diff --git a/extra/release.py b/extra/release.py
index 89c6fa72d..5a4baf423 100755
--- a/extra/release.py
+++ b/extra/release.py
@@ -7,6 +7,7 @@ from __future__ import annotations
 import re
 import subprocess
 from datetime import datetime, timezone
+from functools import partial
 from pathlib import Path
 from typing import Callable
 
@@ -19,7 +20,6 @@ BASE = Path(__file__).parent.parent.absolute()
 PYPROJECT = BASE / "pyproject.toml"
 CHANGELOG = BASE / "docs" / "changelog.rst"
 
-MD_CHANGELOG_SECTION_LIST = re.compile(r"- .+?(?=\n\n###|$)", re.DOTALL)
 version_header = r"\d+\.\d+\.\d+ \([^)]+\)"
 RST_LATEST_CHANGES = re.compile(
     rf"{version_header}\n--+\s+(.+?)\n\n+{version_header}", re.DOTALL
@@ -37,6 +37,10 @@ MD_REPLACEMENTS: list[Replacement] = [
     (r"^- `(\w+)-cmd`:?", r"- Command **`\1`**:"),  # highlight commands
     (r"### [^\n]+\n+(?=### )", ""),  # remove empty sections
 ]
+order_bullet_points = partial(
+    re.compile("(\n- .*?(?=\n(?! *- )|$))", flags=re.DOTALL).sub,
+    lambda m: "\n- ".join(sorted(m.group().split("\n- "))),
+)
 
 
 def update_docs_config(text: str, new: Version) -> str:
@@ -136,10 +140,9 @@ def changelog_as_markdown(rst: str) -> str:
     for pattern, repl in MD_REPLACEMENTS:
         md = re.sub(pattern, repl, md, flags=re.M)
 
-    # sort list items alphabetically for each of the sections
-    return MD_CHANGELOG_SECTION_LIST.sub(
-        lambda m: "\n".join(sorted(m.group().splitlines())), md
-    )
+    # order bullet points in each of the lists alphabetically to
+    # improve readability
+    return order_bullet_points(md)
 
 
 @click.group()
diff --git a/test/test_release.py b/test/test_release.py
index 2e4633409..a206b4e76 100644
--- a/test/test_release.py
+++ b/test/test_release.py
@@ -63,9 +63,9 @@ def md_changelog():
 
 ### Other changes
 
+- Changed `bitesize` label to `good first issue`. Our [contribute](https://github.com/beetbox/beets/contribute) page is now automatically populated with these issues. :bug: (\#4855)
 
 # 2.1.0 (November 22, 2024)
-- Changed `bitesize` label to `good first issue`. Our [contribute](https://github.com/beetbox/beets/contribute) page is now automatically populated with these issues. :bug: (\#4855)
 
 ### Bug fixes