diff --git a/test/DeploymentHelpers/Common/RetryHelper.cs b/test/DeploymentHelpers/Common/RetryHelper.cs
index ddae86ecfe..01d515d709 100644
--- a/test/DeploymentHelpers/Common/RetryHelper.cs
+++ b/test/DeploymentHelpers/Common/RetryHelper.cs
@@ -28,6 +28,7 @@ namespace DeploymentHelpers
                 {
                     if (cancellationToken.IsCancellationRequested)
                     {
+                        logger.LogInformation("Stopping retry as cancellation token is triggered.");
                         break;
                     }
 
diff --git a/test/DeploymentHelpers/Deployers/IISExpressDeployer.cs b/test/DeploymentHelpers/Deployers/IISExpressDeployer.cs
index 1e3ba2d89e..8119eff4e9 100644
--- a/test/DeploymentHelpers/Deployers/IISExpressDeployer.cs
+++ b/test/DeploymentHelpers/Deployers/IISExpressDeployer.cs
@@ -102,6 +102,7 @@ namespace DeploymentHelpers
 #endif
 
             _hostProcess = Process.Start(startInfo);
+            _hostProcess.EnableRaisingEvents = true;
             var hostExitTokenSource = new CancellationTokenSource();
             _hostProcess.Exited += (sender, e) =>
             {
diff --git a/test/DeploymentHelpers/Deployers/MonoDeployer.cs b/test/DeploymentHelpers/Deployers/MonoDeployer.cs
index 7917e86e7e..f32600b8a7 100644
--- a/test/DeploymentHelpers/Deployers/MonoDeployer.cs
+++ b/test/DeploymentHelpers/Deployers/MonoDeployer.cs
@@ -72,6 +72,7 @@ namespace DeploymentHelpers
             };
 
             _hostProcess = Process.Start(startInfo);
+            _hostProcess.EnableRaisingEvents = true;
             var hostExitTokenSource = new CancellationTokenSource();
             _hostProcess.Exited += (sender, e) =>
             {
diff --git a/test/DeploymentHelpers/Deployers/SelfHostDeployer.cs b/test/DeploymentHelpers/Deployers/SelfHostDeployer.cs
index 2623c4ddff..d890dc9ee2 100644
--- a/test/DeploymentHelpers/Deployers/SelfHostDeployer.cs
+++ b/test/DeploymentHelpers/Deployers/SelfHostDeployer.cs
@@ -58,6 +58,7 @@ namespace DeploymentHelpers
             AddEnvironmentVariablesToProcess(startInfo);
 
             _hostProcess = Process.Start(startInfo);
+            _hostProcess.EnableRaisingEvents = true;
             var hostExitTokenSource = new CancellationTokenSource();
             _hostProcess.Exited += (sender, e) =>
             {