diff --git a/changelog.md b/changelog.md
index b961d394..1e333ee4 100644
--- a/changelog.md
+++ b/changelog.md
@@ -6,6 +6,11 @@ Features
 * Right-align numeric columns, and make the behavior configurable.
 
 
+Bug Fixes
+--------
+* Better respect case when `keyword_casing` is `auto`.
+
+
 1.47.0 (2026/01/24)
 ==============
 
diff --git a/mycli/sqlcompleter.py b/mycli/sqlcompleter.py
index 4834d22c..3d20ffeb 100644
--- a/mycli/sqlcompleter.py
+++ b/mycli/sqlcompleter.py
@@ -1027,7 +1027,7 @@ def find_matches(
                     completions.append(item)
 
         if casing == "auto":
-            casing = "lower" if last and last[-1].islower() else "upper"
+            casing = "lower" if last and (last[0].islower() or last[-1].islower()) else "upper"
 
         def apply_case(kw: str) -> str:
             if casing == "upper":
diff --git a/test/test_smart_completion_public_schema_only.py b/test/test_smart_completion_public_schema_only.py
index 30aba328..ae220b0a 100644
--- a/test/test_smart_completion_public_schema_only.py
+++ b/test/test_smart_completion_public_schema_only.py
@@ -544,3 +544,15 @@ def test_file_name_completion(completer, complete_event, text, expected):
     result = list(completer.get_completions(Document(text=text, cursor_position=position), complete_event))
     expected = [Completion(txt, pos) for txt, pos in expected]
     assert result == expected
+
+
+def test_auto_case_heuristic(completer, complete_event):
+    text = "select jon_"
+    position = len("select jon_")
+    result = list(completer.get_completions(Document(text=text, cursor_position=position), complete_event))
+    assert [x.text for x in result] == [
+        'json_table',
+        'json_value',
+        'join',
+        'json',
+    ]