diff --git a/Misc/NEWS.d/next/Build/2022-05-25-21-23-37.gh-issue-92886.i5gbQo.rst b/Misc/NEWS.d/next/Build/2022-05-25-21-23-37.gh-issue-92886.i5gbQo.rst
new file mode 100644
index 00000000000000..bdf70f6ea532cf
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2022-05-25-21-23-37.gh-issue-92886.i5gbQo.rst
@@ -0,0 +1 @@
+Remove assert in :func:`clinic.permute_optional_groups` so that it works as intended, and tests pass, when running with optimizations (``-O``).
diff --git a/Misc/NEWS.d/next/Build/2022-05-25-22-09-19.gh-issue-92886.i5gbQo.rst b/Misc/NEWS.d/next/Build/2022-05-25-22-09-19.gh-issue-92886.i5gbQo.rst
new file mode 100644
index 00000000000000..bdf70f6ea532cf
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2022-05-25-22-09-19.gh-issue-92886.i5gbQo.rst
@@ -0,0 +1 @@
+Remove assert in :func:`clinic.permute_optional_groups` so that it works as intended, and tests pass, when running with optimizations (``-O``).
diff --git a/Tools/clinic/clinic.py b/Tools/clinic/clinic.py
index 53e29df8a8e40f..da4371193cf470 100755
--- a/Tools/clinic/clinic.py
+++ b/Tools/clinic/clinic.py
@@ -495,8 +495,8 @@ def permute_optional_groups(left, required, right):
     required = tuple(required)
     result = []
 
-    if not required:
-        assert not left
+    if not required and left:
+        raise AssertionError('If required is empty, left must also be empty.')
 
     accumulator = []
     counts = set()