diff --git a/module/PowerShellEditorServices/PowerShellEditorServices.psm1 b/module/PowerShellEditorServices/PowerShellEditorServices.psm1
index b37b6ee65..5861b9420 100644
--- a/module/PowerShellEditorServices/PowerShellEditorServices.psm1
+++ b/module/PowerShellEditorServices/PowerShellEditorServices.psm1
@@ -150,12 +150,12 @@ function Start-EditorServicesHost {
     }
 
     if ($DebugServiceOnly.IsPresent) {
-        $editorServicesHost.StartDebugService($debugServiceConfig, $profilePaths, $false);
+        $editorServicesHost.StartDebugService($debugServiceConfig, $profilePaths, $true);
     } elseif($Stdio.IsPresent) {
         $editorServicesHost.StartLanguageService($languageServiceConfig, $profilePaths);
     } else {
         $editorServicesHost.StartLanguageService($languageServiceConfig, $profilePaths);
-        $editorServicesHost.StartDebugService($debugServiceConfig, $profilePaths, $true);
+        $editorServicesHost.StartDebugService($debugServiceConfig, $profilePaths, $false);
     }
 
     return $editorServicesHost
diff --git a/src/PowerShellEditorServices/Hosting/EditorServicesHost.cs b/src/PowerShellEditorServices/Hosting/EditorServicesHost.cs
index fd14dd787..68c004c0c 100644
--- a/src/PowerShellEditorServices/Hosting/EditorServicesHost.cs
+++ b/src/PowerShellEditorServices/Hosting/EditorServicesHost.cs
@@ -21,6 +21,7 @@
 using Microsoft.PowerShell.EditorServices.Server;
 using Microsoft.PowerShell.EditorServices.Services;
 using Microsoft.PowerShell.EditorServices.Utility;
+using OmniSharp.Extensions.LanguageServer.Protocol.Server;
 using Serilog;
 
 namespace Microsoft.PowerShell.EditorServices.Hosting
@@ -284,14 +285,33 @@ public void StartLanguageService(
         /// </summary>
         /// <param name="config">The config that contains information on the communication protocol that will be used.</param>
         /// <param name="profilePaths">The profiles that will be loaded in the session.</param>
-        /// <param name="useExistingSession">Determines if we will reuse the session that we have.</param>
+        /// <param name="useTempSession">Determines if we will make a new session typically used for temporary console debugging.</param>
         public void StartDebugService(
             EditorServiceTransportConfig config,
             ProfilePaths profilePaths,
-            bool useExistingSession)
+            bool useTempSession)
         {
             _logger.LogInformation($"Debug NamedPipe: {config.InOutPipeName}\nDebug OutPipe: {config.OutPipeName}");
 
+            IServiceProvider serviceProvider = null;
+            if (useTempSession)
+            {
+                serviceProvider = new ServiceCollection()
+                    .AddLogging(builder => builder
+                        .ClearProviders()
+                        .AddSerilog()
+                        .SetMinimumLevel(LogLevel.Trace))
+                    .AddSingleton<ILanguageServer>(provider => null)
+                    .AddPsesLanguageServices(
+                        profilePaths,
+                        _featureFlags,
+                        _enableConsoleRepl,
+                        _internalHost,
+                        _hostDetails,
+                        _additionalModules)
+                    .BuildServiceProvider();
+            }
+
             switch (config.TransportType)
             {
                 case EditorServiceTransportType.NamedPipe:
@@ -312,7 +332,7 @@ public void StartDebugService(
                         .ContinueWith(async task =>
                         {
                             _logger.LogInformation("Starting debug server");
-                            await _debugServer.StartAsync(_languageServer.LanguageServer.Services);
+                            await _debugServer.StartAsync(serviceProvider ?? _languageServer.LanguageServer.Services, useTempSession);
                             _logger.LogInformation(
                                 $"Debug service started, type = {config.TransportType}, endpoint = {config.Endpoint}");
                         });
@@ -325,25 +345,11 @@ public void StartDebugService(
                         Console.OpenStandardInput(),
                         Console.OpenStandardOutput());
 
+                    _logger.LogInformation("Starting debug server");
                     Task.Run(async () =>
                     {
-                        _logger.LogInformation("Starting debug server");
-
-                        IServiceProvider serviceProvider = useExistingSession
-                            ? _languageServer.LanguageServer.Services
-                            : new ServiceCollection().AddSingleton<PowerShellContextService>(
-                                (provider) => PowerShellContextService.Create(
-                                    _factory,
-                                    provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>(),
-                                    profilePaths,
-                                    _featureFlags,
-                                    _enableConsoleRepl,
-                                    _internalHost,
-                                    _hostDetails,
-                                    _additionalModules))
-                                .BuildServiceProvider();
-
-                        await _debugServer.StartAsync(serviceProvider);
+
+                        await _debugServer.StartAsync(serviceProvider ?? _languageServer.LanguageServer.Services, useTempSession);
                         _logger.LogInformation(
                             $"Debug service started, type = {config.TransportType}, endpoint = {config.Endpoint}");
                     });
@@ -353,14 +359,19 @@ public void StartDebugService(
                     throw new NotSupportedException($"The transport {config.TransportType} is not supported");
             }
 
-            if(!alreadySubscribedDebug)
+            // If the instance of PSES is being used for debugging only, then we don't want to allow automatic restarting
+            // because the user can simply spin up a new PSES if they need to.
+            // This design decision was done since this "debug-only PSES" is used in the "Temporary Integrated Console debugging"
+            // feature which does not want PSES to be restarted so that the user can see the output of the last debug
+            // session.
+            if(!alreadySubscribedDebug && !useTempSession)
             {
                 alreadySubscribedDebug = true;
                 _debugServer.SessionEnded += (sender, eventArgs) =>
                 {
                     _debugServer.Dispose();
                     alreadySubscribedDebug = false;
-                    StartDebugService(config, profilePaths, useExistingSession);
+                    StartDebugService(config, profilePaths, useTempSession);
                 };
             }
         }
@@ -378,8 +389,20 @@ public void StopServices()
         /// </summary>
         public void WaitForCompletion()
         {
-            // TODO: We need a way to know when to complete this task!
-            _languageServer.WaitForShutdown().Wait();
+            // If _languageServer is not null, then we are either using:
+            // Stdio - that only uses a LanguageServer so we return when that has shutdown.
+            // NamedPipes - that uses both LanguageServer and DebugServer, but LanguageServer
+            //              is the core of PowerShell Editor Services and if that shuts down,
+            //              we want the whole process to shutdown.
+            if (_languageServer != null)
+            {
+                _languageServer.WaitForShutdown().GetAwaiter().GetResult();
+                return;
+            }
+
+            // If there is no LanguageServer, then we must be running with the DebugServiceOnly switch
+            // (used in Temporary console debugging) and we need to wait for the DebugServer to shutdown.
+            _debugServer.WaitForShutdown().GetAwaiter().GetResult();
         }
 
         #endregion
diff --git a/src/PowerShellEditorServices/Server/PsesDebugServer.cs b/src/PowerShellEditorServices/Server/PsesDebugServer.cs
index 860dbc845..98474b0be 100644
--- a/src/PowerShellEditorServices/Server/PsesDebugServer.cs
+++ b/src/PowerShellEditorServices/Server/PsesDebugServer.cs
@@ -26,6 +26,8 @@ public class PsesDebugServer : IDisposable
 
         private PowerShellContextService _powerShellContextService;
 
+        private readonly TaskCompletionSource<bool> _serverStopped;
+
         public PsesDebugServer(
             ILoggerFactory factory,
             Stream inputStream,
@@ -34,9 +36,10 @@ public PsesDebugServer(
             _loggerFactory = factory;
             _inputStream = inputStream;
             _outputStream = outputStream;
+            _serverStopped = new TaskCompletionSource<bool>();
         }
 
-        public async Task StartAsync(IServiceProvider languageServerServiceProvider)
+        public async Task StartAsync(IServiceProvider languageServerServiceProvider, bool useTempSession)
         {
             _jsonRpcServer = await JsonRpcServer.From(options =>
             {
@@ -50,14 +53,13 @@ public async Task StartAsync(IServiceProvider languageServerServiceProvider)
                 _powerShellContextService = languageServerServiceProvider.GetService<PowerShellContextService>();
                 _powerShellContextService.IsDebugServerActive = true;
 
+                // Needed to make sure PSReadLine's static properties are initialized in the pipeline thread.
+                _powerShellContextService
+                    .ExecuteScriptStringAsync("[System.Runtime.CompilerServices.RuntimeHelpers]::RunClassConstructor([Microsoft.PowerShell.PSConsoleReadLine].TypeHandle)")
+                    .Wait();
+
                 options.Services = new ServiceCollection()
-                    .AddSingleton(_powerShellContextService)
-                    .AddSingleton(languageServerServiceProvider.GetService<WorkspaceService>())
-                    .AddSingleton(languageServerServiceProvider.GetService<RemoteFileManagerService>())
-                    .AddSingleton<PsesDebugServer>(this)
-                    .AddSingleton<DebugService>()
-                    .AddSingleton<DebugStateService>()
-                    .AddSingleton<DebugEventHandlerService>();
+                    .AddPsesDebugServices(languageServerServiceProvider, this, useTempSession);
 
                 options
                     .WithInput(_inputStream)
@@ -95,6 +97,12 @@ public void Dispose()
         {
             _powerShellContextService.IsDebugServerActive = false;
             _jsonRpcServer.Dispose();
+            _serverStopped.SetResult(true);
+        }
+
+        public async Task WaitForShutdown()
+        {
+            await _serverStopped.Task;
         }
 
         #region Events
diff --git a/src/PowerShellEditorServices/Server/PsesLanguageServer.cs b/src/PowerShellEditorServices/Server/PsesLanguageServer.cs
index 3d6901479..caddc5e5f 100644
--- a/src/PowerShellEditorServices/Server/PsesLanguageServer.cs
+++ b/src/PowerShellEditorServices/Server/PsesLanguageServer.cs
@@ -65,43 +65,13 @@ public async Task StartAsync()
                     .WithInput(input)
                     .WithOutput(output)
                     .WithServices(serviceCollection => serviceCollection
-                        .AddSingleton<WorkspaceService>()
-                        .AddSingleton<SymbolsService>()
-                        .AddSingleton<ConfigurationService>()
-                        .AddSingleton<PowerShellContextService>(
-                            (provider) =>
-                                PowerShellContextService.Create(
-                                    provider.GetService<ILoggerFactory>(),
-                                    provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>(),
-                                    _profilePaths,
-                                    _featureFlags,
-                                    _enableConsoleRepl,
-                                    _internalHost,
-                                    _hostDetails,
-                                    _additionalModules))
-                        .AddSingleton<TemplateService>()
-                        .AddSingleton<EditorOperationsService>()
-                        .AddSingleton<RemoteFileManagerService>()
-                        .AddSingleton<ExtensionService>(
-                            (provider) =>
-                            {
-                                var extensionService = new ExtensionService(
-                                    provider.GetService<PowerShellContextService>(),
-                                    provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>());
-                                extensionService.InitializeAsync(
-                                    serviceProvider: provider,
-                                    editorOperations: provider.GetService<EditorOperationsService>())
-                                    .Wait();
-                                return extensionService;
-                            })
-                        .AddSingleton<AnalysisService>(
-                            (provider) =>
-                            {
-                                return AnalysisService.Create(
-                                    provider.GetService<ConfigurationService>(),
-                                    provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>(),
-                                    provider.GetService<ILoggerFactory>().CreateLogger<AnalysisService>());
-                            }))
+                        .AddPsesLanguageServices(
+                            _profilePaths,
+                            _featureFlags,
+                            _enableConsoleRepl,
+                            _internalHost,
+                            _hostDetails,
+                            _additionalModules))
                     .ConfigureLogging(builder => builder
                         .AddSerilog(Log.Logger)
                         .SetMinimumLevel(LogLevel.Trace))
diff --git a/src/PowerShellEditorServices/Server/PsesServiceCollectionExtensions.cs b/src/PowerShellEditorServices/Server/PsesServiceCollectionExtensions.cs
new file mode 100644
index 000000000..cd66847b0
--- /dev/null
+++ b/src/PowerShellEditorServices/Server/PsesServiceCollectionExtensions.cs
@@ -0,0 +1,84 @@
+//
+// Copyright (c) Microsoft. All rights reserved.
+// Licensed under the MIT license. See LICENSE file in the project root for full license information.
+//
+
+using System;
+using System.Collections.Generic;
+using System.Management.Automation.Host;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Logging;
+using Microsoft.PowerShell.EditorServices.Hosting;
+using Microsoft.PowerShell.EditorServices.Services;
+
+namespace Microsoft.PowerShell.EditorServices.Server
+{
+    internal static class PsesServiceCollectionExtensions
+    {
+        public static IServiceCollection AddPsesLanguageServices (
+            this IServiceCollection collection,
+            ProfilePaths profilePaths,
+            HashSet<string> featureFlags,
+            bool enableConsoleRepl,
+            PSHost internalHost,
+            HostDetails hostDetails,
+            string[] additionalModules)
+        {
+            return collection.AddSingleton<WorkspaceService>()
+                .AddSingleton<SymbolsService>()
+                .AddSingleton<ConfigurationService>()
+                .AddSingleton<PowerShellContextService>(
+                    (provider) =>
+                        PowerShellContextService.Create(
+                            provider.GetService<ILoggerFactory>(),
+                            provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>(),
+                            profilePaths,
+                            featureFlags,
+                            enableConsoleRepl,
+                            internalHost,
+                            hostDetails,
+                            additionalModules))
+                .AddSingleton<TemplateService>()
+                .AddSingleton<EditorOperationsService>()
+                .AddSingleton<RemoteFileManagerService>()
+                .AddSingleton<ExtensionService>(
+                    (provider) =>
+                    {
+                        var extensionService = new ExtensionService(
+                            provider.GetService<PowerShellContextService>(),
+                            provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>());
+                        extensionService.InitializeAsync(
+                            serviceProvider: provider,
+                            editorOperations: provider.GetService<EditorOperationsService>())
+                            .Wait();
+                        return extensionService;
+                    })
+                .AddSingleton<AnalysisService>(
+                    (provider) =>
+                    {
+                        return AnalysisService.Create(
+                            provider.GetService<ConfigurationService>(),
+                            provider.GetService<OmniSharp.Extensions.LanguageServer.Protocol.Server.ILanguageServer>(),
+                            provider.GetService<ILoggerFactory>().CreateLogger<AnalysisService>());
+                    });
+        }
+
+        public static IServiceCollection AddPsesDebugServices(
+            this IServiceCollection collection,
+            IServiceProvider languageServiceProvider,
+            PsesDebugServer psesDebugServer,
+            bool useTempSession)
+        {
+            return collection.AddSingleton(languageServiceProvider.GetService<PowerShellContextService>())
+                .AddSingleton(languageServiceProvider.GetService<WorkspaceService>())
+                .AddSingleton(languageServiceProvider.GetService<RemoteFileManagerService>())
+                .AddSingleton<PsesDebugServer>(psesDebugServer)
+                .AddSingleton<DebugService>()
+                .AddSingleton<DebugStateService>(new DebugStateService
+                {
+                     OwnsEditorSession = useTempSession
+                })
+                .AddSingleton<DebugEventHandlerService>();
+        }
+    }
+}
diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
index addf829a1..747a8a9b2 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
@@ -43,10 +43,17 @@ public ConfigurationDoneHandler(
             _workspaceService = workspaceService;
         }
 
-        public Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request, CancellationToken cancellationToken)
+        public async Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request, CancellationToken cancellationToken)
         {
             _debugService.IsClientAttached = true;
 
+            if (_debugStateService.OwnsEditorSession)
+            {
+                // If this is a debug-only session, we need to start
+                // the command loop manually
+                _powerShellContextService.ConsoleReader.StartCommandLoop();
+            }
+
             if (!string.IsNullOrEmpty(_debugStateService.ScriptToLaunch))
             {
                 if (_powerShellContextService.SessionState == PowerShellContextState.Ready)
@@ -63,14 +70,6 @@ public Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request
 
             if (_debugStateService.IsInteractiveDebugSession)
             {
-                if (_debugStateService.OwnsEditorSession)
-                {
-                    // If this is a debug-only session, we need to start
-                    // the command loop manually
-                    // TODO: Bring this back
-                    //_editorSession.HostInput.StartCommandLoop();
-                }
-
                 if (_debugService.IsDebuggerStopped)
                 {
                     if (_debugService.CurrentDebuggerStoppedEventArgs != null)
@@ -88,7 +87,7 @@ public Task<ConfigurationDoneResponse> Handle(ConfigurationDoneArguments request
                 }
             }
 
-            return Task.FromResult(new ConfigurationDoneResponse());
+            return new ConfigurationDoneResponse();
         }
 
         private async Task LaunchScriptAsync(string scriptToLaunch)
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
index dfe550c18..a1f54a0de 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
@@ -1793,7 +1793,7 @@ private void OnExecutionStatusChanged(
 
         private void PowerShellContext_RunspaceChangedAsync(object sender, RunspaceChangedEventArgs e)
         {
-            _languageServer.SendNotification(
+            _languageServer?.SendNotification(
                 "powerShell/runspaceChanged",
                 new MinifiedRunspaceDetails(e.NewRunspace));
         }
@@ -1831,7 +1831,7 @@ public MinifiedRunspaceDetails(RunspaceDetails eventArgs)
         /// <param name="e">details of the execution status change</param>
         private void PowerShellContext_ExecutionStatusChangedAsync(object sender, ExecutionStatusChangedEventArgs e)
         {
-            _languageServer.SendNotification(
+            _languageServer?.SendNotification(
                 "powerShell/executionStatusChanged",
                 e);
         }