diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
index 30eff8760..6780b019a 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/PowerShellContextService.cs
@@ -199,7 +199,7 @@ public static PowerShellContextService Create(
 
             EditorServicesPSHostUserInterface hostUserInterface =
                 hostStartupInfo.ConsoleReplEnabled
-                    ? (EditorServicesPSHostUserInterface)new TerminalPSHostUserInterface(powerShellContext, logger, hostStartupInfo.PSHost)
+                    ? (EditorServicesPSHostUserInterface) new TerminalPSHostUserInterface(powerShellContext, hostStartupInfo.PSHost, shouldUsePSReadLine, logger)
                     : new ProtocolPSHostUserInterface(languageServer, powerShellContext, logger);
 
             EditorServicesPSHost psHost =
@@ -680,7 +680,9 @@ public async Task<IEnumerable<TResult>> ExecuteCommandAsync<TResult>(
                     runspaceHandle = await this.GetRunspaceHandleAsync(executionOptions.IsReadLine).ConfigureAwait(false);
                     if (executionOptions.WriteInputToHost)
                     {
-                        this.WriteOutput(psCommand.Commands[0].CommandText, true);
+                        this.WriteOutput(
+                            psCommand.Commands[0].CommandText,
+                            includeNewLine: true);
                     }
 
                     if (executionTarget == ExecutionTarget.Debugger)
@@ -1074,18 +1076,17 @@ public async Task ExecuteScriptWithArgsAsync(string script, string arguments = n
                 command.AddCommand(script, false);
             }
 
-            if (writeInputToHost)
-            {
-                this.WriteOutput(
-                    script + Environment.NewLine,
-                    true);
-            }
 
             await this.ExecuteCommandAsync<object>(
-                command,
-                errorMessages: null,
-                sendOutputToHost: true,
-                addToHistory: true).ConfigureAwait(false);
+                    command,
+                    errorMessages: null,
+                    new ExecutionOptions
+                    {
+                        WriteInputToHost = true,
+                        WriteOutputToHost = true,
+                        WriteErrorsToHost = true,
+                        AddToHistory = true,
+                    }).ConfigureAwait(false);
         }
 
         /// <summary>
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/EditorServicesPSHostUserInterface.cs b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/EditorServicesPSHostUserInterface.cs
index adb20b7ef..7cd740931 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/EditorServicesPSHostUserInterface.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/EditorServicesPSHostUserInterface.cs
@@ -34,6 +34,8 @@ public abstract class EditorServicesPSHostUserInterface :
 
         private readonly ConcurrentDictionary<ProgressKey, object> currentProgressMessages =
             new ConcurrentDictionary<ProgressKey, object>();
+
+        private readonly bool _isPSReadLineEnabled;
         private PromptHandler activePromptHandler;
         private PSHostRawUserInterface rawUserInterface;
         private CancellationTokenSource commandLoopCancellationToken;
@@ -104,11 +106,13 @@ public abstract class EditorServicesPSHostUserInterface :
         public EditorServicesPSHostUserInterface(
             PowerShellContextService powerShellContext,
             PSHostRawUserInterface rawUserInterface,
+            bool isPSReadLineEnabled,
             ILogger logger)
         {
             this.Logger = logger;
             this.powerShellContext = powerShellContext;
             this.rawUserInterface = rawUserInterface;
+            _isPSReadLineEnabled = isPSReadLineEnabled;
 
             this.powerShellContext.DebuggerStop += PowerShellContext_DebuggerStop;
             this.powerShellContext.DebuggerResumed += PowerShellContext_DebuggerResumed;
@@ -850,7 +854,12 @@ private async Task StartReplLoopAsync(CancellationToken cancellationToken)
                 }
                 finally
                 {
-                    if (!cancellationToken.IsCancellationRequested &&
+                    // This supplies the newline in the Legacy ReadLine when executing code in the terminal via hitting the ENTER key.
+                    // Without this, hitting ENTER with a no input looks like it does nothing (no new prompt is written)
+                    // and also the output would show up on the same line as the code you wanted to execute (the prompt line).
+                    // Since PSReadLine handles ENTER internally to itself, we only want to do this when using the Legacy ReadLine.
+                    if (!_isPSReadLineEnabled &&
+                        !cancellationToken.IsCancellationRequested &&
                         originalCursorTop == await ConsoleProxy.GetCursorTopAsync(cancellationToken).ConfigureAwait(false))
                     {
                         this.WriteLine();
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/ProtocolPSHostUserInterface.cs b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/ProtocolPSHostUserInterface.cs
index 6053245c2..32415922e 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/ProtocolPSHostUserInterface.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/ProtocolPSHostUserInterface.cs
@@ -30,7 +30,11 @@ public ProtocolPSHostUserInterface(
             ILanguageServer languageServer,
             PowerShellContextService powerShellContext,
             ILogger logger)
-            : base(powerShellContext, new SimplePSHostRawUserInterface(logger), logger)
+            : base (
+                powerShellContext,
+                new SimplePSHostRawUserInterface(logger),
+                isPSReadLineEnabled: false,
+                logger)
         {
             _languageServer = languageServer;
         }
diff --git a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/TerminalPSHostUserInterface.cs b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/TerminalPSHostUserInterface.cs
index 93e8173ad..ce6edee46 100644
--- a/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/TerminalPSHostUserInterface.cs
+++ b/src/PowerShellEditorServices/Services/PowerShellContext/Session/Host/TerminalPSHostUserInterface.cs
@@ -37,11 +37,13 @@ public class TerminalPSHostUserInterface : EditorServicesPSHostUserInterface
         /// <param name="internalHost">The InternalHost instance from the origin runspace.</param>
         public TerminalPSHostUserInterface(
             PowerShellContextService powerShellContext,
-            ILogger logger,
-            PSHost internalHost)
-            : base(
+            PSHost internalHost,
+            bool isPSReadLineEnabled,
+            ILogger logger)
+            : base (
                 powerShellContext,
                 new TerminalPSHostRawUserInterface(logger, internalHost),
+                isPSReadLineEnabled,
                 logger)
         {
             this.internalHostUI = internalHost.UI;