diff --git a/tests/sentry/issues/ownership/test_grammar.py b/tests/sentry/issues/ownership/test_grammar.py
index 6638c50242d0f3..dda89081341946 100644
--- a/tests/sentry/issues/ownership/test_grammar.py
+++ b/tests/sentry/issues/ownership/test_grammar.py
@@ -1185,3 +1185,62 @@ def test_codeowners_leading_slash_matching(
     pattern: str, path_details: Sequence[Mapping[str, str]], expected: bool
 ) -> None:
     _assert_matcher(Matcher("codeowners", pattern), path_details, expected)
+
+
+@pytest.mark.parametrize(
+    "pattern, path_details, expected",
+    [
+        # These should NOT match - they contain "example.py" as a suffix but
+        # the filename is not exactly "example.py"
+        (
+            "/**/example.py",
+            [{"filename": "/src/bad_example.py"}, {"abs_path": "/src/bad_example.py"}],
+            False,
+        ),
+        (
+            "/**/example.py",
+            [{"filename": "/src/foo/bad_example.py"}, {"abs_path": "/src/foo/bad_example.py"}],
+            False,
+        ),
+        (
+            "/**/example.py",
+            [{"filename": "/src/my_example.py"}, {"abs_path": "/src/my_example.py"}],
+            False,
+        ),
+        (
+            "/**/example.py",
+            [
+                {"filename": "/src/voice/calls/inbound/bad_example.py"},
+                {"abs_path": "/src/voice/calls/inbound/bad_example.py"},
+            ],
+            False,
+        ),
+        (
+            "/**/example.py",
+            [{"filename": "/src/good_example.py"}, {"abs_path": "/src/good_example.py"}],
+            False,
+        ),
+        (
+            "/**/example.py",
+            [{"filename": "/src/test_example.py"}, {"abs_path": "/src/test_example.py"}],
+            False,
+        ),
+        (
+            "**/example.py",
+            [{"filename": "/src/example.py"}, {"abs_path": "/src/example.py"}],
+            True,
+        ),
+        (
+            "**/example.py",
+            [{"filename": "/src/bad_example.py"}, {"abs_path": "/src/bad_example.py"}],
+            False,
+        ),
+    ],
+)
+def test_codeowners_double_star_matching(
+    pattern: str, path_details: Sequence[Mapping[str, str]], expected: bool
+) -> None:
+    """
+    "/**/example.py" pattern should only match files named exactly "example.py" at any directory depth.
+    """
+    _assert_matcher(Matcher("codeowners", pattern), path_details, expected)