diff --git a/PowerShellEditorServices.Common.props b/PowerShellEditorServices.Common.props
index 2ab30ebc7..cdb72f19d 100644
--- a/PowerShellEditorServices.Common.props
+++ b/PowerShellEditorServices.Common.props
@@ -11,6 +11,5 @@
     <RepositoryType>git</RepositoryType>
     <RepositoryUrl>https://github.com/PowerShell/PowerShellEditorServices</RepositoryUrl>
     <DebugType>portable</DebugType>
-    <DefineConstants Condition=" '$(ExtraDefineConstants)' != '' ">$(DefineConstants);$(ExtraDefineConstants)</DefineConstants>
   </PropertyGroup>
 </Project>
diff --git a/PowerShellEditorServices.build.ps1 b/PowerShellEditorServices.build.ps1
index 8df6c5fc1..fbd126708 100644
--- a/PowerShellEditorServices.build.ps1
+++ b/PowerShellEditorServices.build.ps1
@@ -259,20 +259,20 @@ task TestServer TestServerWinPS,TestServerPS7,TestServerPS72
 
 task TestServerWinPS -If (-not $script:IsNix) {
     Set-Location .\test\PowerShellEditorServices.Test\
-    exec { & $script:dotnetExe test -p:ExtraDefineConstants=TEST --logger trx -f $script:NetRuntime.Desktop (DotNetTestFilter) }
+    exec { & $script:dotnetExe test --logger trx -f $script:NetRuntime.Desktop (DotNetTestFilter) }
 }
 
 task TestServerPS7 -If (-not $script:IsRosetta) {
     Set-Location .\test\PowerShellEditorServices.Test\
     Invoke-WithCreateDefaultHook -NewModulePath $script:PSCoreModulePath {
-        exec { & $script:dotnetExe test -p:ExtraDefineConstants=TEST --logger trx -f $script:NetRuntime.PS7 (DotNetTestFilter) }
+        exec { & $script:dotnetExe test --logger trx -f $script:NetRuntime.PS7 (DotNetTestFilter) }
     }
 }
 
 task TestServerPS72 {
     Set-Location .\test\PowerShellEditorServices.Test\
     Invoke-WithCreateDefaultHook -NewModulePath $script:PSCoreModulePath {
-        exec { & $script:dotnetExe test -p:ExtraDefineConstants=TEST --logger trx -f $script:NetRuntime.PS72 (DotNetTestFilter) }
+        exec { & $script:dotnetExe test --logger trx -f $script:NetRuntime.PS72 (DotNetTestFilter) }
     }
 }
 
@@ -281,13 +281,13 @@ task TestE2E {
 
     $env:PWSH_EXE_NAME = if ($IsCoreCLR) { "pwsh" } else { "powershell" }
     $NetRuntime = if ($IsRosetta) { $script:NetRuntime.PS72 } else { $script:NetRuntime.PS7 }
-    exec { & $script:dotnetExe test -p:ExtraDefineConstants=TEST --logger trx -f $NetRuntime (DotNetTestFilter) }
+    exec { & $script:dotnetExe test --logger trx -f $NetRuntime (DotNetTestFilter) }
 
     # Run E2E tests in ConstrainedLanguage mode.
     if (!$script:IsNix) {
         try {
             [System.Environment]::SetEnvironmentVariable("__PSLockdownPolicy", "0x80000007", [System.EnvironmentVariableTarget]::Machine);
-            exec { & $script:dotnetExe test -p:ExtraDefineConstants=TEST --logger trx -f $script:NetRuntime.PS7 (DotNetTestFilter) }
+            exec { & $script:dotnetExe test --logger trx -f $script:NetRuntime.PS7 (DotNetTestFilter) }
         } finally {
             [System.Environment]::SetEnvironmentVariable("__PSLockdownPolicy", $null, [System.EnvironmentVariableTarget]::Machine);
         }
diff --git a/src/PowerShellEditorServices.Hosting/Internal/EditorServicesRunner.cs b/src/PowerShellEditorServices.Hosting/Internal/EditorServicesRunner.cs
index b4dbf7c63..e49da8527 100644
--- a/src/PowerShellEditorServices.Hosting/Internal/EditorServicesRunner.cs
+++ b/src/PowerShellEditorServices.Hosting/Internal/EditorServicesRunner.cs
@@ -292,7 +292,8 @@ private HostStartupInfo CreateHostStartupInfo()
                 _config.LogPath,
                 (int)_config.LogLevel,
                 consoleReplEnabled: _config.ConsoleRepl != ConsoleReplKind.None,
-                usesLegacyReadLine: _config.ConsoleRepl == ConsoleReplKind.LegacyReadLine);
+                usesLegacyReadLine: _config.ConsoleRepl == ConsoleReplKind.LegacyReadLine,
+                bundledModulePath: _config.BundledModulePath);
         }
 
         private void WriteStartupBanner()
diff --git a/src/PowerShellEditorServices/Hosting/HostStartupInfo.cs b/src/PowerShellEditorServices/Hosting/HostStartupInfo.cs
index 5f3ae7647..7612cd5a0 100644
--- a/src/PowerShellEditorServices/Hosting/HostStartupInfo.cs
+++ b/src/PowerShellEditorServices/Hosting/HostStartupInfo.cs
@@ -106,7 +106,10 @@ public sealed class HostStartupInfo
         /// cref="Serilog.Events.LogEventLevel"/>, hence it is an <c>int</c>.
         /// </remarks>
         public int LogLevel { get; }
-
+        /// <summary>
+        /// The path to find the Bundled Modules        /// 
+        /// </summary>
+        public string BundledModulePath { get; }
         #endregion
 
         #region Constructors
@@ -135,6 +138,7 @@ public sealed class HostStartupInfo
         /// <param name="logLevel">The minimum log event level.</param>
         /// <param name="consoleReplEnabled">Enable console if true.</param>
         /// <param name="usesLegacyReadLine">Use PSReadLine if false, otherwise use the legacy readline implementation.</param>
+        /// <param name="bundledModulePath">The path to the Modules folder, helps with loading the bundled PSReadLine and other included modules</param>
         public HostStartupInfo(
             string name,
             string profileId,
@@ -147,7 +151,9 @@ public HostStartupInfo(
             string logPath,
             int logLevel,
             bool consoleReplEnabled,
-            bool usesLegacyReadLine)
+            bool usesLegacyReadLine,
+            string bundledModulePath
+            )
         {
             Name = name ?? DefaultHostName;
             ProfileId = profileId ?? DefaultHostProfileId;
@@ -161,6 +167,7 @@ public HostStartupInfo(
             LogLevel = logLevel;
             ConsoleReplEnabled = consoleReplEnabled;
             UsesLegacyReadLine = usesLegacyReadLine;
+            BundledModulePath = bundledModulePath;
         }
 
         #endregion
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
index f226dd8d3..b98754951 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
@@ -32,10 +32,18 @@ namespace Microsoft.PowerShell.EditorServices.Services
     /// </summary>
     internal class PowerShellContextService : IHostSupportsInteractiveSession
     {
-        private static readonly string s_commandsModulePath = Path.GetFullPath(
+        private static string s_bundledModulesPath = Path.Combine(Path.GetDirectoryName(Assembly.GetExecutingAssembly().Location), "..", "..");
+
+        private static string s_commandsModulePath => Path.GetFullPath(
+            Path.Combine(
+                s_bundledModulesPath,
+                "PowerShellEditorServices",
+                "Commands",
+                "PowerShellEditorServices.Commands.psd1"));
+        private static string _psReadLineModulePath => Path.GetFullPath(
             Path.Combine(
-                Path.GetDirectoryName(Assembly.GetExecutingAssembly().Location),
-                "../../Commands/PowerShellEditorServices.Commands.psd1"));
+                s_bundledModulesPath,
+                "PSReadLine"));
 
         private static readonly Action<Runspace, ApartmentState> s_runspaceApartmentStateSetter;
         private static readonly PropertyInfo s_writeStreamProperty;
@@ -190,7 +198,10 @@ public static PowerShellContextService Create(
             HostStartupInfo hostStartupInfo)
         {
             Validate.IsNotNull(nameof(hostStartupInfo), hostStartupInfo);
-
+            s_bundledModulesPath = !string.IsNullOrEmpty(hostStartupInfo.BundledModulePath) && Directory.Exists(hostStartupInfo.BundledModulePath) 
+                ? hostStartupInfo.BundledModulePath
+                : s_bundledModulesPath;
+            
             var logger = factory.CreateLogger<PowerShellContextService>();
 
             bool shouldUsePSReadLine = hostStartupInfo.ConsoleReplEnabled
@@ -215,12 +226,18 @@ public static PowerShellContextService Create(
 
             logger.LogTrace("Creating initial PowerShell runspace");
             Runspace initialRunspace = PowerShellContextService.CreateRunspace(psHost, hostStartupInfo.LanguageMode);
-            powerShellContext.Initialize(hostStartupInfo.ProfilePaths, initialRunspace, true, hostUserInterface);
+            powerShellContext.Initialize(hostStartupInfo, initialRunspace, true, hostUserInterface);
             powerShellContext.ImportCommandsModuleAsync();
 
             // TODO: This can be moved to the point after the $psEditor object
             // gets initialized when that is done earlier than LanguageServer.Initialize
-            foreach (string module in hostStartupInfo.AdditionalModules)
+            var modulesToImport = new List<string>();
+            if(hostStartupInfo.ConsoleReplEnabled)
+            {
+                modulesToImport.Add(_psReadLineModulePath);
+            }
+            modulesToImport.AddRange(hostStartupInfo.AdditionalModules);
+            foreach (string module in modulesToImport)
             {
                 var command =
                     new PSCommand()
@@ -305,7 +322,7 @@ public static Runspace CreateRunspace(PSHost psHost, PSLanguageMode languageMode
         /// <param name="ownsInitialRunspace">If true, the PowerShellContext owns this runspace.</param>
         /// <param name="consoleHost">An IHostOutput implementation.  Optional.</param>
         public void Initialize(
-            ProfilePathInfo profilePaths,
+            HostStartupInfo hostStartupInfo,
             Runspace initialRunspace,
             bool ownsInitialRunspace,
             IHostOutput consoleHost)
@@ -359,7 +376,7 @@ public void Initialize(
             this.ConfigureRunspaceCapabilities(this.CurrentRunspace);
 
             // Set the $profile variable in the runspace
-            this.profilePaths = profilePaths;
+            this.profilePaths = hostStartupInfo.ProfilePaths;
             if (profilePaths != null)
             {
                 this.SetProfileVariableInCurrentRunspace(profilePaths);
@@ -394,9 +411,14 @@ public void Initialize(
                 this.versionSpecificOperations);
             this.InvocationEventQueue = InvocationEventQueue.Create(this, this.PromptNest);
 
+            if (VersionUtils.IsWindows)
+            {
+                this.SetExecutionPolicy();
+            }
+
             if (powerShellVersion.Major >= 5 &&
                 this.isPSReadLineEnabled &&
-                PSReadLinePromptContext.TryGetPSReadLineProxy(logger, initialRunspace, out PSReadLineProxy proxy))
+                PSReadLinePromptContext.TryGetPSReadLineProxy(logger, initialRunspace, hostStartupInfo.BundledModulePath, out PSReadLineProxy proxy))
             {
                 this.PromptContext = new PSReadLinePromptContext(
                     this,
@@ -409,10 +431,6 @@ public void Initialize(
                 this.PromptContext = new LegacyReadLineContext(this);
             }
 
-            if (VersionUtils.IsWindows)
-            {
-                this.SetExecutionPolicy();
-            }
         }
 
         /// <summary>
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs b/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
index 5f4931854..3633ad1d3 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
@@ -17,20 +17,6 @@ namespace Microsoft.PowerShell.EditorServices.Services.PowerShellContext
 
     internal class PSReadLinePromptContext : IPromptContext
     {
-        private static readonly string _psReadLineModulePath = Path.Combine(
-            Path.GetDirectoryName(typeof(PSReadLinePromptContext).Assembly.Location),
-            "..",
-            "..",
-            "..",
-#if TEST
-            // When using xUnit (dotnet test) the assemblies are deployed to the
-            // test project folder, invalidating our relative path assumption.
-            "..",
-            "..",
-            "module",
-#endif
-            "PSReadLine");
-
         private static readonly Lazy<CmdletInfo> s_lazyInvokeReadLineForEditorServicesCmdletInfo = new Lazy<CmdletInfo>(() =>
         {
             var type = Type.GetType("Microsoft.PowerShell.EditorServices.Commands.InvokeReadLineForEditorServicesCommand, Microsoft.PowerShell.EditorServices.Hosting");
@@ -79,9 +65,11 @@ internal PSReadLinePromptContext(
         internal static bool TryGetPSReadLineProxy(
             ILogger logger,
             Runspace runspace,
+            string bundledModulePath,
             out PSReadLineProxy readLineProxy)
         {
             readLineProxy = null;
+            string _psReadLineModulePath = Path.Combine(bundledModulePath, "PSReadLine");
             logger.LogTrace("Attempting to load PSReadLine");
             using (var pwsh = PowerShell.Create())
             {
@@ -94,10 +82,24 @@ internal static bool TryGetPSReadLineProxy(
 
                 if (psReadLineType == null)
                 {
-                    logger.LogWarning("PSConsoleReadline type not found: {Reason}", pwsh.HadErrors ? pwsh.Streams.Error[0].ToString() : "<Unknown reason>");
-                    return false;
+                    logger.LogWarning("PSConsoleReadline type not found using Type.GetType(): {Reason}", pwsh.HadErrors ? pwsh.Streams.Error[0].ToString() : "<Unknown reason>");
+                    logger.LogWarning("Searching loaded assemblies...");
+                    var allAssemblies = AppDomain.CurrentDomain.GetAssemblies();
+                    var assemblies = allAssemblies.FirstOrDefault(a => a.FullName.Contains("Microsoft.PowerShell.PSReadLine2"));
+                    var type = assemblies?.ExportedTypes?.FirstOrDefault(a => a.FullName == "Microsoft.PowerShell.PSConsoleReadLine");
+                    if(type is not null)
+                    {
+                        logger.LogInformation("Found PSConsoleReadLine in loaded assemblies.");                    
+                        psReadLineType = type;
+                    }
+                    else
+                    {
+                        logger.LogError("Unable to find PSConsoleReadLine in loaded assembles.");
+                        return false;
+                    }
                 }
 
+
                 try
                 {
                     readLineProxy = new PSReadLineProxy(psReadLineType, logger);
@@ -108,6 +110,7 @@ internal static bool TryGetPSReadLineProxy(
                     // Could be an older version, a custom build, or something a newer version with
                     // breaking changes.
                     logger.LogWarning("PSReadLineProxy unable to be initialized: {Reason}", e);
+                    System.Console.WriteLine("PSReadLineProxy unable to be initialized");
                     return false;
                 }
             }
diff --git a/test/PowerShellEditorServices.Test/PowerShellContextFactory.cs b/test/PowerShellEditorServices.Test/PowerShellContextFactory.cs
index 4eb93395a..5fd8ecbd1 100644
--- a/test/PowerShellEditorServices.Test/PowerShellContextFactory.cs
+++ b/test/PowerShellEditorServices.Test/PowerShellContextFactory.cs
@@ -31,6 +31,9 @@ internal static class PowerShellContextFactory
                         TestUtilities.NormalizePath("../../../../PowerShellEditorServices.Test.Shared/Test.PowerShellEditorServices_profile.ps1")),
                     Path.GetFullPath(
                         TestUtilities.NormalizePath("../../../../PowerShellEditorServices.Test.Shared/ProfileTest.ps1")));
+        public static readonly string BundledModulesPath = 
+            Path.GetFullPath(
+                        TestUtilities.NormalizePath("../../../../../module"));
 
         public static System.Management.Automation.Runspaces.Runspace initialRunspace;
 
@@ -50,7 +53,8 @@ public static PowerShellContextService Create(ILogger logger)
                 null,
                 0,
                 consoleReplEnabled: false,
-                usesLegacyReadLine: false);
+                usesLegacyReadLine: false,
+                bundledModulePath: BundledModulesPath);
 
             initialRunspace = PowerShellContextService.CreateRunspace(
                     testHostDetails,
@@ -59,7 +63,7 @@ public static PowerShellContextService Create(ILogger logger)
                     logger);
 
             powerShellContext.Initialize(
-                TestProfilePaths,
+                testHostDetails,
                 initialRunspace,
                 ownsInitialRunspace: true,
                 consoleHost: null);
diff --git a/test/PowerShellEditorServices.Test/Session/PowerShellContextTests.cs b/test/PowerShellEditorServices.Test/Session/PowerShellContextTests.cs
index 4cf1fef8c..16043aaac 100644
--- a/test/PowerShellEditorServices.Test/Session/PowerShellContextTests.cs
+++ b/test/PowerShellEditorServices.Test/Session/PowerShellContextTests.cs
@@ -6,6 +6,7 @@
 using System.IO;
 using System.Linq;
 using System.Management.Automation;
+using System.Reflection;
 using System.Runtime.InteropServices;
 using System.Threading.Tasks;
 using Microsoft.Extensions.Logging.Abstractions;
@@ -151,11 +152,20 @@ await this.powerShellContext.ExecuteCommandAsync<string>(
         [SkippableFact]
         public async Task CanGetPSReadLineProxy()
         {
-            Skip.If(IsWindows, "This test doesn't work on Windows for some reason.");
+            var directory = Path.Combine(AppDomain.CurrentDomain.BaseDirectory, AppDomain.CurrentDomain.RelativeSearchPath ?? "");
+            string s_bundledModulesPath = Path.GetFullPath(Path.Combine(directory,
+            "..",
+            "..",
+            "..",
+            "..",
+            "..",
+            "module"
+            ));
             Assert.True(PSReadLinePromptContext.TryGetPSReadLineProxy(
-                NullLogger.Instance,
-                PowerShellContextFactory.initialRunspace,
-                out PSReadLineProxy proxy));
+                    NullLogger.Instance,
+                    PowerShellContextFactory.initialRunspace,
+                    s_bundledModulesPath,
+                    out PSReadLineProxy proxy));
         }
 
         #region Helper Methods