diff --git a/src/StackExchange.Redis/PhysicalBridge.cs b/src/StackExchange.Redis/PhysicalBridge.cs
index 7cf39edeb..eb81a8170 100644
--- a/src/StackExchange.Redis/PhysicalBridge.cs
+++ b/src/StackExchange.Redis/PhysicalBridge.cs
@@ -193,17 +193,18 @@ private WriteResult QueueOrFailMessage(Message message)
             }
 
             // Anything else goes in the bin - we're just not ready for you yet
-            message.Cancel();
-            Multiplexer.OnMessageFaulted(message, null);
-            message.Complete(null);
-            return WriteResult.NoConnectionAvailable;
+            return FailDueToNoConnection(message);
         }
 
         private WriteResult FailDueToNoConnection(Message message)
         {
-            message.Cancel();
-            Multiplexer.OnMessageFaulted(message, null);
-            message.Complete(null);
+            // fail with the exception the caller would otherwise construct from the result, rather than Cancel():
+            // a cancelled box surfaces as TaskCanceledException, and although ExecuteAsyncImpl then tries to
+            // fault the task with the real exception, the box's continuation can get there first (#3283) - and a
+            // batch has no caller translating the result at all
+            var ex = ExceptionFactory.NoConnectionAvailable(Multiplexer, message, ServerEndPoint);
+            Multiplexer.OnMessageFaulted(message, ex);
+            message.SetExceptionAndComplete(ex, null);
             return WriteResult.NoConnectionAvailable;
         }
 
@@ -1368,9 +1369,10 @@ public bool HasPendingCallerFacingItems()
 
         private WriteResult TimedOutBeforeWrite(Message message)
         {
-            message.Cancel();
-            Multiplexer.OnMessageFaulted(message, null);
-            message.Complete(null);
+            // as FailDueToNoConnection: a real exception, not Cancel()
+            var ex = ExceptionFactory.Timeout(Multiplexer, null, message, ServerEndPoint, WriteResult.TimeoutBeforeWrite, this);
+            Multiplexer.OnMessageFaulted(message, ex);
+            message.SetExceptionAndComplete(ex, null);
             return WriteResult.TimeoutBeforeWrite;
         }
 
diff --git a/src/StackExchange.Redis/PhysicalConnection.cs b/src/StackExchange.Redis/PhysicalConnection.cs
index c960e4230..9e5eab6a1 100644
--- a/src/StackExchange.Redis/PhysicalConnection.cs
+++ b/src/StackExchange.Redis/PhysicalConnection.cs
@@ -696,6 +696,14 @@ void AddData(string? lk, string? sk, string? v)
             }
 
             var ex = innerException is RedisException ? innerException : outerException;
+            if (ex is not RedisException)
+            {
+                // the detailed exception above is built once, for the bridge's *current* connection; a repeat
+                // report for the same connection, or one the bridge has already replaced, must still fail
+                // whatever is queued - and with a RedisConnectionException, not the raw transport fault, nor
+                // (when there is no exception at all, e.g. EOF) a TaskCanceledException nobody asked for (#3283)
+                ex = new RedisConnectionException(failureType, CommandFlags.None, failureType + " on " + ToString(), innerException);
+            }
 
             nextMessage = Interlocked.Exchange(ref _awaitingToken, null);
             if (nextMessage is not null)
diff --git a/tests/StackExchange.Redis.Tests/ConnectionFailureExceptionTests.cs b/tests/StackExchange.Redis.Tests/ConnectionFailureExceptionTests.cs
new file mode 100644
index 000000000..79a8d84e1
--- /dev/null
+++ b/tests/StackExchange.Redis.Tests/ConnectionFailureExceptionTests.cs
@@ -0,0 +1,78 @@
+using System;
+using System.IO;
+using System.Threading.Tasks;
+using Xunit;
+
+namespace StackExchange.Redis.Tests;
+
+/// <summary>
+/// A command that fails because its connection failed must fail with a <see cref="RedisConnectionException"/>
+/// carrying the transport fault as its inner exception: never the raw transport exception, and never a
+/// <see cref="TaskCanceledException"/> when no caller token was involved (#3283).
+/// </summary>
+public class ConnectionFailureExceptionTests(ITestOutputHelper log)
+{
+    private static (Message Message, Task<bool> Task) CreateTrackedPing()
+    {
+        var message = Message.Create(-1, CommandFlags.None, RedisCommand.PING);
+        var box = TaskResultBox<bool>.Create(out var tcs, null);
+        message.SetSource(box, ResultProcessor.DemandOK);
+        return (message, tcs.Task);
+    }
+
+    private static async Task<Exception> AwaitFailure(Task task)
+    {
+        var completed = await Task.WhenAny(task, Task.Delay(TimeSpan.FromSeconds(10)));
+        Assert.Same(task, completed);
+        return await Assert.ThrowsAnyAsync<Exception>(() => task);
+    }
+
+    [Theory]
+    [InlineData(false)] // EOF-style report: no exception at all (used to surface as TaskCanceledException)
+    [InlineData(true)] // transport fault (used to surface raw when the detailed report was not built)
+    public async Task DrainedMessagesFailWithRedisConnectionException(bool withInner)
+    {
+        // a dummy connection has no bridge, so it is never the bridge's *current* connection and the detailed
+        // first-report exception is not built: this is exactly the path that handed out raw/null exceptions
+        using var stream = new MemoryStream();
+        using var connection = PhysicalConnection.Dummy(stream);
+        var (message, task) = CreateTrackedPing();
+        connection.EnqueueInsideWriteLock(message, enforceMuxer: false);
+
+        var inner = withInner ? new IOException("simulated transport fault") : null;
+        connection.RecordConnectionFailed(ConnectionFailureType.SocketClosed, inner);
+
+        var ex = await AwaitFailure(task);
+        log.WriteLine(ex.ToString());
+        var conn = Assert.IsType<RedisConnectionException>(ex);
+        Assert.Equal(ConnectionFailureType.SocketClosed, conn.FailureType);
+        Assert.Same(inner, conn.InnerException);
+    }
+
+    [Fact]
+    public async Task NoConnectionFailsWithRedisConnectionExceptionNotCancellation()
+    {
+        using var server = new InProcessTestServer(log);
+        var config = server.GetClientConfig(withPubSub: false, defaultOnly: true);
+        config.BacklogPolicy = BacklogPolicy.FailFast;
+        config.AbortOnConnectFail = false;
+        config.AllowSimulateConnectionFailure = true;
+        await using var conn = await ConnectionMultiplexer.ConnectAsync(config);
+        var endpoint = conn.GetServerSnapshot()[0];
+        var bridge = endpoint.GetBridge(ConnectionType.Interactive)!;
+
+        conn.AllowConnect = false;
+        endpoint.SimulateConnectionFailure(SimulatedFailureType.All);
+        Assert.False(conn.IsConnected);
+
+        // write at the bridge, so we observe the message's own outcome rather than the caller's translation of
+        // the write result (which is what hid this for single commands - most of the time)
+        var (message, task) = CreateTrackedPing();
+        Assert.Equal(WriteResult.NoConnectionAvailable, await bridge.TryWriteAsync(message, isReplica: false));
+
+        var ex = await AwaitFailure(task);
+        log.WriteLine(ex.ToString());
+        Assert.IsType<RedisConnectionException>(ex);
+        Assert.False(task.IsCanceled);
+    }
+}