diff --git a/tests/tools/test_fuzzy_match.py b/tests/tools/test_fuzzy_match.py
index 9db45b7a5..3f7d31582 100644
--- a/tests/tools/test_fuzzy_match.py
+++ b/tests/tools/test_fuzzy_match.py
@@ -262,3 +262,70 @@ class TestFindClosestLines:
         # Should include line numbers in format "N| content"
         assert "|" in result
 
+
+class TestFormatNoMatchHint:
+    """Gating tests for format_no_match_hint — the shared helper that decides
+    whether a 'Did you mean?' snippet should be appended to an error.
+    """
+
+    def setup_method(self):
+        from tools.fuzzy_match import format_no_match_hint
+        self.fmt = format_no_match_hint
+
+    def test_fires_on_could_not_find_with_match(self):
+        """Classic no-match: similar content exists → hint fires."""
+        content = "def foo():\n    pass\ndef bar():\n    pass\n"
+        result = self.fmt(
+            "Could not find a match for old_string in the file",
+            0, "def baz():", content,
+        )
+        assert "Did you mean" in result
+        assert "foo" in result or "bar" in result
+
+    def test_silent_on_ambiguous_match_error(self):
+        """'Found N matches' is not a missing-match failure — no hint."""
+        content = "aaa bbb aaa\n"
+        result = self.fmt(
+            "Found 2 matches for old_string. Provide more context to make it unique, or use replace_all=True.",
+            0, "aaa", content,
+        )
+        assert result == ""
+
+    def test_silent_on_escape_drift_error(self):
+        """Escape-drift errors are intentional blocks — hint would mislead."""
+        content = "x = 1\n"
+        result = self.fmt(
+            "Escape-drift detected: old_string and new_string contain the literal sequence '\\\\''...",
+            0, "x = \\'1\\'", content,
+        )
+        assert result == ""
+
+    def test_silent_on_identical_strings(self):
+        """old_string == new_string — hint irrelevant."""
+        result = self.fmt(
+            "old_string and new_string are identical",
+            0, "foo", "foo bar\n",
+        )
+        assert result == ""
+
+    def test_silent_when_match_count_nonzero(self):
+        """If match succeeded, we shouldn't be in the error path — defense in depth."""
+        result = self.fmt(
+            "Could not find a match for old_string in the file",
+            1, "foo", "foo bar\n",
+        )
+        assert result == ""
+
+    def test_silent_on_none_error(self):
+        """No error at all — no hint."""
+        result = self.fmt(None, 0, "foo", "bar\n")
+        assert result == ""
+
+    def test_silent_when_no_similar_content(self):
+        """Even for a valid no-match error, skip hint when nothing similar exists."""
+        result = self.fmt(
+            "Could not find a match for old_string in the file",
+            0, "totally_unique_xyzzy_qux", "abc\nxyz\n",
+        )
+        assert result == ""
+
diff --git a/tools/file_operations.py b/tools/file_operations.py
index c9b5d3d64..87ad13968 100644
--- a/tools/file_operations.py
+++ b/tools/file_operations.py
@@ -741,10 +741,8 @@ class ShellFileOperations(FileOperations):
         if error or match_count == 0:
             err_msg = error or f"Could not find match for old_string in {path}"
             try:
-                from tools.fuzzy_match import find_closest_lines
-                hint = find_closest_lines(old_string, content)
-                if hint:
-                    err_msg += "\n\nDid you mean one of these sections?\n" + hint
+                from tools.fuzzy_match import format_no_match_hint
+                err_msg += format_no_match_hint(err_msg, match_count, old_string, content)
             except Exception:
                 pass
             return PatchResult(error=err_msg)
diff --git a/tools/file_tools.py b/tools/file_tools.py
index af6701f82..5b44ff03d 100644
--- a/tools/file_tools.py
+++ b/tools/file_tools.py
@@ -670,8 +670,11 @@ def patch_tool(mode: str = "replace", path: str = None, old_string: str = None,
         result_json = json.dumps(result_dict, ensure_ascii=False)
         # Hint when old_string not found — saves iterations where the agent
         # retries with stale content instead of re-reading the file.
+        # Suppressed when patch_replace already attached a rich "Did you mean?"
+        # snippet (which is strictly more useful than the generic hint).
         if result_dict.get("error") and "Could not find" in str(result_dict["error"]):
-            result_json += "\n\n[Hint: old_string not found. Use read_file to verify the current content, or search_files to locate the text.]"
+            if "Did you mean one of these sections?" not in str(result_dict["error"]):
+                result_json += "\n\n[Hint: old_string not found. Use read_file to verify the current content, or search_files to locate the text.]"
         return result_json
     except Exception as e:
         return tool_error(str(e))
diff --git a/tools/fuzzy_match.py b/tools/fuzzy_match.py
index 301794644..9a922cd9b 100644
--- a/tools/fuzzy_match.py
+++ b/tools/fuzzy_match.py
@@ -681,3 +681,24 @@ def find_closest_lines(old_string: str, content: str, context_lines: int = 2, ma
         return ""
 
     return "\n---\n".join(parts)
+
+
+def format_no_match_hint(error: Optional[str], match_count: int,
+                         old_string: str, content: str) -> str:
+    """Return a '\\n\\nDid you mean...' snippet for plain no-match errors.
+
+    Gated so the hint only fires for actual "old_string not found" failures.
+    Ambiguous-match ("Found N matches"), escape-drift, and identical-strings
+    errors all have ``match_count == 0`` but a "did you mean?" snippet would
+    be misleading — those failed for unrelated reasons.
+
+    Returns an empty string when there's nothing useful to append.
+    """
+    if match_count != 0:
+        return ""
+    if not error or not error.startswith("Could not find"):
+        return ""
+    hint = find_closest_lines(old_string, content)
+    if not hint:
+        return ""
+    return "\n\nDid you mean one of these sections?\n" + hint
diff --git a/tools/patch_parser.py b/tools/patch_parser.py
index 0c961083c..d2a298fc9 100644
--- a/tools/patch_parser.py
+++ b/tools/patch_parser.py
@@ -290,10 +290,16 @@ def _validate_operations(
                 )
                 if count == 0:
                     label = f"'{hunk.context_hint}'" if hunk.context_hint else "(no hint)"
-                    errors.append(
+                    msg = (
                         f"{op.file_path}: hunk {label} not found"
                         + (f" — {match_error}" if match_error else "")
                     )
+                    try:
+                        from tools.fuzzy_match import format_no_match_hint
+                        msg += format_no_match_hint(match_error, count, search_pattern, simulated)
+                    except Exception:
+                        pass
+                    errors.append(msg)
                 else:
                     # Advance simulation so subsequent hunks validate correctly.
                     # Reuse the result from the call above — no second fuzzy run.
@@ -537,7 +543,13 @@ def _apply_update(op: PatchOperation, file_ops: Any) -> Tuple[bool, str]:
                             error = None
                 
                 if error:
-                    return False, f"Could not apply hunk: {error}"
+                    err_msg = f"Could not apply hunk: {error}"
+                    try:
+                        from tools.fuzzy_match import format_no_match_hint
+                        err_msg += format_no_match_hint(error, 0, search_pattern, new_content)
+                    except Exception:
+                        pass
+                    return False, err_msg
         else:
             # Addition-only hunk (no context or removed lines).
             # Insert at the location indicated by the context hint, or at end of file.
diff --git a/tools/skill_manager_tool.py b/tools/skill_manager_tool.py
index 33d3976ea..493b434c5 100644
--- a/tools/skill_manager_tool.py
+++ b/tools/skill_manager_tool.py
@@ -449,9 +449,15 @@ def _patch_skill(
     if match_error:
         # Show a short preview of the file so the model can self-correct
         preview = content[:500] + ("..." if len(content) > 500 else "")
+        err_msg = match_error
+        try:
+            from tools.fuzzy_match import format_no_match_hint
+            err_msg += format_no_match_hint(match_error, match_count, old_string, content)
+        except Exception:
+            pass
         return {
             "success": False,
-            "error": match_error,
+            "error": err_msg,
             "file_preview": preview,
         }