diff --git a/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs b/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
index 8a010379110..e25586fa55d 100644
--- a/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
+++ b/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
@@ -5043,14 +5043,24 @@ private static void EscapeCharIfNeeded(
                     break;
 
                 default:
-                    // Handle all the different quote types
-                    if (useSingleQuoteEscapeRules && path[index].IsSingleQuote())
+                    if (useSingleQuoteEscapeRules)
                     {
-                        _ = sb.Append('\'');
-                        quotesAreNeeded = true;
+                        // Bareword or singlequoted input string.
+                        if (path[index].IsSingleQuote())
+                        {
+                            // SingleQuotes are escaped with more single quotes. quotesAreNeeded is set so bareword strings can quoted.
+                            _ = sb.Append('\'');
+                            quotesAreNeeded = true;
+                        }
+                        else if (!quotesAreNeeded && stringType == StringConstantType.BareWord && path[index].IsDoubleQuote())
+                        {
+                            // Bareword string with double quote inside. Make sure to quote it so we don't need to escape it.
+                            quotesAreNeeded = true;
+                        }
                     }
-                    else if (!useSingleQuoteEscapeRules && path[index].IsDoubleQuote())
+                    else if (path[index].IsDoubleQuote())
                     {
+                        // Double quoted or bareword with variables input string. Need to escape double quotes.
                         _ = sb.Append('`');
                         quotesAreNeeded = true;
                     }
diff --git a/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1 b/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
index e088d368011..93bdfe89882 100644
--- a/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
+++ b/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
@@ -2257,6 +2257,42 @@ param ($Param1)
 
             Remove-Item -LiteralPath $LiteralPath
         }
+
+        It "Should add single quotes if there are double quotes in bare word file path" {
+			$BadQuote = [char]8220
+		    $TestFile1 = Join-Path -Path $TestDrive -ChildPath "Test1${BadQuote}File"
+            $null = New-Item -Path $TestFile1 -Force
+            $res = TabExpansion2 -inputScript "Get-ChildItem -Path $TestDrive\"
+            ($res.CompletionMatches | Where-Object ListItemText -Like "Test1?File").CompletionText | Should -Be "'$TestFile1'"
+            Remove-Item -LiteralPath $TestFile1 -Force
+        }
+
+        It "Should escape double quote if the input string uses double quotes" {
+			$BadQuote = [char]8220
+		    $TestFile1 = Join-Path -Path $TestDrive -ChildPath "Test1${BadQuote}File"
+            $null = New-Item -Path $TestFile1 -Force
+            $res = TabExpansion2 -inputScript "Get-ChildItem -Path `"$TestDrive\"
+            $Expected = "`"$($TestFile1.Insert($TestFile1.LastIndexOf($BadQuote), '`'))`""
+            ($res.CompletionMatches | Where-Object ListItemText -Like "Test1?File").CompletionText | Should -Be $Expected
+            Remove-Item -LiteralPath $TestFile1 -Force
+        }
+
+        It "Should escape single quotes in file paths" {
+			$SingleQuote = "'"
+		    $TestFile1 = Join-Path -Path $TestDrive -ChildPath "Test1${SingleQuote}File"
+            $null = New-Item -Path $TestFile1 -Force
+            # Regardless if the input string was singlequoted or not, we expect to add surrounding single quotes and
+            # escape the single quote in the file path with another singlequote.
+            $Expected = "'$($TestFile1.Insert($TestFile1.LastIndexOf($SingleQuote), "'"))'"
+
+            $res = TabExpansion2 -inputScript "Get-ChildItem -Path '$TestDrive\"
+            ($res.CompletionMatches | Where-Object ListItemText -Like "Test1?File").CompletionText | Should -Be $Expected
+
+            $res = TabExpansion2 -inputScript "Get-ChildItem -Path $TestDrive\"
+            ($res.CompletionMatches | Where-Object ListItemText -Like "Test1?File").CompletionText | Should -Be $Expected
+
+            Remove-Item -LiteralPath $TestFile1 -Force
+        }
     }
 
     It 'Should correct slashes in UNC path completion' -Skip:(!$IsWindows) {