diff --git a/extra/release.py b/extra/release.py
index 75ba0b7b5..b8aa28f46 100755
--- a/extra/release.py
+++ b/extra/release.py
@@ -35,7 +35,8 @@ RST_REPLACEMENTS: list[Replacement] = [
 MD_REPLACEMENTS: list[Replacement] = [
     (r"^  (- )", r"\1"),  # remove indent from top-level bullet points
     (r"^ +(  - )", r"\1"),  # adjust nested bullet points indent
-    (r"^(\w[^\n]+):(?=\n\n[^ ])", r"### \1"),  # make sections headers
+    (r"^(\w[^\n]{,80}):(?=\n\n[^ ])", r"### \1"),  # format section headers
+    (r"^(\w[^\n]{81,}):(?=\n\n[^ ])", r"**\1**"),  # and bolden too long ones
     (r"^- `/?plugins/(\w+)`:?", r"- Plugin **`\1`**:"),  # highlight plugins
     (r"^- `(\w+)-cmd`:?", r"- Command **`\1`**:"),  # highlight commands
     (r"### [^\n]+\n+(?=### )", ""),  # remove empty sections
diff --git a/test/test_release.py b/test/test_release.py
index f69389d54..39b6b63fc 100644
--- a/test/test_release.py
+++ b/test/test_release.py
@@ -45,6 +45,9 @@ Bug fixes:
   * First
   * Second
 
+Section naaaaaaaaaaaaaaaaaaaaaaaammmmmmmmmmmmmmmmeeeeeeeeeeeeeee with over 80
+characters:
+
 Empty section:
 
 Other changes:
@@ -85,6 +88,8 @@ You can do something with this command:
   - First nested bullet point with some text that wraps to the next line
   - Second nested bullet point
 
+**Section naaaaaaaaaaaaaaaaaaaaaaaammmmmmmmmmmmmmmmeeeeeeeeeeeeeee with over 80 characters**
+
 ### 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)