diff --git a/src/Runner.Common/HostContext.cs b/src/Runner.Common/HostContext.cs
index ffb08684a..1dff2d706 100644
--- a/src/Runner.Common/HostContext.cs
+++ b/src/Runner.Common/HostContext.cs
@@ -392,6 +392,7 @@ namespace GitHub.Runner.Common
 
                 case WellKnownDirectory.Root:
                     path = new DirectoryInfo(GetDirectory(WellKnownDirectory.Bin)).Parent.FullName;
+                    path = PathUtil.GetCanonicalPath(path);
                     break;
 
                 case WellKnownDirectory.Temp:
diff --git a/src/Runner.Sdk/Util/PathUtil.cs b/src/Runner.Sdk/Util/PathUtil.cs
index 98bf82d05..3d6004934 100644
--- a/src/Runner.Sdk/Util/PathUtil.cs
+++ b/src/Runner.Sdk/Util/PathUtil.cs
@@ -1,4 +1,7 @@
 using System.IO;
+using System.Runtime.InteropServices;
+using System.Text;
+using Microsoft.Win32.SafeHandles;
 
 namespace GitHub.Runner.Sdk
 {
@@ -6,8 +9,82 @@ namespace GitHub.Runner.Sdk
     {
 #if OS_WINDOWS
         public static readonly string PathVariable = "Path";
+
+        [DllImport("kernel32.dll", SetLastError = true, CharSet = CharSet.Unicode)]
+        private static extern SafeFileHandle CreateFile(
+            string lpFileName,
+            uint dwDesiredAccess,
+            uint dwShareMode,
+            System.IntPtr lpSecurityAttributes,
+            uint dwCreationDisposition,
+            uint dwFlagsAndAttributes,
+            System.IntPtr hTemplateFile);
+
+        [DllImport("kernel32.dll", SetLastError = true, CharSet = CharSet.Unicode)]
+        private static extern uint GetFinalPathNameByHandle(
+            SafeFileHandle hFile,
+            [Out] StringBuilder lpszFilePath,
+            uint cchFilePath,
+            uint dwFlags);
+
+        private const uint FILE_READ_ATTRIBUTES = 0x80;
+        private const uint FILE_SHARE_READ = 0x1;
+        private const uint FILE_SHARE_WRITE = 0x2;
+        private const uint FILE_SHARE_DELETE = 0x4;
+        private const uint OPEN_EXISTING = 3;
+        private const uint FILE_FLAG_BACKUP_SEMANTICS = 0x02000000;
+        private const uint VOLUME_NAME_DOS = 0x0;
+
+        /// <summary>
+        /// Returns the NTFS canonical path for a directory, resolving drive letter
+        /// and folder name casing to match what is stored on disk.
+        /// On non-Windows platforms, returns the path unchanged.
+        /// </summary>
+        public static string GetCanonicalPath(string path)
+        {
+            if (string.IsNullOrEmpty(path) || !Directory.Exists(path))
+            {
+                return path;
+            }
+
+            using var handle = CreateFile(
+                path,
+                FILE_READ_ATTRIBUTES,
+                FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE,
+                System.IntPtr.Zero,
+                OPEN_EXISTING,
+                FILE_FLAG_BACKUP_SEMANTICS,
+                System.IntPtr.Zero);
+
+            if (handle.IsInvalid)
+            {
+                return path;
+            }
+
+            var buffer = new StringBuilder(1024);
+            var result = GetFinalPathNameByHandle(handle, buffer, (uint)buffer.Capacity, VOLUME_NAME_DOS);
+            if (result == 0 || result > buffer.Capacity)
+            {
+                return path;
+            }
+
+            var canonicalPath = buffer.ToString();
+
+            // Strip the \\?\ prefix that GetFinalPathNameByHandle adds
+            if (canonicalPath.StartsWith(@"\\?\"))
+            {
+                canonicalPath = canonicalPath.Substring(4);
+            }
+
+            return canonicalPath;
+        }
 #else
         public static readonly string PathVariable = "PATH";
+
+        public static string GetCanonicalPath(string path)
+        {
+            return path;
+        }
 #endif
 
         public static string PrependPath(string path, string currentPath)
diff --git a/src/Test/L0/Util/PathUtilL0.cs b/src/Test/L0/Util/PathUtilL0.cs
new file mode 100644
index 000000000..787f5abf6
--- /dev/null
+++ b/src/Test/L0/Util/PathUtilL0.cs
@@ -0,0 +1,79 @@
+using GitHub.Runner.Sdk;
+using System.IO;
+using System.Runtime.InteropServices;
+using Xunit;
+
+namespace GitHub.Runner.Common.Tests.Util
+{
+    public sealed class PathUtilL0
+    {
+        [Fact]
+        [Trait("Level", "L0")]
+        [Trait("Category", "Common")]
+        public void GetCanonicalPath_ReturnsPath_WhenDirectoryDoesNotExist()
+        {
+            var fakePath = Path.Combine(Path.GetTempPath(), "nonexistent_" + Path.GetRandomFileName());
+            var result = PathUtil.GetCanonicalPath(fakePath);
+            Assert.Equal(fakePath, result);
+        }
+
+        [Fact]
+        [Trait("Level", "L0")]
+        [Trait("Category", "Common")]
+        public void GetCanonicalPath_ReturnsPath_WhenNull()
+        {
+            Assert.Null(PathUtil.GetCanonicalPath(null));
+        }
+
+        [Fact]
+        [Trait("Level", "L0")]
+        [Trait("Category", "Common")]
+        public void GetCanonicalPath_ReturnsEmpty_WhenEmpty()
+        {
+            Assert.Equal(string.Empty, PathUtil.GetCanonicalPath(string.Empty));
+        }
+
+        [Fact]
+        [Trait("Level", "L0")]
+        [Trait("Category", "Common")]
+        public void GetCanonicalPath_ReturnsValidPath_ForExistingDirectory()
+        {
+            var tempDir = Path.Combine(Path.GetTempPath(), "pathutil_test_" + Path.GetRandomFileName());
+            try
+            {
+                Directory.CreateDirectory(tempDir);
+                var result = PathUtil.GetCanonicalPath(tempDir);
+                Assert.NotNull(result);
+                Assert.True(Directory.Exists(result));
+            }
+            finally
+            {
+                if (Directory.Exists(tempDir))
+                {
+                    Directory.Delete(tempDir);
+                }
+            }
+        }
+
+#if OS_WINDOWS
+        [Fact]
+        [Trait("Level", "L0")]
+        [Trait("Category", "Common")]
+        public void GetCanonicalPath_NormalizesDriveLetter_OnWindows()
+        {
+            // The temp directory should always have an uppercase drive letter
+            // when resolved through GetFinalPathNameByHandle
+            var tempDir = Path.GetTempPath().TrimEnd(Path.DirectorySeparatorChar);
+
+            // Force lowercase drive letter
+            var lowerCased = char.ToLower(tempDir[0]) + tempDir.Substring(1);
+
+            var result = PathUtil.GetCanonicalPath(lowerCased);
+
+            // The canonical path should have an uppercase drive letter
+            Assert.True(char.IsUpper(result[0]),
+                $"Expected uppercase drive letter but got: {result}");
+        }
+#endif
+    }
+}