diff --git a/ui/widgets/conversation.cpp b/ui/widgets/conversation.cpp
index ab5f0c5..4e5e007 100644
--- a/ui/widgets/conversation.cpp
+++ b/ui/widgets/conversation.cpp
@@ -513,8 +513,9 @@ void Conversation::onFeedContext(const QPoint& pos)
             });
         }
 
+        bool hasAttach = item->getAttachPath() > 0 || item->getOutOfBandUrl() > 0;
         //the only mandatory condition - is for the message to be outgoing, the rest is just a good intention on the server
-        if (item->getOutgoing() && index.row() < 100 && item->getTime().daysTo(QDateTime::currentDateTimeUtc()) < 20) {
+        if (item->getOutgoing() && !hasAttach  && index.row() < 100 && item->getTime().daysTo(QDateTime::currentDateTimeUtc()) < 20) {
             showMenu = true;
             QAction* edit = contextMenu->addAction(Shared::icon("edit-rename"), tr("Edit"));
             connect(edit, &QAction::triggered, this, std::bind(&Conversation::onMessageEditRequested, this, id));
@@ -549,6 +550,10 @@ void Conversation::onMessageEditRequested(const QString& id)
         m_ui->currentActionBadge->setText(tr("Editing message..."));
         currentAction = CurrentAction::edit;
         m_ui->messageEditor->setText(msg.getBody());
+        QString path = msg.getAttachPath();
+        if (path.size() > 0) {
+            addAttachedFile(path);
+        }
 
     } catch (const Models::MessageFeed::NotFound& e) {
         qDebug() << "The message requested to be edited was not found" << e.getMessage().c_str();