diff --git a/src/Runner.Worker/Dap/DapDebugger.cs b/src/Runner.Worker/Dap/DapDebugger.cs
index ec3adaf3e..5f5214dac 100644
--- a/src/Runner.Worker/Dap/DapDebugger.cs
+++ b/src/Runner.Worker/Dap/DapDebugger.cs
@@ -1320,6 +1320,13 @@ namespace GitHub.Runner.Worker.Dap
                 _commandTcs = new TaskCompletionSource<DapCommand>(TaskCreationOptions.RunContinuationsAsynchronously);
             }
 
+            // If cancellation already fired before we created the new TCS,
+            // the registration callback targeted the old one. Unblock now.
+            if (cancellationToken.IsCancellationRequested)
+            {
+                _commandTcs.TrySetResult(DapCommand.Disconnect);
+            }
+
             Trace.Info("Waiting for debugger command...");
 
             var command = await _commandTcs.Task;
diff --git a/src/Runner.Worker/JobExtension.cs b/src/Runner.Worker/JobExtension.cs
index 991e4b37b..bf451ce99 100644
--- a/src/Runner.Worker/JobExtension.cs
+++ b/src/Runner.Worker/JobExtension.cs
@@ -550,6 +550,21 @@ namespace GitHub.Runner.Worker
                 }
                 finally
                 {
+                    // If InitializeJob failed after the debugger was started,
+                    // clean it up here since FinalizeJob won't run.
+                    if (context.Result != null && _dapDebugger != null)
+                    {
+                        try
+                        {
+                            await _dapDebugger.OnJobCompletedAsync();
+                        }
+                        catch (Exception ex)
+                        {
+                            Trace.Warning($"DAP debugger cleanup during failed init: {ex.Message}");
+                        }
+                        _dapDebugger = null;
+                    }
+
                     context.Debug("Finishing: Set up job");
                     context.Complete();
                 }
diff --git a/src/Test/L0/Worker/DapDebuggerL0.cs b/src/Test/L0/Worker/DapDebuggerL0.cs
index 9454b1a3a..2d1ac596b 100644
--- a/src/Test/L0/Worker/DapDebuggerL0.cs
+++ b/src/Test/L0/Worker/DapDebuggerL0.cs
@@ -744,14 +744,32 @@ namespace GitHub.Runner.Common.Tests.Worker
                 await ReadDapMessageAsync(stream, TimeSpan.FromSeconds(5));
                 await waitTask;
 
-                // Complete the job — events are sent via OnJobCompletedAsync
-                await _debugger.OnJobCompletedAsync();
+                // Complete the job — OnJobCompletedAsync pauses when stepping,
+                // so run it in the background and send continue to unblock.
+                var completedTask = _debugger.OnJobCompletedAsync();
 
-                var msg1 = await ReadDapMessageAsync(stream, TimeSpan.FromSeconds(5));
-                var msg2 = await ReadDapMessageAsync(stream, TimeSpan.FromSeconds(5));
+                // Read the stopped event from the pause
+                var stoppedMsg = await ReadDapMessageAsync(stream, TimeSpan.FromSeconds(5));
+                Assert.Contains("\"event\":\"stopped\"", stoppedMsg);
 
-                // Both events should arrive (order may vary)
-                var combined = msg1 + msg2;
+                // Send continue to unblock the pause
+                await SendRequestAsync(stream, new Request
+                {
+                    Seq = 2,
+                    Type = "request",
+                    Command = "continue"
+                });
+
+                await completedTask;
+
+                // Read remaining messages — continue response + continued event + terminated + exited
+                var allMessages = new System.Text.StringBuilder();
+                for (int i = 0; i < 4; i++)
+                {
+                    allMessages.Append(await ReadDapMessageAsync(stream, TimeSpan.FromSeconds(5)));
+                }
+
+                var combined = allMessages.ToString();
                 Assert.Contains("\"event\":\"terminated\"", combined);
                 Assert.Contains("\"event\":\"exited\"", combined);
             }