diff --git a/tests/tools/test_search_error_guard.py b/tests/tools/test_search_error_guard.py
index aa76dba6cc3..e045c8c3d52 100644
--- a/tests/tools/test_search_error_guard.py
+++ b/tests/tools/test_search_error_guard.py
@@ -28,6 +28,7 @@ import pytest
 
 from tools.file_operations import (
     ShellFileOperations,
+    _pattern_has_regex_newline,
     _split_tool_diagnostics,
 )
 from tools.environments.local import LocalEnvironment
@@ -124,6 +125,63 @@ class TestSearchErrorGuard:
         assert res.total_count >= 4
 
 
+class TestSearchContentNewlineWarning:
+    def test_odd_backslash_n_is_detected_as_regex_newline(self):
+        assert _pattern_has_regex_newline(r"needle\n")
+        assert _pattern_has_regex_newline(r"needle\\\n")
+
+    def test_even_backslash_n_is_literal_and_not_detected(self):
+        assert not _pattern_has_regex_newline(r"needle\\n")
+        assert not _pattern_has_regex_newline(r"needle\\\\n")
+
+    def test_zero_matches_with_regex_newline_adds_warning_not_error(self, match_tree):
+        res = _ops(match_tree).search(
+            r"absent\npattern",
+            path=str(match_tree),
+            target="content",
+            context=2,
+        )
+
+        assert res.error is None
+        assert res.total_count == 0
+        assert res.warning is not None
+        assert "0 results found" in res.warning
+        assert "-U/--multiline" in res.warning
+
+    def test_actual_newline_pattern_adds_warning_not_error(self, match_tree):
+        res = _ops(match_tree).search(
+            "absent\npattern",
+            path=str(match_tree),
+            target="content",
+        )
+
+        assert res.error is None
+        assert res.total_count == 0
+        assert res.warning is not None
+
+    def test_search_with_matching_alternative_and_regex_newline_warns(self, match_tree):
+        res = _ops(match_tree).search(
+            r"needle|absent\npattern",
+            path=str(match_tree),
+            target="content",
+        )
+
+        assert res.error is None
+        assert res.total_count == 0
+        assert res.warning is not None
+
+    def test_literal_backslash_n_pattern_does_not_warn(self, match_tree):
+        res = _ops(match_tree).search(
+            r"absent\\npattern",
+            path=str(match_tree),
+            target="content",
+        )
+
+        assert res.error is None
+        assert res.total_count == 0
+        assert res.warning is None
+
+
 class TestSplitToolDiagnostics:
     """Unit coverage for the shape-based diagnostic/payload splitter."""
 
diff --git a/tools/file_operations.py b/tools/file_operations.py
index c9374a4eff9..78bdd8d63ca 100644
--- a/tools/file_operations.py
+++ b/tools/file_operations.py
@@ -242,6 +242,7 @@ class SearchResult:
     total_count: int = 0
     truncated: bool = False
     limit_reason: Optional[str] = None
+    warning: Optional[str] = None
     error: Optional[str] = None
     
     # Densify content-mode matches into a path-grouped text block above this
@@ -302,6 +303,8 @@ class SearchResult:
             result["truncated"] = True
         if self.limit_reason:
             result["limit_reason"] = self.limit_reason
+        if self.warning:
+            result["warning"] = self.warning
         if self.error:
             result["error"] = self.error
         return result
@@ -719,6 +722,45 @@ def normalize_search_pagination(offset: Any = DEFAULT_SEARCH_OFFSET,
     return normalized_offset, normalized_limit
 
 
+_REGEX_NEWLINE_ESCAPE_RE = re.compile(r"(?<!\\)(?:\\\\)*\\n")
+
+
+def _pattern_has_regex_newline(pattern: str) -> bool:
+    """Return True when a content-search regex tries to match a newline.
+
+    ``search_files`` runs rg/grep in line-oriented mode, not rg
+    ``-U``/``--multiline`` mode, so newline regexes cannot match across
+    lines.  Detect both a literal newline already decoded into the tool
+    argument and a regex ``\n`` escape (odd number of backslashes before
+    ``n``).  Even backslashes, e.g. ``\\n``, mean a literal backslash+n
+    search and should not warn.
+    """
+    return "\n" in pattern or bool(_REGEX_NEWLINE_ESCAPE_RE.search(pattern))
+
+
+def _is_line_oriented_newline_error(error: Optional[str]) -> bool:
+    """Return True for rg's hard error when multiline mode is required."""
+    if not error:
+        return False
+    return "literal \"\\n\" is not allowed" in error and "--multiline" in error
+
+
+def _maybe_warn_line_oriented_newline_pattern(result: SearchResult, pattern: str) -> SearchResult:
+    """Attach a newline-regex warning only when search found no usable results."""
+    if result.total_count != 0 or not _pattern_has_regex_newline(pattern):
+        return result
+    if result.error and not _is_line_oriented_newline_error(result.error):
+        return result
+    result.error = None
+    result.warning = (
+        "0 results found. Note: search_files content search is line-oriented "
+        "and does not run ripgrep with -U/--multiline, so `\\n` in the regex "
+        "does not match line breaks. Use context=N to inspect neighboring "
+        "lines, or escape as `\\\\n` when searching for a literal backslash+n."
+    )
+    return result
+
+
 class ShellFileOperations(FileOperations):
     """
     File operations implemented via shell commands.
@@ -2117,17 +2159,19 @@ class ShellFileOperations(FileOperations):
         """Search for content inside files (grep-like)."""
         # Try ripgrep first (fast), fallback to grep (slower but works)
         if self._has_command('rg'):
-            return self._search_with_rg(pattern, path, file_glob, limit, offset, 
-                                        output_mode, context)
-        elif self._has_command('grep'):
-            return self._search_with_grep(pattern, path, file_glob, limit, offset,
+            result = self._search_with_rg(pattern, path, file_glob, limit, offset,
                                           output_mode, context)
+        elif self._has_command('grep'):
+            result = self._search_with_grep(pattern, path, file_glob, limit, offset,
+                                            output_mode, context)
         else:
             # Neither rg nor grep available (Windows without Git Bash, etc.)
             return SearchResult(
                 error="Content search requires ripgrep (rg) or grep. "
                       "Install ripgrep: https://github.com/BurntSushi/ripgrep#installation"
             )
+
+        return _maybe_warn_line_oriented_newline_pattern(result, pattern)
     
     def _search_with_rg(self, pattern: str, path: str, file_glob: Optional[str],
                         limit: int, offset: int, output_mode: str, context: int) -> SearchResult:
diff --git a/tools/file_tools.py b/tools/file_tools.py
index 42b6153cb95..1fc778e0d6c 100644
--- a/tools/file_tools.py
+++ b/tools/file_tools.py
@@ -1595,7 +1595,7 @@ PATCH_SCHEMA = {
 
 SEARCH_FILES_SCHEMA = {
     "name": "search_files",
-    "description": "Search file contents or find files by name. Use this instead of grep/rg/find/ls in terminal. Ripgrep-backed, faster than shell equivalents.\n\nContent search (target='content'): Regex search inside files. Output modes: full matches with line numbers, file paths only, or match counts. Content search is line-oriented: do not put \\n in regex patterns (even inside alternation); use context to inspect neighboring lines.\n\nFile search (target='files'): Find files by glob pattern (e.g., '*.py', '*config*'). Also use this instead of ls — results sorted by modification time.",
+    "description": "Search file contents or find files by name. Use this instead of grep/rg/find/ls in terminal. Ripgrep-backed, faster than shell equivalents.\n\nContent search (target='content'): Regex search inside files. Output modes: full matches with line numbers, file paths only, or match counts.\n\nFile search (target='files'): Find files by glob pattern (e.g., '*.py', '*config*'). Also use this instead of ls — results sorted by modification time.",
     "parameters": {
         "type": "object",
         "properties": {