diff --git a/Lib/test/test_threading.py b/Lib/test/test_threading.py
index 9e4972ecb640df..37c24dd5de8037 100644
--- a/Lib/test/test_threading.py
+++ b/Lib/test/test_threading.py
@@ -251,6 +251,14 @@ def f(mutex):
         #Issue 29376
         self.assertTrue(threading._active[tid].is_alive())
         self.assertRegex(repr(threading._active[tid]), '_DummyThread')
+
+        # Issue gh-106236:
+        with self.assertRaises(AssertionError):
+            threading._active[tid].join()
+        threading._active[tid]._started.clear()
+        with self.assertRaises(AssertionError):
+            threading._active[tid].is_alive()
+
         del threading._active[tid]
 
     # PyThreadState_SetAsyncExc() is a CPython-only gimmick, not (currently)
diff --git a/Lib/threading.py b/Lib/threading.py
index df273870fa4273..4565fe8d0a0eec 100644
--- a/Lib/threading.py
+++ b/Lib/threading.py
@@ -1451,11 +1451,12 @@ def _stop(self):
         pass
 
     def is_alive(self):
-        assert not self._is_stopped and self._started.is_set()
-        return True
+        if not self._is_stopped and self._started.is_set():
+            return True
+        raise AssertionError("thread is not alive")
 
     def join(self, timeout=None):
-        assert False, "cannot join a dummy thread"
+        raise AssertionError("cannot join a dummy thread")
 
 
 # Global API functions
diff --git a/Misc/NEWS.d/next/Library/2023-06-29-15-10-44.gh-issue-106236.EAIX4l.rst b/Misc/NEWS.d/next/Library/2023-06-29-15-10-44.gh-issue-106236.EAIX4l.rst
new file mode 100644
index 00000000000000..3c50df6e7ed680
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2023-06-29-15-10-44.gh-issue-106236.EAIX4l.rst
@@ -0,0 +1,3 @@
+Replace ``assert`` statements with ``raise AssertionError`` in
+:mod:`threading`, so the behaviour of ``_DummyThread`` with and without
+``-OO`` is consistent.