diff --git a/qml/component/ImageBubble.qml b/qml/component/ImageBubble.qml
index 2c96cf6..23cf527 100644
--- a/qml/component/ImageBubble.qml
+++ b/qml/component/ImageBubble.qml
@@ -20,7 +20,7 @@ AvatarContainer {
 
             Image {
                 id: messageImage
-                source: "image://mxc/" + content.url
+                source: "image://mxc/" + (content.thumbnail_url ? content.thumbnail_url : content.url)
 
                 MouseArea {
                     anchors.fill: parent
diff --git a/qml/form/RoomForm.qml b/qml/form/RoomForm.qml
index e93c79b..121aada 100644
--- a/qml/form/RoomForm.qml
+++ b/qml/form/RoomForm.qml
@@ -150,12 +150,12 @@ Item {
                             folder: shortcuts.home
                             selectMultiple: false
                             onAccepted: {
-                                currentRoom.uploadFile(fileDialog.fileUrl, fileDialog.fileUrl)
+                                currentRoom.uploadFile(fileUrl, fileUrl, matriqueController.getMIME(fileUrl))
                                 var fileTransferProgressCallback = function(id, sent, total) {
-                                    if (id == fileDialog.fileUrl) { inputField.progress = sent / total }
+                                    if (id == fileUrl) { inputField.progress = sent / total }
                                 }
                                 var completedCallback = function(id, localFile, mxcUrl) {
-                                    if (id == fileDialog.fileUrl) {
+                                    if (id == fileUrl) {
                                         matriqueController.postFile(currentRoom, localFile, mxcUrl)
                                         inputField.progress = 0
                                         currentRoom.fileTransferCompleted.disconnect(fileTransferProgressCallback)
diff --git a/src/controller.cpp b/src/controller.cpp
index ce11df4..04e7c8a 100644
--- a/src/controller.cpp
+++ b/src/controller.cpp
@@ -4,6 +4,10 @@
 #include "events/eventcontent.h"
 #include "events/roommessageevent.h"
 
+#include <QFile>
+#include <QImage>
+#include <QMimeDatabase>
+
 Controller::Controller(QObject* parent) : QObject(parent) {
   connect(m_connection, &QMatrixClient::Connection::connected, this,
           &Controller::connected);
@@ -22,7 +26,11 @@ Controller::Controller(QObject* parent) : QObject(parent) {
           [=] { setBusy(false); });
 }
 
-Controller::~Controller() { m_connection->stopSync(); }
+Controller::~Controller() {
+  m_connection->saveState();
+  m_connection->stopSync();
+  m_connection->deleteLater();
+}
 
 void Controller::login() {
   if (!isLogin) {
@@ -81,10 +89,22 @@ void Controller::reconnect() {
 
 void Controller::postFile(QMatrixClient::Room* room, const QUrl& localFile,
                           const QUrl& mxcUrl) {
-  QJsonObject json{{"body", localFile.fileName()},
-                   {"filename", localFile.fileName()},
-                   {"url", mxcUrl.url()}};
-  room->postMessage(QMatrixClient::RoomMessageEvent{
-      localFile.fileName(), "m.file",
-      new QMatrixClient::EventContent::FileContent(json)});
+  const QString mime = getMIME(localFile);
+  const QString fileName = localFile.toLocalFile();
+  QString msgType = "m.file";
+  if (mime.startsWith("image")) msgType = "m.image";
+  if (mime.startsWith("video")) msgType = "m.video";
+  if (mime.startsWith("audio")) msgType = "m.audio";
+  QJsonObject json{{"content", QJsonObject{{"msgtype", msgType},
+                                           {"body", fileName},
+                                           {"filename", fileName},
+                                           {"url", mxcUrl.url()}}}};
+  room->postMessage(QMatrixClient::RoomMessageEvent(json));
+}
+
+QString Controller::getMIME(const QUrl& fileUrl) const {
+  QMimeDatabase* db = new QMimeDatabase();
+  const QString mime = db->mimeTypeForFile(fileUrl.toLocalFile()).name();
+  free(db);
+  return mime;
 }
diff --git a/src/controller.h b/src/controller.h
index ef388a2..2562a0f 100644
--- a/src/controller.h
+++ b/src/controller.h
@@ -99,6 +99,7 @@ class Controller : public QObject {
  public slots:
   void postFile(QMatrixClient::Room* room, const QUrl& localFile,
                 const QUrl& mxcUrl);
+  QString getMIME(const QUrl& fileUrl) const;
 };
 
 #endif  // CONTROLLER_H