From 027b9378ea78f07bbfb8a579bab04ef403de8d62 Mon Sep 17 00:00:00 2001
From: Jaden Fix <jadenfix20@gmail.com>
Date: Mon, 5 Oct 2026 19:49:40 -0700
Subject: [PATCH 1/2] Fix PostgreSQL JSON operators containing question marks

Signed-off-by: Jaden Fix <jadenfix20@gmail.com>
---
 sqlparse/keywords.py | 4 +++-
 tests/test_format.py | 5 +++++
 tests/test_parse.py  | 4 ++--
 3 files changed, 10 insertions(+), 3 deletions(-)

diff --git a/sqlparse/keywords.py b/sqlparse/keywords.py
index dd6e5d15..8f5260a8 100644
--- a/sqlparse/keywords.py
+++ b/sqlparse/keywords.py
@@ -132,6 +132,8 @@ def find_delimited_spans(text):
     (r"`(``|[^`])*`", tokens.Name),
     (r"´(´´|[^´])*´", tokens.Name),
 
+    # Match unambiguous JSON operators before the single ? placeholder.
+    (r'(\?[|&]|@\?)', tokens.Operator),
     (r'\?', tokens.Name.Placeholder),
     (r'%(\(\w+\))?s', tokens.Name.Placeholder),
     (r'(?<!\w)[$:?]\w+', tokens.Name.Placeholder),
@@ -198,7 +200,7 @@ def find_delimited_spans(text):
     (r'\w[$#\w]*', PROCESS_AS_KEYWORD),
     (r'[;:()\[\],\.]', tokens.Punctuation),
     # JSON operators
-    (r'(\->>?|#>>?|@>|<@|\?\|?|\?&|\-|#\-)', tokens.Operator),
+    (r'(\->>?|#>>?|@>|<@|\-|#\-)', tokens.Operator),
     (r'[<>=~!]+', tokens.Operator.Comparison),
     (r'[+/@#%^&|^-]+', tokens.Operator),
 ]
diff --git a/tests/test_format.py b/tests/test_format.py
index 93495067..4445bac5 100644
--- a/tests/test_format.py
+++ b/tests/test_format.py
@@ -363,6 +363,11 @@ def test_bools(self):
         assert self.formatter(
             sql) == 'select * from table where a && b or c || d'
 
+    @pytest.mark.parametrize('operator', ['?|', '?&', '@?'])
+    def test_json_question_operators(self, operator):
+        sql = f'select data{operator}? from table'
+        assert self.formatter(sql) == f'select data {operator} ? from table'
+
     def test_nested(self):
         sql = 'select *, case when a-b then c end from table'
         assert self.formatter(
diff --git a/tests/test_parse.py b/tests/test_parse.py
index 67168410..3af5d54f 100644
--- a/tests/test_parse.py
+++ b/tests/test_parse.py
@@ -632,8 +632,8 @@ def test_configurable_regex():
 @pytest.mark.parametrize('sql', [
     '->', '->>', '#>', '#>>',
     '@>', '<@',
-    # leaving ? out for now, they're somehow ambiguous as placeholders
-    # '?', '?|', '?&',
+    # A standalone ? remains a placeholder.
+    '?|', '?&', '@?', '@@',
     '||', '-', '#-'
 ])
 def test_json_operators(sql):

From f0687aa96fe19353c72db46e30cd5f137ea4acf9 Mon Sep 17 00:00:00 2001
From: Jaden Fix <jadenfix20@gmail.com>
Date: Mon, 5 Oct 2026 21:27:18 -0700
Subject: [PATCH 2/2] Limit JSON operator fix to unambiguous path operator

Signed-off-by: Jaden Fix <jadenfix20@gmail.com>
---
 sqlparse/keywords.py |  5 ++---
 tests/test_format.py | 12 ++++++++----
 tests/test_parse.py  |  4 ++--
 3 files changed, 12 insertions(+), 9 deletions(-)

diff --git a/sqlparse/keywords.py b/sqlparse/keywords.py
index 8f5260a8..c5c65688 100644
--- a/sqlparse/keywords.py
+++ b/sqlparse/keywords.py
@@ -132,8 +132,7 @@ def find_delimited_spans(text):
     (r"`(``|[^`])*`", tokens.Name),
     (r"´(´´|[^´])*´", tokens.Name),
 
-    # Match unambiguous JSON operators before the single ? placeholder.
-    (r'(\?[|&]|@\?)', tokens.Operator),
+    (r'@\?', tokens.Operator),
     (r'\?', tokens.Name.Placeholder),
     (r'%(\(\w+\))?s', tokens.Name.Placeholder),
     (r'(?<!\w)[$:?]\w+', tokens.Name.Placeholder),
@@ -200,7 +199,7 @@ def find_delimited_spans(text):
     (r'\w[$#\w]*', PROCESS_AS_KEYWORD),
     (r'[;:()\[\],\.]', tokens.Punctuation),
     # JSON operators
-    (r'(\->>?|#>>?|@>|<@|\-|#\-)', tokens.Operator),
+    (r'(\->>?|#>>?|@>|<@|\?\|?|\?&|\-|#\-)', tokens.Operator),
     (r'[<>=~!]+', tokens.Operator.Comparison),
     (r'[+/@#%^&|^-]+', tokens.Operator),
 ]
diff --git a/tests/test_format.py b/tests/test_format.py
index 4445bac5..5253911c 100644
--- a/tests/test_format.py
+++ b/tests/test_format.py
@@ -363,10 +363,14 @@ def test_bools(self):
         assert self.formatter(
             sql) == 'select * from table where a && b or c || d'
 
-    @pytest.mark.parametrize('operator', ['?|', '?&', '@?'])
-    def test_json_question_operators(self, operator):
-        sql = f'select data{operator}? from table'
-        assert self.formatter(sql) == f'select data {operator} ? from table'
+    def test_json_path_operator(self):
+        sql = 'select data@?? from table'
+        assert self.formatter(sql) == 'select data @? ? from table'
+
+    @pytest.mark.parametrize('operator', ['||', '|', '&'])
+    def test_operator_after_placeholder(self, operator):
+        sql = f'select ?{operator}? from table'
+        assert self.formatter(sql) == f'select ? {operator} ? from table'
 
     def test_nested(self):
         sql = 'select *, case when a-b then c end from table'
diff --git a/tests/test_parse.py b/tests/test_parse.py
index 3af5d54f..d1c41624 100644
--- a/tests/test_parse.py
+++ b/tests/test_parse.py
@@ -632,8 +632,8 @@ def test_configurable_regex():
 @pytest.mark.parametrize('sql', [
     '->', '->>', '#>', '#>>',
     '@>', '<@',
-    # A standalone ? remains a placeholder.
-    '?|', '?&', '@?', '@@',
+    # Question-mark prefixes remain ambiguous with placeholders.
+    '@?', '@@',
     '||', '-', '#-'
 ])
 def test_json_operators(sql):