diff --git a/src/Tools/Orchard/Host/CommandHost.cs b/src/Tools/Orchard/Host/CommandHost.cs
index ac3735f1d..7f6d58c9a 100644
--- a/src/Tools/Orchard/Host/CommandHost.cs
+++ b/src/Tools/Orchard/Host/CommandHost.cs
@@ -28,9 +28,9 @@ namespace Orchard.Host {
             HostingEnvironment.UnregisterObject(this);
         }
 
-        public void StartSession(TextReader input, TextWriter output) {
+        public int StartSession(TextReader input, TextWriter output) {
             _agent = CreateAgent();
-            StartHost(_agent, input, output);
+            return StartHost(_agent, input, output);
         }
 
         public void StopSession(TextReader input, TextWriter output) {
diff --git a/src/Tools/OrchardCli/CLIHost.cs b/src/Tools/OrchardCli/CLIHost.cs
index eed4be53a..d605bc890 100644
--- a/src/Tools/OrchardCli/CLIHost.cs
+++ b/src/Tools/OrchardCli/CLIHost.cs
@@ -17,8 +17,8 @@ namespace OrchardCLI {
         }
 
         public int Run() {
-            var context = _commandHostContextProvider.CreateContext();
-
+            var context = CommandHostContext();
+            Console.WriteLine("Type \"help commands\" for help, \"exit\" to exit");
             while (true) {
                 var command = ReadCommand(context);
                 switch (command.ToLowerInvariant()) {
@@ -41,12 +41,24 @@ namespace OrchardCLI {
             return Console.ReadLine();
         }
 
+        private CommandHostContext CommandHostContext() {
+            Console.WriteLine("Initializing Orchard session... (This might take a few seconds)");
+            var result = _commandHostContextProvider.CreateContext();
+            if (result.StartSessionResult == 240/*special return code for "Retry"*/) {
+                result = _commandHostContextProvider.CreateContext();
+            }
+            return result;
+        }
+
         private CommandHostContext RunCommand(CommandHostContext context, string command) {
+            if (string.IsNullOrWhiteSpace(command))
+                return context;
+
             int result = RunCommandInSession(context, command);
             if(result == 240) {
                 if (result == 240/*special return code for "Retry"*/) {
                     _commandHostContextProvider.Shutdown(context);
-                    context = _commandHostContextProvider.CreateContext();
+                    context = CommandHostContext();
                     result = RunCommandInSession(context, command);
                     if (result != 0)
                         Console.WriteLine("Command returned non-zero result: {0}", result);
diff --git a/src/Tools/OrchardCli/CommandHostContext.cs b/src/Tools/OrchardCli/CommandHostContext.cs
index b716caf73..d3cf36e84 100644
--- a/src/Tools/OrchardCli/CommandHostContext.cs
+++ b/src/Tools/OrchardCli/CommandHostContext.cs
@@ -6,6 +6,7 @@ using Orchard.Host;
 
 namespace OrchardCLI {
     public class CommandHostContext {
+        public int StartSessionResult { get; set; }
         public OrchardParameters Arguments { get; set; }
         public DirectoryInfo OrchardDirectory { get; set; }
         public ApplicationManager AppManager { get; set; }
diff --git a/src/Tools/OrchardCli/CommandHostContextProvider.cs b/src/Tools/OrchardCli/CommandHostContextProvider.cs
index 038ccd973..d883221a3 100644
--- a/src/Tools/OrchardCli/CommandHostContextProvider.cs
+++ b/src/Tools/OrchardCli/CommandHostContextProvider.cs
@@ -9,7 +9,7 @@ using Orchard.Host;
 using Orchard.Parameters;
 
 namespace OrchardCLI {
-    public class CommandHostContextProvider : ICommandHostContextProvider{
+    public class CommandHostContextProvider : ICommandHostContextProvider {
         private readonly string[] _args;
         private TextWriter _output;
         private TextReader _input;
@@ -27,7 +27,20 @@ namespace OrchardCLI {
         }
 
         public void Shutdown(CommandHostContext context) {
-            ShutdownHost(context);
+            try {
+                if (context.CommandHost != null) {
+                    LogInfo(context, "Shutting down Orchard session...");
+                    context.CommandHost.StopSession(_input, _output);
+                }
+            }
+            catch (AppDomainUnloadedException) {
+                LogInfo(context, "   (AppDomain already unloaded)");
+            }
+
+            if (context.AppObject != null) {
+                LogInfo(context, "Shutting down ASP.NET AppDomain...");
+                context.AppManager.ShutdownApplication(context.AppObject.ApplicationId);
+            }
         }
 
         private void Initialize(CommandHostContext context) {
@@ -64,27 +77,13 @@ namespace OrchardCLI {
             context.OrchardDirectory = GetOrchardDirectory(context.Arguments.WorkingDirectory);
             LogInfo(context, "Orchard root directory: \"{0}\"", context.OrchardDirectory.FullName);
 
-            CreateHost(context);
-            context.CommandHost.StartSession(_input, _output);
-        }
-
-        private void CreateHost(CommandHostContext context) {
-            context.AppManager = ApplicationManager.GetApplicationManager();
-
             LogInfo(context, "Creating ASP.NET AppDomain for command agent...");
+            context.AppManager = ApplicationManager.GetApplicationManager();
             context.AppObject = CreateWorkerAppDomainWithHost(context.AppManager, context.Arguments.VirtualPath, context.OrchardDirectory.FullName, typeof(CommandHost));
             context.CommandHost = (CommandHost)context.AppObject.ObjectInstance;
-        }
 
-        private void ShutdownHost(CommandHostContext context) {
-            if (context.CommandHost != null) {
-                context.CommandHost.StopSession(_input, _output);
-            }
-
-            if (context.AppObject != null) {
-                LogInfo(context, "Shutting down ASP.NET AppDomain...");
-                context.AppManager.ShutdownApplication(context.AppObject.ApplicationId);
-            }
+            LogInfo(context, "Starting Orchard session");
+            context.StartSessionResult = context.CommandHost.StartSession(_input, _output);
         }
 
         private int GeneralHelp() {