python · Dodothereal · Jun 22, 2026
diff --git a/Doc/library/re.rst b/Doc/library/re.rst
@@ -508,9 +508,17 @@ The special characters are:
    Will try to match with ``yes-pattern`` if the group with given *id* or
    *name* exists, and with ``no-pattern`` if it doesn't. ``no-pattern`` is
    optional and can be omitted. For example,
-   ``(<)?(\w+@\w+(?:\.\w+)+)(?(1)>|$)`` is a poor email matching pattern, which
-   will match with ``'<user@host.com>'`` as well as ``'user@host.com'``, but
-   not with ``'<user@host.com'`` nor ``'user@host.com>'``.
+   ``(<)?(\w+@\w+(?:\.\w+)+)(?(1)>|$)`` is a poor email matching pattern,
+   which will match with ``'<user@host.com>'`` as well as ``'user@host.com'``,
+   and will not match with ``'user@host.com>'``.
+
+   Note that when ``yes-pattern`` is not matched while the captured group
+   was set, backtracking clears the capture (the optional group falls
+   back to its no-match state). For example,
+   ``(<)?\w+(?(1)>)`` applied to ``'<3'`` matches only ``'3'`` at
+   position 1 with ``group(1) is None``: the engine first consumes the
+   leading ``<`` to satisfy group 1, fails to match ``>`` at position
+   2, then retries without consuming ``<``.
 
    .. versionchanged:: 3.12
       Group *id* can only contain ASCII digits.

diff --git a/Lib/test/test_re.py b/Lib/test/test_re.py
@@ -706,6 +706,37 @@ def test_re_groupref_exists_errors(self):
         self.checkPatternError(r'()(?(2)a)',
                                "invalid group reference 2", 5)
 
+    def test_re_conditional_drops_capture_on_backtrack(self):
+        # Issue: a captured optional group is cleared when backtracking
+        # causes the ``yes-pattern`` of a (?(id/name)yes|no) construct
+        # to not match after the capture was set. See:
+        # https://github.com/python/cpython/issues/151819
+        # Minimal reproduction from the issue:
+        m = re.search(r'(<)?\w+(?(1)>)', '<3')
+        self.assertEqual(m.group(), '3')
+        self.assertEqual(m.span(), (1, 2))
+        self.assertEqual(m.group(1), None)
+
+        # The successful case keeps the capture intact:
+        m = re.search(r'(<)?\w+(?(1)>)', '<body>')
+        self.assertEqual(m.group(), '<body>')
+        self.assertEqual(m.span(), (0, 6))
+        self.assertEqual(m.group(1), '<')
+
+        # Same effect with ``\w`` style groups and a longer input:
+        m = re.search(r'(<)?[A-Za-z]+(?(1)>)', '<abcXYZ')
+        self.assertEqual(m.group(), 'abcXYZ')
+        self.assertEqual(m.span(), (1, 7))
+        self.assertEqual(m.group(1), None)
+
+        # The pattern documented in Re.rst: with yes-pattern failing
+        # the leading "<" is rerolled.
+        m = re.search(r'(<)?(\w+@\w+(?:\.\w+)+)(?(1)>|$)', '<user@host.com')
+        self.assertEqual(m.group(), 'user@host.com')
+        self.assertEqual(m.span(), (1, 14))
+        self.assertEqual(m.group(1), None)
+        self.assertEqual(m.group(2), 'user@host.com')
+
     def test_re_groupref_exists_validation_bug(self):
         for i in range(256):
             with self.subTest(code=i):

diff --git a/Misc/NEWS.d/next/Documentation/2026-06-22-00-00-00.gh-issue-151819.nULCij.rst b/Misc/NEWS.d/next/Documentation/2026-06-22-00-00-00.gh-issue-151819.nULCij.rst
@@ -0,0 +1,4 @@
+Clarify the :ref:`re-syntax` for ``(?(id/name)yes-pattern|no-pattern)``:
+add a paragraph documenting that backtracking can clear an optional
+capture group whose ``yes-pattern`` fails to match. Also correct the
+embedded example pattern's expected matches.  Issue #151819.