diff --git a/docs/ReleaseNotes.md b/docs/ReleaseNotes.md
index d1cd9e7cb..dd5d92f83 100644
--- a/docs/ReleaseNotes.md
+++ b/docs/ReleaseNotes.md
@@ -8,6 +8,7 @@ Current package versions:
 
 ## Unreleased
 
+- Fix [#2392](https://github.com/StackExchange/StackExchange.Redis/issues/2392): Dequeue *all* timed out messages from the backlog when not connected (including Fire+Forget) ([#2397 by kornelpal](https://github.com/StackExchange/StackExchange.Redis/pull/2397))
 - Fix [#2400](https://github.com/StackExchange/StackExchange.Redis/issues/2400): Expose `ChannelMessageQueue` as `IAsyncEnumerable<ChannelMessage>` ([#2402 by mgravell](https://github.com/StackExchange/StackExchange.Redis/pull/2402))
 - Add: support for `CLIENT SETINFO` (lib name/version) during handshake; opt-out is via `ConfigurationOptions`; also support read of `resp`, `lib-ver` and `lib-name` via `CLIENT LIST` ([#2414 by mgravell](https://github.com/StackExchange/StackExchange.Redis/pull/2414))
 
diff --git a/src/StackExchange.Redis/PhysicalBridge.cs b/src/StackExchange.Redis/PhysicalBridge.cs
index efcd6518f..7fa8af27f 100644
--- a/src/StackExchange.Redis/PhysicalBridge.cs
+++ b/src/StackExchange.Redis/PhysicalBridge.cs
@@ -869,14 +869,14 @@ private void CheckBacklogForTimeouts()
             while (_backlog.TryPeek(out Message? message))
             {
                 // See if the message has pass our async timeout threshold
-                // or has otherwise been completed (e.g. a sync wait timed out) which would have cleared the ResultBox
-                if (!message.HasTimedOut(now, timeout, out var _) || message.ResultBox == null) break; // not a timeout - we can stop looking
+                // Note: All timed out messages must be dequeued, even when no completion is needed, to be able to dequeue and complete other timed out messages.
+                if (!message.HasTimedOut(now, timeout, out var _)) break; // not a timeout - we can stop looking
                 lock (_backlog)
                 {
                     // Peek again since we didn't have lock before...
                     // and rerun the exact same checks as above, note that it may be a different message now
                     if (!_backlog.TryPeek(out message)) break;
-                    if (!message.HasTimedOut(now, timeout, out var _) && message.ResultBox != null) break;
+                    if (!message.HasTimedOut(now, timeout, out var _)) break;
 
                     if (!BacklogTryDequeue(out var message2) || (message != message2)) // consume it for real
                     {
@@ -884,10 +884,15 @@ private void CheckBacklogForTimeouts()
                     }
                 }
 
-                // Tell the message it has failed
-                // Note: Attempting to *avoid* reentrancy/deadlock issues by not holding the lock while completing messages.
-                var ex = Multiplexer.GetException(WriteResult.TimeoutBeforeWrite, message, ServerEndPoint);
-                message.SetExceptionAndComplete(ex, this);
+                // We only handle async timeouts here, synchronous timeouts are handled upstream.
+                // Those sync timeouts happen in ConnectionMultiplexer.ExecuteSyncImpl() via Monitor.Wait.
+                if (message.ResultBoxIsAsync)
+                {
+                    // Tell the message it has failed
+                    // Note: Attempting to *avoid* reentrancy/deadlock issues by not holding the lock while completing messages.
+                    var ex = Multiplexer.GetException(WriteResult.TimeoutBeforeWrite, message, ServerEndPoint);
+                    message.SetExceptionAndComplete(ex, this);
+                }
             }
         }
 
diff --git a/tests/StackExchange.Redis.Tests/Issues/Issue2392Tests.cs b/tests/StackExchange.Redis.Tests/Issues/Issue2392Tests.cs
new file mode 100644
index 000000000..fe3e9673d
--- /dev/null
+++ b/tests/StackExchange.Redis.Tests/Issues/Issue2392Tests.cs
@@ -0,0 +1,46 @@
+using System;
+using System.Threading.Tasks;
+using Xunit;
+using Xunit.Abstractions;
+
+namespace StackExchange.Redis.Tests.Issues
+{
+    public class Issue2392Tests : TestBase
+    {
+        public Issue2392Tests(ITestOutputHelper output) : base(output) { }
+
+        [Fact]
+        public async Task Execute()
+        {
+            var options = new ConfigurationOptions()
+            {
+                BacklogPolicy = new()
+                {
+                    QueueWhileDisconnected = true,
+                    AbortPendingOnConnectionFailure = false,
+                },
+                AbortOnConnectFail = false,
+                ConnectTimeout = 1,
+                ConnectRetry = 0,
+                AsyncTimeout = 1,
+                SyncTimeout = 1,
+                AllowAdmin = true,
+            };
+            options.EndPoints.Add("127.0.0.1:1234");
+
+            using var conn = await ConnectionMultiplexer.ConnectAsync(options, Writer);
+            var key = Me();
+            var db = conn.GetDatabase();
+            var server = conn.GetServerSnapshot()[0];
+
+            // Fail the connection
+            conn.AllowConnect = false;
+            server.SimulateConnectionFailure(SimulatedFailureType.All);
+            Assert.False(conn.IsConnected);
+
+            await db.StringGetAsync(key, flags: CommandFlags.FireAndForget);
+            var ex = await Assert.ThrowsAnyAsync<Exception>(() => db.StringGetAsync(key).WithTimeout(5000));
+            Assert.True(ex is RedisTimeoutException or RedisConnectionException);
+        }
+    }
+}