diff --git a/tests/tools/test_search_auto_multiline.py b/tests/tools/test_search_auto_multiline.py
new file mode 100644
index 0000000000000..6183832438380
--- /dev/null
+++ b/tests/tools/test_search_auto_multiline.py
@@ -0,0 +1,51 @@
+"""Tests for search_files auto-multiline routing on \\n patterns."""
+
+import json
+
+import pytest
+
+from tools.file_tools import search_tool
+
+
+@pytest.fixture
+def proj(tmp_path, monkeypatch):
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path / ".hermes"))
+    d = tmp_path / "proj"
+    d.mkdir()
+    (d / "mod.py").write_text(
+        "def setup():\n    init_db()\n    return True\n\n"
+        "def teardown():\n    close_db()\n"
+    )
+    return d
+
+
+class TestAutoMultiline:
+    def test_newline_regex_matches_across_lines(self, proj):
+        r = json.loads(search_tool(r"def setup\(\):\n    init_db\(\)", path=str(proj), task_id="t-ml"))
+        assert "error" not in r
+        assert r["total_count"] >= 1
+        assert "multiline" in r.get("warning", "")
+
+    def test_literal_newline_in_pattern_matches(self, proj):
+        # A raw newline in the pattern (not the \n escape) also routes to
+        # multiline mode. Keep the pattern free of regex metachars.
+        r = json.loads(search_tool("return True\n\ndef teardown", path=str(proj), task_id="t-ml"))
+        assert "error" not in r
+        assert r["total_count"] >= 1
+
+    def test_plain_pattern_unaffected(self, proj):
+        r = json.loads(search_tool("init_db", path=str(proj), task_id="t-ml"))
+        assert r["total_count"] == 1
+        assert "multiline" not in r.get("warning", "")
+
+    def test_escaped_backslash_n_stays_literal(self, proj):
+        # \\n = literal backslash+n search, not a newline: no multiline mode.
+        (proj / "strings.py").write_text('SEP = "a\\\\nb"\n')
+        r = json.loads(search_tool(r"a\\nb", path=str(proj), task_id="t-ml"))
+        assert "error" not in r
+        assert "multiline" not in (r.get("warning") or "")
+
+    def test_multiline_zero_match_is_clean(self, proj):
+        r = json.loads(search_tool(r"def missing\(\):\n    nope\(\)", path=str(proj), task_id="t-ml"))
+        assert "error" not in r
+        assert r["total_count"] == 0
diff --git a/tools/file_operations.py b/tools/file_operations.py
index 5aa4c79fd167a..c3e4ef112dbbe 100644
--- a/tools/file_operations.py
+++ b/tools/file_operations.py
@@ -2478,6 +2478,9 @@ class ShellFileOperations(FileOperations):
         if self._has_command('rg'):
             result = self._search_with_rg(pattern, path, file_glob, limit, offset,
                                           output_mode, context)
+            # rg auto-enables --multiline for \n patterns, so the line-
+            # oriented warning below no longer applies to this engine.
+            return result
         elif self._has_command('grep'):
             result = self._search_with_grep(pattern, path, file_glob, limit, offset,
                                             output_mode, context)
@@ -2506,7 +2509,16 @@ class ShellFileOperations(FileOperations):
                         limit: int, offset: int, output_mode: str, context: int) -> SearchResult:
         """Search using ripgrep."""
         cmd_parts = ["rg", "--line-number", "--no-heading", "--with-filename"]
-        
+
+        # Auto-multiline: a regex `\n` (or a literal newline in the pattern)
+        # cannot match in rg's default line-oriented mode — it used to hard
+        # error ("the literal \"\\n\" is not allowed") and burn a turn. When
+        # the pattern clearly wants to cross lines, enable -U/--multiline
+        # up front and note it in the result.
+        multiline = _pattern_has_regex_newline(pattern)
+        if multiline:
+            cmd_parts.append("--multiline")
+
         # Add context if requested
         if context > 0:
             cmd_parts.extend(["-C", str(context)])
@@ -2556,6 +2568,10 @@ class ShellFileOperations(FileOperations):
 
         # Parse the diagnostic-free payload so error text never becomes a match.
         stdout = payload
+        _ml_note = (
+            "Pattern contains \\n — multiline mode (-U) was enabled automatically "
+            "so the regex can match across line boundaries."
+        ) if multiline else None
         # Parse results based on output mode
         if output_mode == "files_only":
             all_files = [f for f in stdout.strip().split('\n') if f]
@@ -2566,6 +2582,7 @@ class ShellFileOperations(FileOperations):
                 total_count=total,
                 truncated=bool(limit_reason),
                 limit_reason=limit_reason,
+                warning=_ml_note,
             )
         
         elif output_mode == "count":
@@ -2626,6 +2643,7 @@ class ShellFileOperations(FileOperations):
                 total_count=total,
                 truncated=total > offset + limit or bool(limit_reason),
                 limit_reason=limit_reason,
+                warning=_ml_note,
             )
     
     def _search_with_grep(self, pattern: str, path: str, file_glob: Optional[str],