fix(uploads): preserve separate bold spans in outline titles (#7150)

README.md

@@ -2638,6 +2638,8 @@ removing the worker's temporary source. Automatic conversion remains off by defa
 
 Uploaded Markdown outlines recognize ATX heading syntax, clean closing markers with a linear suffix scan, and skip HTML comment blocks and fenced and indented code examples, so hashtags and code comments do not
 crowd out real document sections from the agent's heading preview. Indented bold examples are also excluded; PDF-style bold headings with up to three leading spaces remain supported.
+Whole-title bold wrappers and adjacent PDF bold spans are cleaned; separate bold
+spans joined by ordinary text retain their markers instead of losing only the outer pair.
 Split-bold numeric table rows, including parenthesized years, signed values, and
 currency-prefixed amounts, are excluded when any block after the section number
 is a numeric column, so they do not consume the outline's heading budget.

backend/packages/harness/deerflow/utils/file_outline.py

@@ -73,7 +73,8 @@ def _clean_bold_title(raw: str) -> str:
 
     pymupdf4llm sometimes emits adjacent bold spans as ``**A** **B**`` instead
     of a single ``**A B**`` block.  This helper merges those fragments and then
-    strips the outermost ``**...**`` wrapper so the caller gets plain text.
+    strips a whole-title ``**...**`` wrapper. Mixed bold/plain text keeps its
+    delimiters rather than losing the ends of separate spans.
 
     Examples::
 
@@ -83,9 +84,10 @@ def _clean_bold_title(raw: str) -> str:
     """
     # Merge adjacent bold spans: "** **" → " "
     merged = re.sub(r"\*\*\s*\*\*", " ", raw).strip()
-    # Strip outermost **...** if the whole string is wrapped
+    # Strip one whole-title wrapper, not the ends of separate bold spans.
     if m := re.fullmatch(r"\*\*(.+?)\*\*", merged, re.DOTALL):
-        return m.group(1).strip()
+        if "**" not in m.group(1):
+            return m.group(1).strip()
     return merged
 
 

backend/tests/test_file_outline_bold_wrappers.py

@@ -0,0 +1,37 @@
+"""Mixed bold spans must not be mistaken for a whole-title wrapper."""
+
+from pathlib import Path
+
+import pytest
+
+from deerflow.uploads.companions import register_companion
+from deerflow.utils.file_outline import extract_outline_for_file
+
+
+@pytest.mark.parametrize(
+    ("heading", "title"),
+    [
+        ("**Revenue** and **Profit**", "**Revenue** and **Profit**"),
+        ("**收入**与**利润**", "**收入**与**利润**"),
+        ("**Before** / **After**", "**Before** / **After**"),
+        ("**Overview**", "Overview"),
+        ("**UNITED STATES** **SECURITIES**", "UNITED STATES SECURITIES"),
+        ("**A**\t**B**", "A B"),
+        ("Revenue and **Profit**", "Revenue and **Profit**"),
+        ("**Revenue** and Profit", "**Revenue** and Profit"),
+        ("Plain title", "Plain title"),
+    ],
+)
+@pytest.mark.parametrize("converted", [False, True])
+def test_upload_outline_only_unwraps_a_whole_bold_title(tmp_path: Path, heading: str, title: str, converted: bool) -> None:
+    markdown = tmp_path / "report.md"
+    original = f"Introduction\r\n\r\n## {heading} ###\r\n# Next section\r\n".encode()
+    markdown.write_bytes(original)
+    source = markdown
+    if converted:
+        source = tmp_path / "report.pdf"
+        source.write_bytes(b"synthetic source; conversion not invoked")
+        register_companion(source, markdown)
+
+    assert extract_outline_for_file(source) == ([{"title": title, "line": 3}, {"title": "Next section", "line": 4}], [])
+    assert markdown.read_bytes() == original

backend/tests/test_list_uploaded_files_tool.py

@@ -83,6 +83,14 @@ class TestFormatOmittedSummary:
 
 
 class TestListUploadedFiles:
+    def test_outline_preserves_separate_bold_spans(self, tmp_path):
+        uploads_dir = _uploads_dir(tmp_path)
+        (uploads_dir / "report.md").write_text("# **Revenue** and **Profit**\n", encoding="utf-8")
+
+        result = _list_uploaded_files_impl(include_outline=True, runtime=_runtime(), _paths=_paths(tmp_path))
+
+        assert result["files"][0]["outline"] == [{"title": "**Revenue** and **Profit**", "line": 1}]
+
     def test_no_runtime_returns_empty(self):
         result = _list_uploaded_files_impl(runtime=None)
         assert result["files"] == []