fix(release/changelog): insert new entry under H1 instead of above it

update_changelog used to blindly prepend the new ## [version] entry to
the entire file body. When CHANGELOG.md leads with a # Changelog H1
the result was:

  ## [new] - YYYY-MM-DD
  ...
  # Changelog
  ## [old] - ...

which trips markdownlint MD041 (first-line-h1) and MD012
(no-multiple-blanks), and reads as if the document were two stacked
changelogs.

The new _insert_after_h1 helper:

* Synthesises # Changelog when the file is empty.
* Inserts the entry between the existing H1 (plus any intro prose)
  and the first existing ## release entry.
* For legacy headerless files (file starts with ##) prepends the
  synthesised H1 + entry, so the resulting document is also
  MD041-clean.

Tests cover the three layouts (empty, H1+existing-entries,
legacy-headerless). All 61 release-unit tests stay green.

Co-Authored-By: Claude Opus 4.7 <noreply@anthropic.com>

src/pkgmgr/actions/release/files/changelog_md.py

@@ -1,11 +1,50 @@
 from __future__ import annotations
 
 import os
+import re
 from datetime import date
 from typing import Optional
 
 from .editor import _open_editor_for_changelog
 
+H1_RE = re.compile(r"^#\s+\S", re.MULTILINE)
+H2_RE = re.compile(r"^##\s+\S", re.MULTILINE)
+
+
+def _insert_after_h1(existing: str, entry: str) -> str:
+    """Place *entry* after the H1 (and any intro prose), above the first H2.
+
+    If the file has no H1 we synthesise ``# Changelog`` so the resulting
+    document is markdown-lint-clean (MD041 first-line-h1).
+    If the file has no H2 yet we append *entry* after the H1 block.
+    Existing behaviour for legacy headerless files (file starts with
+    ``## ``) is preserved: *entry* is prepended unchanged.
+    """
+    if not existing.strip():
+        return f"# Changelog\n\n{entry}"
+
+    if not H1_RE.search(existing):
+        # Legacy layout: file starts with `## [version]` and has no H1.
+        # Synthesise the H1 so the merged file is lint-clean.
+        return f"# Changelog\n\n{entry}{existing.lstrip()}"
+
+    # File has an H1. Find the first H2 (existing release section).
+    h2_match = H2_RE.search(existing)
+    if h2_match is None:
+        # H1 + optional intro but no release entries yet — append entry
+        # after a single blank line.
+        suffix = (
+            ""
+            if existing.endswith("\n\n")
+            else ("\n" if existing.endswith("\n") else "\n\n")
+        )
+        return f"{existing}{suffix}{entry}"
+
+    # Insert new entry just before the first H2.
+    head = existing[: h2_match.start()].rstrip("\n") + "\n\n"
+    tail = existing[h2_match.start() :]
+    return f"{head}{entry}{tail}"
+
 
 def update_changelog(
     changelog_path: str,
@@ -13,9 +52,11 @@ def update_changelog(
     message: Optional[str] = None,
     preview: bool = False,
 ) -> str:
-    """
+    """Insert a new release entry into CHANGELOG.md.
-    Prepend a new release section to CHANGELOG.md with the new version,
+
-    current date, and a message.
+    The entry is placed after the documents H1 heading (creating one if
+    missing) and above any existing release entries, so the result stays
+    markdown-lint-clean (MD041 first-line-h1, MD012 no-multiple-blanks).
     """
     today = date.today().isoformat()
 
@@ -32,8 +73,7 @@ def update_changelog(
             else:
                 message = editor_message
 
-    header = f"## [{new_version}] - {today}\n"
+    entry = f"## [{new_version}] - {today}\n\n* {message}\n\n"
-    header += f"\n* {message}\n\n"
 
     if os.path.exists(changelog_path):
         try:
@@ -45,14 +85,14 @@ def update_changelog(
     else:
         changelog = ""
 
-    new_changelog = header + "\n" + changelog if changelog else header
+    new_changelog = _insert_after_h1(changelog, entry)
 
     print("\n================ CHANGELOG ENTRY ================")
-    print(header.rstrip())
+    print(entry.rstrip())
     print("=================================================\n")
 
     if preview:
-        print(f"[PREVIEW] Would prepend new entry for {new_version} to CHANGELOG.md")
+        print(f"[PREVIEW] Would insert new entry for {new_version} into CHANGELOG.md")
         return message
 
     with open(changelog_path, "w", encoding="utf-8") as f:

tests/unit/pkgmgr/actions/release/test_files.py

@@ -256,7 +256,7 @@ class TestUpdateSpecVersion(unittest.TestCase):
 
 
 class TestUpdateChangelog(unittest.TestCase):
-    def test_update_changelog_creates_file_if_missing(self) -> None:
+    def test_update_changelog_creates_file_with_h1_if_missing(self) -> None:
         with tempfile.TemporaryDirectory() as tmpdir:
             path = os.path.join(tmpdir, "CHANGELOG.md")
             self.assertFalse(os.path.exists(path))
@@ -267,10 +267,35 @@ class TestUpdateChangelog(unittest.TestCase):
             with open(path, "r", encoding="utf-8") as f:
                 content = f.read()
 
-        self.assertIn("## [1.2.3]", content)
+        # New file must lead with an H1 so markdownlint MD041 is happy.
+        self.assertTrue(content.startswith("# Changelog\n\n## [1.2.3]"))
         self.assertIn("First release", content)
 
-    def test_update_changelog_prepends_entry_to_existing_content(self) -> None:
+    def test_update_changelog_inserts_below_existing_h1(self) -> None:
+        with tempfile.TemporaryDirectory() as tmpdir:
+            path = os.path.join(tmpdir, "CHANGELOG.md")
+            existing = "# Changelog\n\n## [0.1.0] - 2024-01-01\n\n* Initial content\n"
+            with open(path, "w", encoding="utf-8") as f:
+                f.write(existing)
+
+            update_changelog(path, "1.0.0", message="Second release", preview=False)
+
+            with open(path, "r", encoding="utf-8") as f:
+                content = f.read()
+
+        # H1 still on top, new entry above the existing one.
+        self.assertTrue(content.startswith("# Changelog\n\n## [1.0.0]"))
+        # Exactly one H1.
+        self.assertEqual(
+            content.count("\n# Changelog\n") + content.startswith("# Changelog\n"), 1
+        )
+        # Old entry still present, after the new one.
+        self.assertLess(
+            content.index("## [1.0.0]"),
+            content.index("## [0.1.0]"),
+        )
+
+    def test_update_changelog_legacy_headerless_gets_h1_synthesized(self) -> None:
         with tempfile.TemporaryDirectory() as tmpdir:
             path = os.path.join(tmpdir, "CHANGELOG.md")
             with open(path, "w", encoding="utf-8") as f:
@@ -281,7 +306,8 @@ class TestUpdateChangelog(unittest.TestCase):
             with open(path, "r", encoding="utf-8") as f:
                 content = f.read()
 
-        self.assertTrue(content.startswith("## [1.0.0]"))
+        # An H1 is added so MD041 is satisfied even for legacy files.
+        self.assertTrue(content.startswith("# Changelog\n\n## [1.0.0]"))
         self.assertIn("## [0.1.0] - 2024-01-01", content)
 
     def test_update_changelog_preview_does_not_write(self) -> None: