diff --git a/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java b/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
index ee51cf743b58e430cb165b04e9f9575ce22bd4c8..600136144dbca544fa4527d3c7b9078191f12f68 100644
--- a/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
+++ b/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
@@ -102,18 +102,25 @@ public class MessageGenerator extends AbstractGenerator {
 
     public MessagePacket generateChat(Message message) {
         MessagePacket packet = preparePacket(message);
-        String content;
         if (message.hasFileOnRemoteHost()) {
             final Message.FileParams fileParams = message.getFileParams();
-            content = fileParams.url;
-            packet.addChild("x", Namespace.OOB).addChild("url").setContent(content);
-            packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", Namespace.OOB)
-                  .addChild("body", "urn:xmpp:fallback:0");
-            message.setBody(content);
-        } else {
-            content = message.getBody();
+
+            if (message.getBody().equals("")) {
+                message.setBody(fileParams.url);
+                packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", Namespace.OOB)
+                      .addChild("body", "urn:xmpp:fallback:0");
+            } else {
+                long start = message.getQuoteableBody().length();
+                message.appendBody(fileParams.url);
+                packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", Namespace.OOB)
+                      .addChild("body", "urn:xmpp:fallback:0")
+                          .setAttribute("start", String.valueOf(start))
+                          .setAttribute("end", String.valueOf(start + fileParams.url.length()));
+            }
+
+            packet.addChild("x", Namespace.OOB).addChild("url").setContent(fileParams.url);
         }
-        packet.setBody(content);
+        packet.setBody(message.getQuoteableBody());
         return packet;
     }
 
diff --git a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
index 652a35233790bfc7e8ef69e176a8ba1d3493c4db..fcbbc2451aa09c2ec9a93b08397ce4a5ced9b18e 100644
--- a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
+++ b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
@@ -616,10 +616,14 @@ public class XmppConnectionService extends Service {
 
     public void attachFileToConversation(final Conversation conversation, final Uri uri, final String type, final UiCallback<Message> callback) {
         final Message message;
-        if (conversation.getNextEncryption() == Message.ENCRYPTION_PGP) {
-            message = new Message(conversation, "", Message.ENCRYPTION_DECRYPTED);
-        } else {
+        if (conversation.getReplyTo() == null) {
             message = new Message(conversation, "", conversation.getNextEncryption());
+        } else {
+            message = conversation.getReplyTo().reply();
+            message.setEncryption(conversation.getNextEncryption());
+        }
+        if (conversation.getNextEncryption() == Message.ENCRYPTION_PGP) {
+            message.setEncryption(Message.ENCRYPTION_DECRYPTED);
         }
         message.setThread(conversation.getThread());
         if (!Message.configurePrivateFileMessage(message)) {
@@ -649,10 +653,15 @@ public class XmppConnectionService extends Service {
             return;
         }
         final Message message;
-        if (conversation.getNextEncryption() == Message.ENCRYPTION_PGP) {
-            message = new Message(conversation, "", Message.ENCRYPTION_DECRYPTED);
-        } else {
+
+        if (conversation.getReplyTo() == null) {
             message = new Message(conversation, "", conversation.getNextEncryption());
+        } else {
+            message = conversation.getReplyTo().reply();
+            message.setEncryption(conversation.getNextEncryption());
+        }
+        if (conversation.getNextEncryption() == Message.ENCRYPTION_PGP) {
+            message.setEncryption(Message.ENCRYPTION_DECRYPTED);
         }
         message.setThread(conversation.getThread());
         if (!Message.configurePrivateFileMessage(message)) {
diff --git a/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java b/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
index a855dcadaea336eef80b2fa5557fd60a5a8eb1b0..2585957e85ba73f7f9e0c5b4c68901fe8a3e42d7 100644
--- a/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
+++ b/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
@@ -807,7 +807,10 @@ public class ConversationFragment extends XmppFragment
 
                     @Override
                     public void success(Message message) {
-                        runOnUiThread(() -> activity.hideToast());
+                        runOnUiThread(() -> {
+                            activity.hideToast();
+                            setupReply(null);
+                        });
                         hidePrepareFileToast(prepareFileToast);
                     }
 
@@ -852,6 +855,7 @@ public class ConversationFragment extends XmppFragment
                     @Override
                     public void success(Message message) {
                         hidePrepareFileToast(prepareFileToast);
+                        runOnUiThread(() -> setupReply(null));
                     }
 
                     @Override
@@ -1125,7 +1129,6 @@ public class ConversationFragment extends XmppFragment
         } else {
             activity.selectPresence(conversation, callback);
         }
-        setupReply(null);
     }
 
     private static boolean anyNeedsExternalStoragePermission(