diff --git a/Lib/ntpath.py b/Lib/ntpath.py
index ee1a2157a14..6732aa22cb1 100644
--- a/Lib/ntpath.py
+++ b/Lib/ntpath.py
@@ -386,7 +386,7 @@ def expandvars(path):
                 index = path.index(c)
                 res += c + path[:index + 1]
             except ValueError:
-                res += path
+                res += c + path
                 index = pathlen - 1
         elif c == percent:  # variable or '%'
             if path[index + 1:index + 2] == percent:
diff --git a/Lib/test/test_ntpath.py b/Lib/test/test_ntpath.py
index c8d84a7467c..dacddded3dd 100644
--- a/Lib/test/test_ntpath.py
+++ b/Lib/test/test_ntpath.py
@@ -237,6 +237,7 @@ def test_expandvars(self):
             tester('ntpath.expandvars("%?bar%")', "%?bar%")
             tester('ntpath.expandvars("%foo%%bar")', "bar%bar")
             tester('ntpath.expandvars("\'%foo%\'%bar")', "\'%foo%\'%bar")
+            tester('ntpath.expandvars("bar\'%foo%")', "bar\'%foo%")
 
     @unittest.skipUnless(support.FS_NONASCII, 'need support.FS_NONASCII')
     def test_expandvars_nonascii(self):
diff --git a/Misc/NEWS b/Misc/NEWS
index 6534443f07b..822e3fdf918 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -30,6 +30,8 @@ Core and Builtins
 Library
 -------
 
+- Issue #23742: ntpath.expandvars() no longer loses unbalanced single quotes.
+
 - Issue #21717: The zipfile.ZipFile.open function now supports 'x' (exclusive
   creation) mode.