversation::onEncryptionButtonClicked);
     
     m_ui->messageEditor->installEventFilter(&ker);
 
@@ -345,6 +346,8 @@ void Conversation::clear() {
     m_ui->messageEditor->clear();
 }
 
+void Conversation::onEncryptionButtonClicked() {}
+
 void Conversation::setAvatar(const QString& path) {
     QPixmap pixmap;
     if (path.size() == 0) {
diff --git a/ui/widgets/conversation.h b/ui/widgets/conversation.h
index 8af1745..4db5029 100644
--- a/ui/widgets/conversation.h
+++ b/ui/widgets/conversation.h
@@ -119,6 +119,7 @@ protected slots:
     void onFeedContext(const QPoint &pos);
     void onMessageEditorContext(const QPoint &pos);
     void onMessageEditRequested(const QString& id);
+    virtual void onEncryptionButtonClicked();
     
 public:
     const bool isMuc;
diff --git a/ui/widgets/messageline/messagefeed.cpp b/ui/widgets/messageline/messagefeed.cpp
index 1eba1fa..29f51d2 100644
--- a/ui/widgets/messageline/messagefeed.cpp
+++ b/ui/widgets/messageline/messagefeed.cpp
@@ -230,6 +230,7 @@ std::set<Models::MessageFeed::MessageRoles> Models::MessageFeed::detectChanges(c
 }
 
 void Models::MessageFeed::removeMessage(const QString& id) {
+    SHARED_UNUSED(id);
     //todo;
 }