diff --git a/bifromq-mqtt/bifromq-mqtt-server/src/main/java/org/apache/bifromq/mqtt/handler/MQTTSessionHandler.java b/bifromq-mqtt/bifromq-mqtt-server/src/main/java/org/apache/bifromq/mqtt/handler/MQTTSessionHandler.java
index 97c859075..9811fea04 100644
--- a/bifromq-mqtt/bifromq-mqtt-server/src/main/java/org/apache/bifromq/mqtt/handler/MQTTSessionHandler.java
+++ b/bifromq-mqtt/bifromq-mqtt-server/src/main/java/org/apache/bifromq/mqtt/handler/MQTTSessionHandler.java
@@ -897,12 +897,14 @@ private void confirm(ConfirmingMessage confirmingMsg, boolean delivered) {
         long now = sessionCtx.nanoTime();
         confirmingMsg.setAcked();
         Iterator<Integer> packetIdItr = unconfirmedPacketIds.keySet().iterator();
+        boolean anyConfirmed = false;
         while (packetIdItr.hasNext()) {
             int packetId = packetIdItr.next();
             ConfirmingMessage head = unconfirmedPacketIds.get(packetId);
             if (head.acked) {
                 packetIdItr.remove();
                 confirmingMsg = head;
+                anyConfirmed = true;
                 long lastSentTimestamp = head.resendTimestamp > 0 ? head.resendTimestamp : head.timestamp;
                 RoutedMessage confirmed = confirmingMsg.message;
                 switch (confirmed.qos()) {
@@ -958,8 +960,12 @@ private void confirm(ConfirmingMessage confirmingMsg, boolean delivered) {
                 break;
             }
         }
-        // confirm up to the current seq
-        onConfirm(confirmingMsg.seq);
+        // confirm up to the last contiguously acknowledged seq; if the head of the
+        // window is still unacknowledged nothing is confirmed, so the watermark must
+        // not advance past it
+        if (anyConfirmed) {
+            onConfirm(confirmingMsg.seq);
+        }
     }
 
     protected abstract void onConfirm(long seq);
diff --git a/bifromq-mqtt/bifromq-mqtt-server/src/test/java/org/apache/bifromq/mqtt/handler/v3/MQTT3PersistentSessionHandlerTest.java b/bifromq-mqtt/bifromq-mqtt-server/src/test/java/org/apache/bifromq/mqtt/handler/v3/MQTT3PersistentSessionHandlerTest.java
index 806fa2aa4..b051c544a 100644
--- a/bifromq-mqtt/bifromq-mqtt-server/src/test/java/org/apache/bifromq/mqtt/handler/v3/MQTT3PersistentSessionHandlerTest.java
+++ b/bifromq-mqtt/bifromq-mqtt-server/src/test/java/org/apache/bifromq/mqtt/handler/v3/MQTT3PersistentSessionHandlerTest.java
@@ -42,10 +42,12 @@
 import static org.apache.bifromq.type.QoS.EXACTLY_ONCE;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.ArgumentMatchers.argThat;
+import static org.mockito.Mockito.never;
 import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
 import static org.mockito.Mockito.when;
 import static org.testng.Assert.assertEquals;
+import static org.testng.Assert.assertNotNull;
 import static org.testng.Assert.assertNull;
 import static org.testng.Assert.assertTrue;
 
@@ -477,6 +479,35 @@ public void qoS1PubAndNotAllAck() {
         verify(inboxClient, times(0)).commit(argThat(CommitRequest::hasSendBufferUpToSeq));
     }
 
+    @Test
+    public void outOfOrderPubAckMustNotAdvanceInboxWatermark() {
+        // #286: PUBACK carries no ordering requirement — a client may acknowledge
+        // packetId 2 while packetId 1 is still in flight. Confirming the inbox
+        // watermark up to the second message's seq would delete the un-acked first
+        // message from the inbox (permanent loss on session resume).
+        mockCheckPermission(true);
+        mockInboxCommit(CommitReply.Code.OK);
+        inboxFetchConsumer.accept(fetch(2, 128, QoS.AT_LEAST_ONCE));
+        channel.runPendingTasks();
+        MqttPublishMessage first = channel.readOutbound();
+        MqttPublishMessage second = channel.readOutbound();
+        assertNotNull(first);
+        assertNotNull(second);
+        // PUBACK the SECOND message only — the head (first) is still un-acked
+        channel.writeInbound(MQTTMessageUtils.pubAckMessage(second.variableHeader().packetId()));
+        channel.runPendingTasks();
+        // nothing was contiguously confirmed -> the watermark must not advance
+        verify(inboxClient, never()).commit(argThat(CommitRequest::hasSendBufferUpToSeq));
+
+        // phase 2: PUBACK the first — the delayed contiguous confirmation must now
+        // drain both acked entries and advance the watermark past the second message
+        channel.writeInbound(MQTTMessageUtils.pubAckMessage(first.variableHeader().packetId()));
+        channel.runPendingTasks();
+        verify(inboxClient, times(1)).commit(argThat(req ->
+            req.hasSendBufferUpToSeq() && req.getSendBufferUpToSeq() >= 1));
+        assertTrue(channel.isOpen());
+    }
+
     @Test
     public void qoS1PubAuthFailed() {
         // not by pass