diff --git a/src/pkgmgr/actions/release/files/changelog_lint.py b/src/pkgmgr/actions/release/files/changelog_lint.py
index 5a78b9e..b9226a9 100644
--- a/src/pkgmgr/actions/release/files/changelog_lint.py
+++ b/src/pkgmgr/actions/release/files/changelog_lint.py
@@ -7,10 +7,11 @@ import shutil
 import subprocess
 import tempfile
 
-_HEADING = re.compile(r"^\s*#{1,6}\s+(.*?)\s*#*\s*$")
+_HEADING = re.compile(r"^\s*(#{1,6})\s+(.*?)\s*#*\s*$")
 _INLINE_CODE = re.compile(r"`([^`\n]+)`")
 _FINDING = re.compile(r"\bMD\d{3}\b")
 _MULTI_BLANK = re.compile(r"\n{3,}")
+_ENTRY_LEVEL = 3
 
 
 class ChangelogLintError(RuntimeError):
@@ -20,10 +21,10 @@ class ChangelogLintError(RuntimeError):
 def transform_changelog_message(text: str) -> str:
     """Normalise a free-form release message into the changelog house style.
 
-    A leading ``#`` heading becomes a bold line of its own (markdown
-    headings inside an entry body would collide with the ``## [version]``
-    structure), and inline ``code`` spans become ``*italic*`` so the entry
-    stays free of backticks.
+    Headings are pushed below the ``## [version]`` line the entry is filed
+    under, so they nest instead of competing with it. Bolding them instead
+    would read as a heading to markdown-lint and fail MD036. Inline ``code``
+    spans become ``*italic*`` so the entry stays free of backticks.
     """
     text = _INLINE_CODE.sub(r"*\1*", text)
 
@@ -31,9 +32,10 @@ def transform_changelog_message(text: str) -> str:
     for line in text.split("\n"):
         heading = _HEADING.match(line)
         if heading:
+            level = max(len(heading.group(1)), _ENTRY_LEVEL)
             if out and out[-1].strip():
                 out.append("")
-            out.append(f"**{heading.group(1).strip()}**")
+            out.append(f"{'#' * level} {heading.group(2).strip()}")
             out.append("")
         else:
             out.append(line)
diff --git a/src/pkgmgr/actions/release/files/changelog_md.py b/src/pkgmgr/actions/release/files/changelog_md.py
index 0cc4e61..2243176 100644
--- a/src/pkgmgr/actions/release/files/changelog_md.py
+++ b/src/pkgmgr/actions/release/files/changelog_md.py
@@ -80,6 +80,12 @@ def update_changelog(
             print(f"  - {finding}")
         print()
 
+    def _wait_for_reader() -> None:
+        try:
+            input("[INFO] Press Enter to re-open the editor and fix the entry...")
+        except EOFError:
+            print("[INFO] Re-opening the editor so you can fix the entry...")
+
     if message is not None:
         body, entry = _entry_for(message)
         findings = lint_changelog_entry(changelog_path, entry)
@@ -92,19 +98,21 @@ def update_changelog(
         body, entry = _entry_for(message or f"Release {new_version}")
     else:
         attempt: str | None = None
+        rejected: list[str] | None = None
         while True:
             print(
-                "\n[INFO] Provide the changelog entry — a leading '#' becomes "
-                "bold, `code` becomes italic.\n"
+                "\n[INFO] Provide the changelog entry - a leading '#' becomes "
+                "a sub-heading, `code` becomes italic.\n"
             )
-            raw = _open_editor_for_changelog(attempt)
+            raw = _open_editor_for_changelog(attempt, rejected)
             body, entry = _entry_for(raw or f"Release {new_version}")
             findings = lint_changelog_entry(changelog_path, entry)
             if not findings:
                 break
             _print_findings(findings)
             attempt = body
-            print("[INFO] Re-opening the editor so you can fix the entry...")
+            rejected = findings
+            _wait_for_reader()
 
     changelog = ""
     if os.path.exists(changelog_path):
diff --git a/src/pkgmgr/actions/release/files/editor.py b/src/pkgmgr/actions/release/files/editor.py
index d83aa12..0f29bbc 100644
--- a/src/pkgmgr/actions/release/files/editor.py
+++ b/src/pkgmgr/actions/release/files/editor.py
@@ -6,7 +6,14 @@ import subprocess
 import tempfile
 
 
-def _open_editor_for_changelog(initial_message: str | None = None) -> str:
+def _open_editor_for_changelog(
+    initial_message: str | None = None,
+    findings: list[str] | None = None,
+) -> str:
+    """Args:
+    initial_message: the previous attempt, pre-loaded for editing.
+    findings: why that attempt was rejected, shown above it.
+    """
     editor = os.environ.get("EDITOR", "nano")
 
     with tempfile.NamedTemporaryFile(
@@ -18,9 +25,15 @@ def _open_editor_for_changelog(initial_message: str | None = None) -> str:
         tmp.write(
             "; Write the changelog entry for this release.\n"
             "; Lines starting with ';' are ignored.\n"
-            "; A leading '#' becomes bold; `code` becomes italic.\n"
-            "; Empty result will fall back to a generic message.\n\n"
+            "; A leading '#' becomes a sub-heading; `code` becomes italic.\n"
+            "; Empty result will fall back to a generic message.\n"
         )
+        if findings:
+            tmp.write(";\n; markdown-lint rejected the previous entry:\n")
+            for finding in findings:
+                for line in str(finding).splitlines() or [""]:
+                    tmp.write(f";   {line}\n")
+        tmp.write("\n")
         if initial_message:
             tmp.write(initial_message.strip() + "\n")
         tmp.flush()
diff --git a/tests/unit/pkgmgr/actions/release/test_changelog_lint.py b/tests/unit/pkgmgr/actions/release/test_changelog_lint.py
index 6cf092b..109df0e 100644
--- a/tests/unit/pkgmgr/actions/release/test_changelog_lint.py
+++ b/tests/unit/pkgmgr/actions/release/test_changelog_lint.py
@@ -9,15 +9,16 @@ from pkgmgr.actions.release.files.changelog_lint import (
 
 
 class TestTransformChangelogMessage(unittest.TestCase):
-    def test_heading_becomes_bold(self) -> None:
+    def test_heading_is_pushed_below_the_release_heading(self) -> None:
         out = transform_changelog_message("# Title\n\nbody")
-        self.assertIn("**Title**", out)
-        self.assertNotIn("# Title", out)
+        self.assertIn("### Title", out)
+        self.assertNotIn("**Title**", out)
 
-    def test_multi_hash_heading_becomes_bold(self) -> None:
-        self.assertEqual(
-            transform_changelog_message("### Sub heading"), "**Sub heading**"
-        )
+    def test_a_heading_already_deep_enough_keeps_its_level(self) -> None:
+        self.assertEqual(transform_changelog_message("### Sub heading"), "### Sub heading")
+
+    def test_a_deeper_heading_is_left_alone(self) -> None:
+        self.assertEqual(transform_changelog_message("#### Deeper"), "#### Deeper")
 
     def test_inline_code_becomes_italic(self) -> None:
         out = transform_changelog_message("use `pkgmgr release` now")
@@ -27,11 +28,12 @@ class TestTransformChangelogMessage(unittest.TestCase):
     def test_plain_message_is_unchanged(self) -> None:
         self.assertEqual(transform_changelog_message("just text"), "just text")
 
-    def test_no_heading_or_backtick_survives(self) -> None:
+    def test_no_backtick_survives_and_no_heading_competes(self) -> None:
         out = transform_changelog_message("# Heading\n\n* item with `code`")
         self.assertNotIn("`", out)
         for line in out.split("\n"):
-            self.assertFalse(line.lstrip().startswith("#"))
+            if line.lstrip().startswith("#"):
+                self.assertTrue(line.startswith("###"), line)
 
 
 class TestLintChangelogEntry(unittest.TestCase):
@@ -39,6 +41,13 @@ class TestLintChangelogEntry(unittest.TestCase):
         entry = "## [1.0.0] - 2026-01-01\n\n* a clean bullet\n\n"
         self.assertEqual(lint_changelog_entry("CHANGELOG.md", entry), [])
 
+    def test_a_structured_message_survives_its_own_transform(self) -> None:
+        body = transform_changelog_message(
+            "# Security\n\n* a bullet\n\n## Fixed\n\n* another bullet"
+        )
+        entry = f"## [1.0.0] - 2026-01-01\n\n{body}\n\n"
+        self.assertEqual(lint_changelog_entry("CHANGELOG.md", entry), [])
+
 
 if __name__ == "__main__":  # pragma: no cover
     unittest.main()
diff --git a/tests/unit/pkgmgr/actions/release/test_editor.py b/tests/unit/pkgmgr/actions/release/test_editor.py
new file mode 100644
index 0000000..fad9324
--- /dev/null
+++ b/tests/unit/pkgmgr/actions/release/test_editor.py
@@ -0,0 +1,60 @@
+from __future__ import annotations
+
+import unittest
+from unittest import mock
+
+from pkgmgr.actions.release.files.editor import _open_editor_for_changelog
+
+
+class TestOpenEditorForChangelog(unittest.TestCase):
+    def _buffer(self, **kwargs: object) -> str:
+        """Returns: what the editor was handed, with the editor itself a no-op."""
+        seen: dict[str, str] = {}
+
+        def record(argv: list[str]) -> int:
+            with open(argv[1], encoding="utf-8") as handle:
+                seen["text"] = handle.read()
+            return 0
+
+        with mock.patch(
+            "pkgmgr.actions.release.files.editor.subprocess.call", side_effect=record
+        ):
+            _open_editor_for_changelog(**kwargs)
+        return seen["text"]
+
+    def test_the_rejection_reaches_the_editor_the_entry_is_fixed_in(self) -> None:
+        text = self._buffer(
+            initial_message="### Security\n\n- a bullet",
+            findings=["changelog entry:3 error MD036/no-emphasis-as-heading"],
+        )
+        self.assertIn("MD036/no-emphasis-as-heading", text)
+        self.assertIn("### Security", text)
+
+    def test_every_finding_line_is_commented_out(self) -> None:
+        text = self._buffer(findings=["first line\nsecond line"])
+        for line in text.splitlines():
+            if "line" in line and "ignored" not in line:
+                self.assertTrue(line.startswith(";"), line)
+
+    def test_a_finding_never_lands_in_the_entry(self) -> None:
+        seen: dict[str, str] = {}
+
+        def rewrite(argv: list[str]) -> int:
+            with open(argv[1], encoding="utf-8") as handle:
+                seen["text"] = handle.read()
+            return 0
+
+        with mock.patch(
+            "pkgmgr.actions.release.files.editor.subprocess.call", side_effect=rewrite
+        ):
+            kept = _open_editor_for_changelog(
+                initial_message="- a bullet", findings=["MD036 somewhere"]
+            )
+        self.assertEqual(kept, "- a bullet")
+
+    def test_without_findings_the_header_stays_as_it_was(self) -> None:
+        self.assertNotIn("markdown-lint rejected", self._buffer())
+
+
+if __name__ == "__main__":  # pragma: no cover
+    unittest.main()
diff --git a/tests/unit/pkgmgr/actions/release/test_files.py b/tests/unit/pkgmgr/actions/release/test_files.py
index 328725b..e65662a 100644
--- a/tests/unit/pkgmgr/actions/release/test_files.py
+++ b/tests/unit/pkgmgr/actions/release/test_files.py
@@ -334,9 +334,10 @@ class TestUpdateChangelog(unittest.TestCase):
             with open(path, encoding="utf-8") as f:
                 content = f.read()
 
-        self.assertIn("**Summary**", content)
+        self.assertIn("### Summary", content)
         self.assertIn("*foo*", content)
-        self.assertNotIn("# Summary", content)
+        self.assertNotIn("\n# Summary", content)
+        self.assertNotIn("\n## Summary", content)
         self.assertNotIn("`foo`", content)
 
     def test_update_changelog_preview_does_not_write(self) -> None: