diff --git a/src/SOS/SOS.UnitTests/SOSRunner.cs b/src/SOS/SOS.UnitTests/SOSRunner.cs
index 4d92aff541..647bb08fb7 100644
--- a/src/SOS/SOS.UnitTests/SOSRunner.cs
+++ b/src/SOS/SOS.UnitTests/SOSRunner.cs
@@ -378,9 +378,10 @@ public static async Task<string> CreateDump(TestInformation information)
                         if (pipeServer != null)
                         {
                             dotnetDumpOutputHelper.WriteLine("Waiting for connection on pipe {0}", pipeName);
-                            CancellationTokenSource source = new(TimeSpan.FromMinutes(5));
+                            using CancellationTokenSource source = new(TimeSpan.FromMinutes(5));
 
                             // Wait for debuggee to connect/write to pipe or if the process exits on some other failure/abnormally
+                            // TODO: This is a resiliency issue - we'll try to collect the dump even if the debuggee fails to connect.
                             await Task.WhenAny(pipeServer.WaitForConnectionAsync(source.Token), processRunner.WaitForExit());
                         }
 
diff --git a/src/tests/CommonTestRunner/TestRunner.cs b/src/tests/CommonTestRunner/TestRunner.cs
index a552385a6a..730dac25d1 100644
--- a/src/tests/CommonTestRunner/TestRunner.cs
+++ b/src/tests/CommonTestRunner/TestRunner.cs
@@ -245,8 +245,16 @@ public async Task WaitForTracee()
                 WriteLine("WaitForTracee");
                 try
                 {
-                    CancellationTokenSource source = new(TimeSpan.FromMinutes(2));
-                    await _pipeServer.WaitForConnectionAsync(source.Token).ConfigureAwait(false);
+                    using CancellationTokenSource source = new(TimeSpan.FromMinutes(2));
+                    Task processDeath = _runner.WaitForExit();
+                    Task traceeReady = _pipeServer.WaitForConnectionAsync(source.Token);
+                    Task doneTask = await Task.WhenAny(processDeath, traceeReady).WaitAsync(source.Token).ConfigureAwait(false);
+
+                    source.Cancel();
+                    if (doneTask == processDeath)
+                    {
+                        Trace.TraceWarning($"WaitForTracee: process {Pid} exited without sending the event");
+                    }
                     WriteLine("WaitForTracee: DONE");
                 }
                 catch (Exception ex) when (ex is TaskCanceledException or OperationCanceledException)
diff --git a/src/tests/DbgShim.UnitTests/DebuggeeInfo.cs b/src/tests/DbgShim.UnitTests/DebuggeeInfo.cs
index b60e30ed6c..48588a6c64 100644
--- a/src/tests/DbgShim.UnitTests/DebuggeeInfo.cs
+++ b/src/tests/DbgShim.UnitTests/DebuggeeInfo.cs
@@ -71,9 +71,21 @@ public async Task<bool> WaitForDebuggee()
             }
             try
             {
-                CancellationTokenSource source = new(TimeSpan.FromMinutes(5));
+                using CancellationTokenSource source = new(TimeSpan.FromMinutes(5));
                 Trace.TraceInformation($"DebuggeeInfo.WaitForDebuggee: waiting {ProcessId}");
-                await _pipeServer.WaitForConnectionAsync(source.Token);
+
+                Task processDeath = _process.WaitForExitAsync(source.Token);
+                Task debuggeeReady = _pipeServer.WaitForConnectionAsync(source.Token);
+                Task doneTask = await Task.WhenAny(processDeath, debuggeeReady).WaitAsync(source.Token);
+
+                source.Cancel();
+
+                if (doneTask == processDeath)
+                {
+                    Trace.TraceWarning($"DebuggeeInfo.WaitForDebuggee: process {ProcessId} exited");
+                    return false;
+                }
+
                 Trace.TraceInformation($"DebuggeeInfo.WaitForDebuggee: after wait {ProcessId}");
             }
             catch (Exception ex) when (ex is TaskCanceledException or OperationCanceledException)