diff --git a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
index 7750585c0..1ded392ff 100644
--- a/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
+++ b/src/PowerShellEditorServices/Services/DebugAdapter/Handlers/ConfigurationDoneHandler.cs
@@ -163,16 +163,9 @@ private static PSCommand BuildPSCommandFromArguments(string command, IReadOnlyLi
 
             foreach (string arg in arguments)
             {
-                sb.Append(' ');
-
-                if (StringEscaping.PowerShellArgumentNeedsEscaping(arg))
-                {
-                    sb.Append(StringEscaping.SingleQuoteAndEscape(arg));
-                }
-                else
-                {
-                    sb.Append(arg);
-                }
+                sb
+                .Append(' ')
+                .Append(StringEscaping.EscapePowershellArgument(arg));
             }
 
             return new PSCommand().AddScript(sb.ToString());
diff --git a/src/PowerShellEditorServices/Utility/StringEscaping.cs b/src/PowerShellEditorServices/Utility/StringEscaping.cs
index 5736a9aad..2113d20d4 100644
--- a/src/PowerShellEditorServices/Utility/StringEscaping.cs
+++ b/src/PowerShellEditorServices/Utility/StringEscaping.cs
@@ -8,14 +8,24 @@ internal static class StringEscaping
     {
         public static StringBuilder SingleQuoteAndEscape(string s)
         {
+            var dequotedString = s.TrimStart('\'').TrimEnd('\'');
+            var psEscapedInnerQuotes = dequotedString.Replace("'", "`'");
             return new StringBuilder(s.Length)
-                .Append("'")
-                .Append(s.Replace("'", "''"))
-                .Append("'");
+                .Append('\'')
+                .Append(psEscapedInnerQuotes)
+                .Append('\'');
         }
 
         public static bool PowerShellArgumentNeedsEscaping(string argument)
         {
+            //Already quoted arguments dont require escaping unless there is a quote inside as well
+            if (argument.StartsWith("'") && argument.EndsWith("'"))
+            {
+                var dequotedString = argument.TrimStart('\'').TrimEnd('\'');
+                // need to escape if there is a single quote between single quotes
+                return dequotedString.Contains("'");
+            }
+
             foreach (char c in argument)
             {
                 switch (c)
@@ -33,5 +43,18 @@ public static bool PowerShellArgumentNeedsEscaping(string argument)
 
             return false;
         }
+
+        public static string EscapePowershellArgument(string argument)
+        {
+            if (PowerShellArgumentNeedsEscaping(argument))
+            {
+                return SingleQuoteAndEscape(argument).ToString();
+            }
+            else
+            {
+                return argument;
+            }
+        }
+
     }
 }
diff --git a/test/PowerShellEditorServices.Test/Session/PathEscapingTests.cs b/test/PowerShellEditorServices.Test/Session/PathEscapingTests.cs
index 495166e09..34c8a4951 100644
--- a/test/PowerShellEditorServices.Test/Session/PathEscapingTests.cs
+++ b/test/PowerShellEditorServices.Test/Session/PathEscapingTests.cs
@@ -65,11 +65,13 @@ public void CorrectlyWildcardEscapesPaths_Spaces(string unescapedPath, string es
         [InlineData("C:\\look\\an*\\here.ps1", "'C:\\look\\an*\\here.ps1'")]
         [InlineData("/Users/me/Documents/?here.ps1", "'/Users/me/Documents/?here.ps1'")]
         [InlineData("/Brackets [and s]paces/path.ps1", "'/Brackets [and s]paces/path.ps1'")]
-        [InlineData("/file path/that isn't/normal/", "'/file path/that isn''t/normal/'")]
+        [InlineData("/file path/that isn't/normal/", "'/file path/that isn`'t/normal/'")]
         [InlineData("/CJK.chars/脚本/hello.ps1", "'/CJK.chars/脚本/hello.ps1'")]
         [InlineData("/CJK chars/脚本/[hello].ps1", "'/CJK chars/脚本/[hello].ps1'")]
         [InlineData("C:\\Animal s\\утка\\quack.ps1", "'C:\\Animal s\\утка\\quack.ps1'")]
         [InlineData("C:\\&nimals\\утка\\qu*ck?.ps1", "'C:\\&nimals\\утка\\qu*ck?.ps1'")]
+        [InlineData("../../Quote'InPathTest.ps1", "'../../Quote`'InPathTest.ps1'")]
+
         public void CorrectlyQuoteEscapesPaths(string unquotedPath, string expectedQuotedPath)
         {
             string extensionQuotedPath = StringEscaping.SingleQuoteAndEscape(unquotedPath).ToString();
diff --git a/test/PowerShellEditorServices.Test/Utility/ArgumentEscapingTests.cs b/test/PowerShellEditorServices.Test/Utility/ArgumentEscapingTests.cs
new file mode 100644
index 000000000..002d3819f
--- /dev/null
+++ b/test/PowerShellEditorServices.Test/Utility/ArgumentEscapingTests.cs
@@ -0,0 +1,54 @@
+using Xunit;
+using Microsoft.PowerShell.EditorServices.Utility;
+using System.Management.Automation;
+using System.Linq;
+
+namespace Microsoft.PowerShell.EditorServices.Test.Session
+{
+    public class ArgumentEscapingTests
+    {
+        [Trait("Category", "ArgumentEscaping")]
+        [Theory]
+        [InlineData("/path/to/file", "/path/to/file")]
+        [InlineData("'/path/to/file'", "'/path/to/file'")]
+        [InlineData("not|allowed|pipeline", "'not|allowed|pipeline'")]
+        [InlineData("doublequote\"inmiddle", "'doublequote\"inmiddle'")]
+        [InlineData("am&persand", "'am&persand'")]
+        [InlineData("semicolon;", "'semicolon;'")]
+        [InlineData(":colon", "':colon'")]
+        [InlineData(" has space s", "' has space s'")]
+        [InlineData("[brackets]areOK", "[brackets]areOK")]
+        [InlineData("$(expressionsAreOK)", "$(expressionsAreOK)")]
+        [InlineData("{scriptBlocksAreOK}", "{scriptBlocksAreOK}")]
+        [InlineData("'quote ' in middle of argument'", "'quote `' in middle of argument'")]
+
+        public void CorrectlyEscapesPowerShellArguments(string Arg, string expectedArg)
+        {
+            string quotedArg = StringEscaping.EscapePowershellArgument(Arg);
+            Assert.Equal(expectedArg, quotedArg);
+        }
+
+        [Trait("Category", "ArgumentEscaping")]
+        [Theory]
+        [InlineData("/path/to/file", "/path/to/file")]
+        [InlineData("'/path/to/file'", "/path/to/file")]
+        [InlineData("not|allowed|pipeline", "not|allowed|pipeline")]
+        [InlineData("doublequote\"inmiddle", "doublequote\"inmiddle")]
+        [InlineData("am&persand", "am&persand")]
+        [InlineData("semicolon;", "semicolon;")]
+        [InlineData(":colon", ":colon")]
+        [InlineData(" has space s", " has space s")]
+        [InlineData("[brackets]areOK", "[brackets]areOK")]
+        [InlineData("$(echo 'expressionsAreOK')", "expressionsAreOK")]
+        // [InlineData("{scriptBlocksAreOK}", "{scriptBlocksAreOK}")]
+        public void CanEvaluateArgumentsSafely(string Arg, string expectedOutput)
+        {
+            var escapedArg = StringEscaping.EscapePowershellArgument(Arg);
+            var psCommand = new PSCommand().AddScript($"& Write-Output {escapedArg}");
+            using var pwsh = System.Management.Automation.PowerShell.Create();
+            pwsh.Commands = psCommand;
+            var scriptOutput = pwsh.Invoke<string>().First();
+            Assert.Equal(expectedOutput, scriptOutput);
+        }
+    }
+}