diff --git a/Misc/NEWS.d/next/Core and Builtins/2023-08-26-04-31-01.gh-issue-108487.1Gbr9k.rst b/Misc/NEWS.d/next/Core and Builtins/2023-08-26-04-31-01.gh-issue-108487.1Gbr9k.rst
new file mode 100644
index 00000000000000..277b7c067e2528
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2023-08-26-04-31-01.gh-issue-108487.1Gbr9k.rst	
@@ -0,0 +1 @@
+Move an assert that would cause a spurious crash in a devious case that should only trigger deoptimization.
diff --git a/Python/bytecodes.c b/Python/bytecodes.c
index a5cb117c7631c6..27d6dc1f90ee01 100644
--- a/Python/bytecodes.c
+++ b/Python/bytecodes.c
@@ -3344,9 +3344,9 @@ dummy_func(
         inst(CALL_NO_KW_LIST_APPEND, (unused/1, unused/2, callable, self, args[oparg] -- unused)) {
             ASSERT_KWNAMES_IS_NULL();
             assert(oparg == 1);
-            assert(self != NULL);
             PyInterpreterState *interp = tstate->interp;
             DEOPT_IF(callable != interp->callable_cache.list_append, CALL);
+            assert(self != NULL);
             DEOPT_IF(!PyList_Check(self), CALL);
             STAT_INC(CALL, hit);
             if (_PyList_AppendTakeRef((PyListObject *)self, args[0]) < 0) {
diff --git a/Python/generated_cases.c.h b/Python/generated_cases.c.h
index 4aa16f8311a2a0..38962e8347702a 100644
--- a/Python/generated_cases.c.h
+++ b/Python/generated_cases.c.h
@@ -4410,9 +4410,9 @@
             callable = stack_pointer[-2 - oparg];
             ASSERT_KWNAMES_IS_NULL();
             assert(oparg == 1);
-            assert(self != NULL);
             PyInterpreterState *interp = tstate->interp;
             DEOPT_IF(callable != interp->callable_cache.list_append, CALL);
+            assert(self != NULL);
             DEOPT_IF(!PyList_Check(self), CALL);
             STAT_INC(CALL, hit);
             if (_PyList_AppendTakeRef((PyListObject *)self, args[0]) < 0) {