diff --git a/include/ChatPage.h b/include/ChatPage.h
index 5cd1c623..c9085848 100644
--- a/include/ChatPage.h
+++ b/include/ChatPage.h
@@ -128,7 +128,7 @@ private:
         template<class Collection>
         void updateUserMetadata(const std::vector<Collection> &collection);
 
-        void retryInitialSync();
+        void retryInitialSync(int status_code = -1);
         //! Update the room with the new notification count.
         void updateRoomNotificationCount(const QString &room_id, uint16_t notification_count);
 
diff --git a/include/MatrixClient.h b/include/MatrixClient.h
index 91e6db28..a433b095 100644
--- a/include/MatrixClient.h
+++ b/include/MatrixClient.h
@@ -147,7 +147,7 @@ signals:
         void getOwnProfileResponse(const QUrl &avatar_url, const QString &display_name);
         void getOwnCommunitiesResponse(const QList<QString> &own_communities);
         void initialSyncCompleted(const mtx::responses::Sync &response);
-        void initialSyncFailed();
+        void initialSyncFailed(int status_code = -1);
         void syncCompleted(const mtx::responses::Sync &response);
         void syncFailed(const QString &msg);
         void joinFailed(const QString &msg);
diff --git a/src/ChatPage.cc b/src/ChatPage.cc
index 93ae562e..571ac67a 100644
--- a/src/ChatPage.cc
+++ b/src/ChatPage.cc
@@ -361,7 +361,7 @@ ChatPage::ChatPage(QSharedPointer<MatrixClient> client,
         });
 
         initialSyncTimer_ = new QTimer(this);
-        connect(initialSyncTimer_, &QTimer::timeout, this, &ChatPage::retryInitialSync);
+        connect(initialSyncTimer_, &QTimer::timeout, this, [this]() { retryInitialSync(); });
 
         syncTimeoutTimer_ = new QTimer(this);
         connect(syncTimeoutTimer_, &QTimer::timeout, this, [this]() {
@@ -965,19 +965,30 @@ ChatPage::setGroupViewState(bool isEnabled)
 }
 
 void
-ChatPage::retryInitialSync()
+ChatPage::retryInitialSync(int status_code)
 {
         initialSyncTimer_->stop();
 
         if (client_->getHomeServer().isEmpty()) {
                 deleteConfigs();
+                resetUI();
+                emit showLoginPage("Sync error. Please try again.");
                 return;
         }
 
-        qWarning() << "Retrying initial sync";
+        // Retry on Bad-Gateway & Gateway-Timeout errors
+        if (status_code == -1 || status_code == 504 || status_code == 502 || status_code == 524) {
+                qWarning() << "retrying initial sync";
 
-        client_->initialSync();
-        initialSyncTimer_->start(INITIAL_SYNC_RETRY_TIMEOUT);
+                client_->initialSync();
+                initialSyncTimer_->start(INITIAL_SYNC_RETRY_TIMEOUT);
+        } else {
+                // Drop into the login screen.
+                deleteConfigs();
+                resetUI();
+
+                emit showLoginPage(QString("Sync error %1. Please try again.").arg(status_code));
+        }
 }
 
 void
diff --git a/src/MatrixClient.cc b/src/MatrixClient.cc
index 544f58cb..5471e410 100644
--- a/src/MatrixClient.cc
+++ b/src/MatrixClient.cc
@@ -401,7 +401,7 @@ MatrixClient::initialSync() noexcept
 
                 if (status == 0 || status >= 400) {
                         qDebug() << "Error code received" << status;
-                        emit initialSyncFailed();
+                        emit initialSyncFailed(status);
                         return;
                 }