diff --git a/Lib/distutils/filelist.py b/Lib/distutils/filelist.py
index a80c71e8c77..58a2bfb108f 100644
--- a/Lib/distutils/filelist.py
+++ b/Lib/distutils/filelist.py
@@ -289,7 +289,8 @@ def glob_to_re(pattern):
     # character except the special characters.
     # XXX currently the "special characters" are just slash -- i.e. this is
     # Unix-only.
-    pattern_re = re.sub(r'(^|[^\\])\.', r'\1[^/]', pattern_re)
+    pattern_re = re.sub(r'((?<!\\)(\\\\)*)\.', r'\1[^/]', pattern_re)
+
     return pattern_re
 
 
diff --git a/Lib/distutils/tests/test_filelist.py b/Lib/distutils/tests/test_filelist.py
new file mode 100644
index 00000000000..86db5574410
--- /dev/null
+++ b/Lib/distutils/tests/test_filelist.py
@@ -0,0 +1,23 @@
+"""Tests for distutils.filelist."""
+import unittest
+from distutils.filelist import glob_to_re
+
+class FileListTestCase(unittest.TestCase):
+
+    def test_glob_to_re(self):
+        # simple cases
+        self.assertEquals(glob_to_re('foo*'), 'foo[^/]*$')
+        self.assertEquals(glob_to_re('foo?'), 'foo[^/]$')
+        self.assertEquals(glob_to_re('foo??'), 'foo[^/][^/]$')
+
+        # special cases
+        self.assertEquals(glob_to_re(r'foo\\*'), r'foo\\\\[^/]*$')
+        self.assertEquals(glob_to_re(r'foo\\\*'), r'foo\\\\\\[^/]*$')
+        self.assertEquals(glob_to_re('foo????'), r'foo[^/][^/][^/][^/]$')
+        self.assertEquals(glob_to_re(r'foo\\??'), r'foo\\\\[^/][^/]$')
+
+def test_suite():
+    return unittest.makeSuite(FileListTestCase)
+
+if __name__ == "__main__":
+    unittest.main(defaultTest="test_suite")
diff --git a/Misc/NEWS b/Misc/NEWS
index cac482b1989..815081b1e7a 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -327,6 +327,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #1491431: Fixed distutils.filelist.glob_to_re for edge cases.
+  Initial fix by Wayne Davison.
+
 - Issue #5694: removed spurious test output in Distutils (test_clean).
 
 - Issue #1326077: fix the formatting of SyntaxErrors by the traceback module.