diff --git a/lib/src/components/message_send_state_icon.dart b/lib/src/components/message_send_state_icon.dart
index 8936ac7..0017d7a 100644
--- a/lib/src/components/message_send_state_icon.dart
+++ b/lib/src/components/message_send_state_icon.dart
@@ -149,7 +149,7 @@ class _MessageSendStateIconState extends State<MessageSendStateIcon> {
       if (message.errorWhileSending) {
         icon =
             FaIcon(FontAwesomeIcons.circleExclamation, size: 12, color: color);
-        text = "Error while sending";
+        text = "Unknown error.";
       }
 
       icons.add(icon);
diff --git a/lib/src/database/daos/messages_dao.dart b/lib/src/database/daos/messages_dao.dart
index 73e5577..f947edc 100644
--- a/lib/src/database/daos/messages_dao.dart
+++ b/lib/src/database/daos/messages_dao.dart
@@ -15,7 +15,10 @@ class MessagesDao extends DatabaseAccessor<TwonlyDatabase>
 
   Stream<List<Message>> watchMessageNotOpened(int contactId) {
     return (select(messages)
-          ..where((t) => t.openedAt.isNull() & t.contactId.equals(contactId))
+          ..where((t) =>
+              t.openedAt.isNull() &
+              t.contactId.equals(contactId) &
+              t.errorWhileSending.equals(false))
           ..orderBy([(t) => OrderingTerm.desc(t.sendAt)]))
         .watch();
   }
@@ -55,8 +58,12 @@ class MessagesDao extends DatabaseAccessor<TwonlyDatabase>
   Future removeOldMessages() {
     return (update(messages)
           ..where((t) =>
-              t.openedAt.isSmallerThanValue(
-                  DateTime.now().subtract(Duration(days: 1))) &
+              (t.openedAt.isSmallerThanValue(
+                    DateTime.now().subtract(Duration(days: 1)),
+                  ) |
+                  (t.sendAt.isSmallerThanValue(
+                          DateTime.now().subtract(Duration(days: 1))) &
+                      t.errorWhileSending.equals(true))) &
               t.kind.equals(MessageKind.textMessage.name)))
         .write(MessagesCompanion(contentJson: Value(null)));
   }
diff --git a/lib/src/views/chats/media_viewer_view.dart b/lib/src/views/chats/media_viewer_view.dart
index 2340c4c..81136fc 100644
--- a/lib/src/views/chats/media_viewer_view.dart
+++ b/lib/src/views/chats/media_viewer_view.dart
@@ -1,7 +1,7 @@
 import 'dart:async';
 import 'dart:convert';
+import 'package:drift/drift.dart' hide Column;
 import 'package:flutter/material.dart';
-import 'package:flutter/services.dart';
 import 'package:font_awesome_flutter/font_awesome_flutter.dart';
 import 'package:lottie/lottie.dart';
 import 'package:no_screenshot/no_screenshot.dart';
@@ -91,7 +91,7 @@ class _MediaViewerViewState extends State<MediaViewerView> {
 
   Future loadCurrentMediaFile({bool showTwonly = false}) async {
     await _noScreenshot.screenshotOff();
-    if (!context.mounted || allMediaFiles.isEmpty) return;
+    if (!context.mounted || allMediaFiles.isEmpty) return nextMediaOrExit();
 
     final current = allMediaFiles.first;
     final MediaMessageContent content =
@@ -137,14 +137,24 @@ class _MediaViewerViewState extends State<MediaViewerView> {
     do {
       if (isDownloading) {
         await Future.delayed(Duration(milliseconds: 10));
+        if (!apiProvider.isConnected) break;
       }
       if (content.downloadToken == null) break;
       imageBytes = await getDownloadedMedia(current, content.downloadToken!);
     } while (isDownloading && imageBytes == null);
 
     isDownloading = false;
-
     if (imageBytes == null) {
+      if (current.downloadState == DownloadState.downloaded) {
+        // When the message should be downloaded but imageBytes are null then a error happened
+        await twonlyDatabase.messagesDao.updateMessageByMessageId(
+          current.messageId,
+          MessagesCompanion(
+            errorWhileSending: Value(true),
+          ),
+        );
+      }
+
       nextMediaOrExit();
       return;
     }