diff --git a/src/Microsoft.Tye.Hosting/DockerRunner.cs b/src/Microsoft.Tye.Hosting/DockerRunner.cs
index f8a12460..a7a43a65 100644
--- a/src/Microsoft.Tye.Hosting/DockerRunner.cs
+++ b/src/Microsoft.Tye.Hosting/DockerRunner.cs
@@ -15,6 +15,7 @@ namespace Microsoft.Tye.Hosting
 {
     public class DockerRunner : IApplicationProcessor
     {
+        private static readonly TimeSpan DockerStopTimeout = TimeSpan.FromSeconds(30);
         private readonly ILogger _logger;
 
         public DockerRunner(ILogger logger)
@@ -207,12 +208,17 @@ namespace Microsoft.Tye.Hosting
                 _logger.LogInformation("docker logs collection for {ContainerName} complete with exit code {ExitCode}", replica, result.ExitCode);
 
                 // Docker has a tendency to get stuck so we're going to timeout this shutdown process
-                var timeoutCts = new CancellationTokenSource(TimeSpan.FromSeconds(5));
+                var timeoutCts = new CancellationTokenSource(DockerStopTimeout);
 
                 _logger.LogInformation("Stopping container {ContainerName} with ID {ContainerId}", replica, shortContainerId);
 
                 result = await ProcessUtil.RunAsync("docker", $"stop {containerId}", throwOnError: false, cancellationToken: timeoutCts.Token);
 
+                if (timeoutCts.IsCancellationRequested)
+                {
+                    _logger.LogWarning($"Failed to stop container after {DockerStopTimeout.Seconds} seconds, container will most likely be running.", replica, shortContainerId);
+                }
+
                 PrintStdOutAndErr(service, replica, result);
 
                 service.ReplicaEvents.OnNext(new ReplicaEvent(ReplicaState.Stopped, status));
@@ -221,6 +227,11 @@ namespace Microsoft.Tye.Hosting
 
                 result = await ProcessUtil.RunAsync("docker", $"rm {containerId}", throwOnError: false, cancellationToken: timeoutCts.Token);
 
+                if (timeoutCts.IsCancellationRequested)
+                {
+                    _logger.LogWarning($"Failed to remove container after {DockerStopTimeout.Seconds} seconds, container will most likely still exist.", replica, shortContainerId);
+                }
+
                 PrintStdOutAndErr(service, replica, result);
 
                 _logger.LogInformation("Removed container {ContainerName} with ID {ContainerId} exited with {ExitCode}", replica, shortContainerId, result.ExitCode);