diff --git a/lib/handlers/connect.js b/lib/handlers/connect.js
index 0f1a9723..14865f36 100644
--- a/lib/handlers/connect.js
+++ b/lib/handlers/connect.js
@@ -232,7 +232,11 @@ function emptyQueue (arg, done) {
     outgoing,
     through(function clearQueue (data, enc, next) {
       const packet = new QoSPacket(data, client)
-      packet.writeCallback = next
+      // Here we are deliberatly passing only the error
+      // This is because there is no destination stream so the "client"
+      // Object filled the buffer up to the highWaterMark preventing stored messages
+      // being sent
+      packet.writeCallback = (error, _client) => next(error)
       persistence.outgoingUpdate(client, packet, emptyQueueFilter)
     }),
     done
diff --git a/test/qos1.js b/test/qos1.js
index 8963701a..baac1dce 100644
--- a/test/qos1.js
+++ b/test/qos1.js
@@ -509,6 +509,71 @@ test('resend publish on non-clean reconnect QoS 1', function (t) {
   })
 })
 
+test('resend many publish on non-clean reconnect QoS 1', function (t) {
+  t.plan(38)
+
+  const broker = aedes()
+  t.tearDown(broker.close.bind(broker))
+
+  const opts = { clean: false, clientId: 'abcde' }
+  let subscriber = connect(setup(broker), opts)
+
+  subscribe(t, subscriber, 'hello', 1, function () {
+    subscriber.inStream.end()
+
+    const publisher = connect(setup(broker))
+
+    let count = 0
+    while (++count <= 17) {
+      publisher.inStream.write({
+        cmd: 'publish',
+        topic: 'hello',
+        payload: 'message-' + count,
+        qos: 1,
+        messageId: 42 + count
+      })
+    }
+    publisher.outStream.once('data', function (packet) {
+      t.equal(packet.cmd, 'puback')
+
+      subscriber = connect(setup(broker), opts)
+
+      const expected = [
+        [43, 'message-1'],
+        [44, 'message-2'],
+        [45, 'message-3'],
+        [46, 'message-4'],
+        [47, 'message-5'],
+        [48, 'message-6'],
+        [49, 'message-7'],
+        [50, 'message-8'],
+        [51, 'message-9'],
+        [52, 'message-10'],
+        [53, 'message-11'],
+        [54, 'message-12'],
+        [55, 'message-13'],
+        [56, 'message-14'],
+        [57, 'message-15'],
+        [58, 'message-16'],
+        [59, 'message-17']
+      ]
+
+      let recievedCount = 0
+      subscriber.outStream.on('data', function (packet) {
+        subscriber.inStream.write({
+          cmd: 'puback',
+          messageId: packet.messageId
+        })
+
+        const [messageId, payload] = expected[recievedCount++]
+
+        t.notEqual(packet.messageId, messageId, 'messageId should not match')
+        t.deepEqual(packet.payload, Buffer.from(payload), 'payload should match')
+      })
+    })
+  })
+})
+
 test('do not resend QoS 1 packets at each reconnect', function (t) {
   t.plan(6)