diff --git a/Lib/tarfile.py b/Lib/tarfile.py
index 7db3a40c9b33cf..9b0b66a21cb13c 100644
--- a/Lib/tarfile.py
+++ b/Lib/tarfile.py
@@ -2438,7 +2438,7 @@ def extractall(self, path=".", members=None, *, numeric_owner=False,
                     continue
                 dirpath = os.path.join(path, tarinfo.name)
                 try:
-                    lstat = os.lstat(dirpath)
+                    lstat = os.lstat(dirpath.replace(r'/', os.sep))
                 except FileNotFoundError:
                     self._log_no_directory_fixup(tarinfo, 'missing')
                     continue
diff --git a/Misc/NEWS.d/next/Library/2026-01-10-17-39-09.gh-issue-143663.9LEFAf.rst b/Misc/NEWS.d/next/Library/2026-01-10-17-39-09.gh-issue-143663.9LEFAf.rst
new file mode 100644
index 00000000000000..562258bda17eff
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-01-10-17-39-09.gh-issue-143663.9LEFAf.rst
@@ -0,0 +1 @@
+:mod:`tarfile`: :meth:`TarFile.extractall` now uses OS-specific separators to call lstat. This fixes a failure case with raw Win32 paths on Windows.