diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs b/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
index 99ea3b40a..6028baecd 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/Session/PSReadLinePromptContext.cs
@@ -12,6 +12,7 @@
 
 namespace Microsoft.PowerShell.EditorServices.Services.PowerShellContext
 {
+    using System.Collections.Generic;
     using System.Management.Automation;
     using Microsoft.Extensions.Logging;
 
@@ -44,6 +45,15 @@ internal class PSReadLinePromptContext : IPromptContext
                 return [Microsoft.PowerShell.PSConsoleReadLine, Microsoft.PowerShell.PSReadLine2, Version=2.0.0.0, Culture=neutral, PublicKeyToken=null]
             }";
 
+        private static ExecutionOptions s_psrlExecutionOptions = new ExecutionOptions
+        {
+            WriteErrorsToHost = false,
+            WriteOutputToHost = false,
+            InterruptCommandPrompt = false,
+            AddToHistory = false,
+            IsReadLine = true,
+        };
+
         private readonly PowerShellContextService _powerShellContext;
 
         private readonly PromptNest _promptNest;
@@ -68,7 +78,6 @@ internal PSReadLinePromptContext(
             _consoleReadLine = new ConsoleReadLine(powerShellContext);
             _readLineProxy = readLineProxy;
 
-
             _readLineProxy.OverrideReadKey(
                 intercept => ConsoleProxy.SafeReadKey(
                     intercept,
@@ -81,6 +90,7 @@ internal static bool TryGetPSReadLineProxy(
             out PSReadLineProxy readLineProxy)
         {
             readLineProxy = null;
+            logger.LogTrace("Attempting to load PSReadLine");
             using (var pwsh = PowerShell.Create())
             {
                 pwsh.Runspace = runspace;
@@ -91,6 +101,7 @@ internal static bool TryGetPSReadLineProxy(
 
                 if (psReadLineType == null)
                 {
+                    logger.LogWarning("PSReadLine unable to be loaded: {Reason}", pwsh.HadErrors ? pwsh.Streams.Error[0].ToString() : "<Unknown reason>");
                     return false;
                 }
 
@@ -98,11 +109,12 @@ internal static bool TryGetPSReadLineProxy(
                 {
                     readLineProxy = new PSReadLineProxy(psReadLineType, logger);
                 }
-                catch (InvalidOperationException)
+                catch (InvalidOperationException e)
                 {
                     // The Type we got back from PowerShell doesn't have the members we expected.
                     // Could be an older version, a custom build, or something a newer version with
                     // breaking changes.
+                    logger.LogWarning("PSReadLine unable to be loaded: {Reason}", e);
                     return false;
                 }
             }
@@ -119,38 +131,27 @@ public async Task<string> InvokeReadLineAsync(bool isCommandLine, CancellationTo
                 throw new TaskCanceledException();
             }
 
-            try
+            if (!isCommandLine)
             {
-                if (!isCommandLine)
-                {
-                    return await _consoleReadLine.InvokeLegacyReadLineAsync(
-                        isCommandLine: false,
-                        _readLineCancellationSource.Token).ConfigureAwait(false);
-                }
+                return await _consoleReadLine.InvokeLegacyReadLineAsync(
+                    isCommandLine: false,
+                    _readLineCancellationSource.Token).ConfigureAwait(false);
+            }
 
-                var result = (await _powerShellContext.ExecuteCommandAsync<string>(
-                    new PSCommand()
-                        .AddScript(ReadLineScript)
-                        .AddArgument(_readLineCancellationSource.Token),
-                    errorMessages: null,
-                    new ExecutionOptions()
-                    {
-                        WriteErrorsToHost = false,
-                        WriteOutputToHost = false,
-                        InterruptCommandPrompt = false,
-                        AddToHistory = false,
-                        IsReadLine = isCommandLine
-                    }).ConfigureAwait(false))
-                    .FirstOrDefault();
+            var readLineCommand = new PSCommand()
+                .AddScript(ReadLineScript)
+                .AddArgument(_readLineCancellationSource.Token);
 
-                return cancellationToken.IsCancellationRequested
-                    ? string.Empty
-                    : result;
-            }
-            finally
-            {
-                _readLineCancellationSource = null;
-            }
+            IEnumerable<string> readLineResults = await _powerShellContext.ExecuteCommandAsync<string>(
+                readLineCommand,
+                errorMessages: null,
+                s_psrlExecutionOptions).ConfigureAwait(false);
+
+            string line = readLineResults.FirstOrDefault();
+
+            return cancellationToken.IsCancellationRequested
+                ? string.Empty
+                : line;
         }
 
         public void AbortReadLine()