diff --git a/app/sql.js b/app/sql.js
index 034028b5e..0ad34d171 100644
--- a/app/sql.js
+++ b/app/sql.js
@@ -2339,6 +2339,7 @@ async function getUnreadByConversation(conversationId) {
   return map(rows, row => jsonToObject(row.json));
 }
 
+// Note: Sorting here is necessary for getting the last message (with limit 1)
 async function getMessagesByConversation(
   conversationId,
   { limit = 100, receivedAt = Number.MAX_VALUE, type = '%' } = {}
@@ -2349,7 +2350,7 @@ async function getMessagesByConversation(
       conversationId = $conversationId AND
       received_at < $received_at AND
       type LIKE $type
-    ORDER BY received_at DESC
+    ORDER BY sent_at DESC
     LIMIT $limit;
     `,
     {
diff --git a/js/models/messages.js b/js/models/messages.js
index 4bdf62f14..05a7e8e17 100644
--- a/js/models/messages.js
+++ b/js/models/messages.js
@@ -2514,11 +2514,11 @@
   Whisper.MessageCollection = Backbone.Collection.extend({
     model: Whisper.Message,
     comparator(left, right) {
-      if (left.get('received_at') === right.get('received_at')) {
-        return (left.get('sent_at') || 0) - (right.get('sent_at') || 0);
+      if (left.get('sent_at') === right.get('sent_at')) {
+        return (left.get('received_at') || 0) - (right.get('received_at') || 0);
       }
 
-      return (left.get('received_at') || 0) - (right.get('received_at') || 0);
+      return (left.get('sent_at') || 0) - (right.get('sent_at') || 0);
     },
     initialize(models, options) {
       if (options) {
diff --git a/libloki/api.js b/libloki/api.js
index bd252b4b4..54a7a2100 100644
--- a/libloki/api.js
+++ b/libloki/api.js
@@ -226,9 +226,12 @@
     // Send
     const options = { messageType: 'pairing-request' };
     const p = new Promise((resolve, reject) => {
+
+      const timestamp = Date.now();
+
       const outgoingMessage = new textsecure.OutgoingMessage(
         null, // server
-        Date.now(), // timestamp,
+        timestamp,
         [recipientPubKey], // numbers
         content, // message
         true, // silent