diff --git a/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs b/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
index 39a9860df95..cfffd1a1d6a 100644
--- a/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
+++ b/src/System.Management.Automation/engine/CommandCompletion/CompletionCompleters.cs
@@ -4061,10 +4061,8 @@ internal static IEnumerable<CompletionResult> CompleteFilename(CompletionContext
                 var relativePaths = context.GetOption("RelativePaths", @default: defaultRelative);
                 var useLiteralPath = context.GetOption("LiteralPaths", @default: false);
 
-                if (useLiteralPath && LocationGlobber.StringContainsGlobCharacters(wordToComplete))
-                {
-                    wordToComplete = WildcardPattern.Escape(wordToComplete, Utils.Separators.StarOrQuestion);
-                }
+                // We should always escape '[' and ']' if present.
+                wordToComplete = WildcardPattern.Escape(wordToComplete, Utils.Separators.StarOrQuestion);
 
                 if (!defaultRelative && wordToComplete.Length >= 2 && wordToComplete[1] == ':' && char.IsLetter(wordToComplete[0]) && executionContext != null)
                 {
@@ -4073,6 +4071,43 @@ internal static IEnumerable<CompletionResult> CompleteFilename(CompletionContext
                     executionContext.SessionState.Drive.GetAtScope(wordToComplete.Substring(0, 1), "global");
                 }
 
+#if UNIX
+                // We use globbing to get completions.
+                // Globbing is based on system functions which is case-sensitive on Unix.
+                // To make globbing on Unix case-insensitive we transform every char from the input string:
+                // "alias:dir" -> "alias:[dD][iI][rR]"
+                if (context.GetOption("UnixCaseInsensitiveGlobbing", @default: true) == true)
+                {
+                    StringBuilder sb = new StringBuilder(wordToComplete.Length * 4);
+
+                    //wordToComplete = WildcardPattern.Escape(wordToComplete, Utils.Separators.Brackets);
+
+                    // Copy a provider name "as is" without transformation.
+                    var providerPrefixIndex = wordToComplete.IndexOf(':') + 1;
+                    int i;
+                    for (i=0; i < providerPrefixIndex; i++)
+                    {
+                        sb.Append(wordToComplete[i]);
+                    }
+
+                    // Transform rest of input string after a provider prefix.
+                    for (var j=i; j < wordToComplete.Length; j++)
+                    {
+                        var lch = Char.ToLower(wordToComplete[j]);
+                        var uch = Char.ToUpper(wordToComplete[j]);
+                        if (lch != uch)
+                        {
+                            sb.Append('[').Append(lch).Append(uch).Append(']');
+                        }
+                        else
+                        {
+                            sb.Append(wordToComplete[j]);
+                        }
+                    }
+
+                    wordToComplete = sb.ToString();
+                }
+#endif
                 var powerShellExecutionHelper = context.Helper;
                 powerShellExecutionHelper
                     .AddCommandWithPreferenceSetting("Microsoft.PowerShell.Management\\Resolve-Path")
@@ -4215,7 +4250,7 @@ internal static IEnumerable<CompletionResult> CompleteFilename(CompletionContext
                     }
 
                     // Sorting the results by the path
-                    var sortedPsobjs = psobjs.OrderBy(a => a, new ItemPathComparer());
+                    var sortedPsobjs = psobjs.OrderBy(a => a, new ItemPathComparer(wordToComplete));
 
                     foreach (PSObject psobj in sortedPsobjs)
                     {
@@ -6637,6 +6672,13 @@ internal static bool IsAmpersandNeeded(CompletionContext context, bool defaultCh
 
         private class ItemPathComparer : IComparer<PSObject>
         {
+            private String _baseWord;
+
+            public ItemPathComparer(String baseWord)
+            {
+                _baseWord = baseWord + ".*";
+            }
+
             public int Compare(PSObject x, PSObject y)
             {
                 var xPathInfo = PSObject.Base(x) as PathInfo;
@@ -6666,7 +6708,21 @@ public int Compare(PSObject x, PSObject y)
                 if (string.IsNullOrEmpty(xPath) || string.IsNullOrEmpty(yPath))
                     Diagnostics.Assert(false, "Base object of item PSObject should be either PathInfo or FileSystemInfo");
 
-                return String.Compare(xPath, yPath, StringComparison.CurrentCultureIgnoreCase);
+                var result = String.Compare(xPath, yPath, StringComparison.CurrentCultureIgnoreCase);
+#if UNIX
+                if (result == 0)
+                {
+                    if (Regex.IsMatch(xPath, _baseWord))
+                    {
+                        return -1;
+                    }
+                    else
+                    {
+                        return 1;
+                    }
+                }
+#endif
+                return result;
             }
         }
 
diff --git a/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1 b/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
index b199918dd7b..f9ec57bb656 100644
--- a/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
+++ b/test/powershell/Host/TabCompletion/TabCompletion.Tests.ps1
@@ -197,8 +197,12 @@ Describe "TabCompletion" -Tags CI {
 
     Context "File name completion" {
         BeforeAll {
+            $oneSubDirLowerTest = "onesubd"
+            $oneSubDirUpperTest = "oneSubD"
+            $oneSubDirTest = "onesubdir"
+
             $tempDir = Join-Path -Path $TestDrive -ChildPath "baseDir"
-            $oneSubDir = Join-Path -Path $tempDir -ChildPath "oneSubDir"
+            $oneSubDir = Join-Path -Path $tempDir -ChildPath $oneSubDirTest
             $oneSubDirPrime = Join-Path -Path $tempDir -ChildPath "prime"
             $twoSubDir = Join-Path -Path $oneSubDir -ChildPath "twoSubDir"
 
@@ -207,6 +211,13 @@ Describe "TabCompletion" -Tags CI {
             New-Item -Path $oneSubDirPrime -ItemType Directory -Force > $null
             New-Item -Path $twoSubDir -ItemType Directory -Force > $null
 
+            if (!$IsWindows) {
+                $oneSubDirTest2 = "oneSubDir"
+                $oneSubDir2 = Join-Path -Path $tempDir -ChildPath $oneSubDirTest2
+                New-Item -Path $oneSubDir2 -ItemType Directory -Force > $null
+            }
+
+
             $testCases = @(
                 @{ inputStr = "ab"; name = "abc"; localExpected = ".${separator}abc"; oneSubExpected = "..${separator}abc"; twoSubExpected = "..${separator}..${separator}abc" }
                 @{ inputStr = "asaasas"; name = "asaasas!popee"; localExpected = ".${separator}asaasas!popee"; oneSubExpected = "..${separator}asaasas!popee"; twoSubExpected = "..${separator}..${separator}asaasas!popee" }
@@ -241,6 +252,28 @@ Describe "TabCompletion" -Tags CI {
             Pop-Location
         }
 
+        It "TabCompletion should be case-insensitive for file names on Windows" -Skip:(!$IsWindows) {
+            Push-Location -Path $tempDir
+            $res = TabExpansion2 -inputScript $oneSubDirLowerTest -cursorColumn $oneSubDirLowerTest.Length
+            $res.CompletionMatches.Count | Should BeGreaterThan 0
+            $res.CompletionMatches[0].CompletionText | Should Be ".${separator}$oneSubDirTest"
+
+            $res = TabExpansion2 -inputScript $oneSubDirUpperTest -cursorColumn $oneSubDirUpperTest.Length
+            $res.CompletionMatches.Count | Should BeGreaterThan 0
+            $res.CompletionMatches[0].CompletionText | Should Be ".${separator}$oneSubDirTest"
+        }
+
+        It "TabCompletion should be case-sensitive for file names on Unix" -Skip:($IsWindows) {
+            Push-Location -Path $tempDir
+            $res = TabExpansion2 -inputScript $oneSubDirLowerTest -cursorColumn $oneSubDirLowerTest.Length
+            $res.CompletionMatches.Count | Should BeGreaterThan 0
+            $res.CompletionMatches[0].CompletionText | Should BeExactly ".${separator}$oneSubDirTest"
+
+            $res = TabExpansion2 -inputScript $oneSubDirUpperTest -cursorColumn $oneSubDirUpperTest.Length
+            $res.CompletionMatches.Count | Should BeGreaterThan 0
+            $res.CompletionMatches[0].CompletionText | Should BeExactly ".${separator}$oneSubDirTest2"
+        }
+
         It "Input '<inputStr>' should successfully complete" -TestCases $testCases {
             param ($inputStr, $localExpected)
 
@@ -478,8 +511,8 @@ Describe "TabCompletion" -Tags CI {
                 $beforeTab = 'filesystem::{0}\Wind' -f $env:SystemDrive
                 $afterTab = 'filesystem::{0}\Windows' -f $env:SystemDrive
             } else {
-                $beforeTab = 'filesystem::/us' -f $env:SystemDrive
-                $afterTab = 'filesystem::/usr' -f $env:SystemDrive
+                $beforeTab = 'filesystem::/sbi' -f $env:SystemDrive
+                $afterTab = 'filesystem::/sbin' -f $env:SystemDrive
             }
             $res = TabExpansion2 -inputScript $beforeTab -cursorColumn $beforeTab.Length
             $res.CompletionMatches.Count | Should BeGreaterThan 0