diff --git a/src/ChatPage.h b/src/ChatPage.h
index 5182ab99..46630692 100644
--- a/src/ChatPage.h
+++ b/src/ChatPage.h
@@ -153,6 +153,7 @@ signals:
 
         void updateGroupsInfo(const mtx::responses::JoinedGroups &groups);
         void themeChanged();
+        void decryptSidebarChanged();
 
 private slots:
         void showUnreadMessageNotification(int count);
diff --git a/src/MainWindow.cpp b/src/MainWindow.cpp
index fb64f0fe..c6abdca2 100644
--- a/src/MainWindow.cpp
+++ b/src/MainWindow.cpp
@@ -117,6 +117,10 @@ MainWindow::MainWindow(QWidget *parent)
           userSettingsPage_, SIGNAL(trayOptionChanged(bool)), trayIcon_, SLOT(setVisible(bool)));
         connect(
           userSettingsPage_, &UserSettingsPage::themeChanged, chat_page_, &ChatPage::themeChanged);
+        connect(userSettingsPage_,
+                &UserSettingsPage::decryptSidebarChanged,
+                chat_page_,
+                &ChatPage::decryptSidebarChanged);
         connect(trayIcon_,
                 SIGNAL(activated(QSystemTrayIcon::ActivationReason)),
                 this,
diff --git a/src/Olm.cpp b/src/Olm.cpp
index 78b16be7..c8e4c13c 100644
--- a/src/Olm.cpp
+++ b/src/Olm.cpp
@@ -184,7 +184,7 @@ encrypt_group_message(const std::string &room_id, const std::string &device_id,
         data.relates_to = relation;
 
         auto message_index = olm_outbound_group_session_message_index(res.session);
-        nhlog::crypto()->info("next message_index {}", message_index);
+        nhlog::crypto()->debug("next message_index {}", message_index);
 
         // We need to re-pickle the session after we send a message to save the new message_index.
         cache::updateOutboundMegolmSession(room_id, message_index);
diff --git a/src/UserSettingsPage.cpp b/src/UserSettingsPage.cpp
index 537054c7..4db883f5 100644
--- a/src/UserSettingsPage.cpp
+++ b/src/UserSettingsPage.cpp
@@ -432,6 +432,7 @@ UserSettingsPage::UserSettingsPage(QSharedPointer<UserSettings> settings, QWidge
 
         connect(decryptSidebar_, &Toggle::toggled, this, [this](bool isDisabled) {
                 settings_->setDecryptSidebar(!isDisabled);
+                emit decryptSidebarChanged();
         });
 
         connect(avatarCircles_, &Toggle::toggled, this, [this](bool isDisabled) {
diff --git a/src/UserSettingsPage.h b/src/UserSettingsPage.h
index aff2525a..6b9834ea 100644
--- a/src/UserSettingsPage.h
+++ b/src/UserSettingsPage.h
@@ -183,6 +183,7 @@ signals:
         void moveBack();
         void trayOptionChanged(bool value);
         void themeChanged();
+        void decryptSidebarChanged();
 
 private slots:
         void importSessionKeys();
diff --git a/src/timeline/TimelineModel.cpp b/src/timeline/TimelineModel.cpp
index 439a7786..3e2c32fa 100644
--- a/src/timeline/TimelineModel.cpp
+++ b/src/timeline/TimelineModel.cpp
@@ -502,6 +502,13 @@ isMessage(const mtx::events::Event<T> &)
         return false;
 }
 
+template<typename T>
+auto
+isMessage(const mtx::events::EncryptedEvent<T> &)
+{
+        return true;
+}
+
 void
 TimelineModel::updateLastMessage()
 {
diff --git a/src/timeline/TimelineModel.h b/src/timeline/TimelineModel.h
index 84e9ec26..98b183f6 100644
--- a/src/timeline/TimelineModel.h
+++ b/src/timeline/TimelineModel.h
@@ -189,6 +189,7 @@ public:
         Q_INVOKABLE void cacheMedia(QString eventId);
         Q_INVOKABLE bool saveMedia(QString eventId) const;
 
+        void updateLastMessage();
         void addEvents(const mtx::responses::Timeline &events);
         template<class T>
         void sendMessage(const T &msg);
@@ -257,7 +258,6 @@ private:
                                const std::string &user_id,
                                const mtx::responses::ClaimKeys &res,
                                mtx::http::RequestErr err);
-        void updateLastMessage();
         void readEvent(const std::string &id);
 
         QHash<QString, mtx::events::collections::TimelineEvents> events;
diff --git a/src/timeline/TimelineViewManager.cpp b/src/timeline/TimelineViewManager.cpp
index 0a339825..4562dd67 100644
--- a/src/timeline/TimelineViewManager.cpp
+++ b/src/timeline/TimelineViewManager.cpp
@@ -16,6 +16,19 @@
 
 Q_DECLARE_METATYPE(mtx::events::collections::TimelineEvents)
 
+void
+TimelineViewManager::updateEncryptedDescriptions()
+{
+        QHash<QString, QSharedPointer<TimelineModel>>::iterator i;
+        for (i = models.begin(); i != models.end(); ++i) {
+                auto ptr = i.value();
+
+                if (!ptr.isNull()) {
+                        ptr->updateLastMessage();
+                }
+        }
+}
+
 void
 TimelineViewManager::updateColorPalette()
 {
@@ -83,6 +96,10 @@ TimelineViewManager::TimelineViewManager(QSharedPointer<UserSettings> userSettin
                 &ChatPage::themeChanged,
                 this,
                 &TimelineViewManager::updateColorPalette);
+        connect(dynamic_cast<ChatPage *>(parent),
+                &ChatPage::decryptSidebarChanged,
+                this,
+                &TimelineViewManager::updateEncryptedDescriptions);
 }
 
 void
diff --git a/src/timeline/TimelineViewManager.h b/src/timeline/TimelineViewManager.h
index 122e4aec..45a603af 100644
--- a/src/timeline/TimelineViewManager.h
+++ b/src/timeline/TimelineViewManager.h
@@ -84,6 +84,7 @@ public slots:
                                const QString &url,
                                const QString &mime,
                                uint64_t dsize);
+        void updateEncryptedDescriptions();
 
 private:
 #ifdef USE_QUICK_VIEW