diff --git a/Python/ast_opt.c b/Python/ast_opt.c
index d7a26e64150e55..2ccae3bfafb142 100644
--- a/Python/ast_opt.c
+++ b/Python/ast_opt.c
@@ -624,8 +624,10 @@ static int
 fold_compare(expr_ty node, PyArena *arena, _PyASTOptimizeState *state)
 {
     asdl_int_seq *ops;
-    asdl_expr_seq *args;
+    asdl_expr_seq *args, *elts;
+    expr_ty arg;
     Py_ssize_t i;
+    Py_ssize_t elts_len;
 
     ops = node->v.Compare.ops;
     args = node->v.Compare.comparators;
@@ -633,11 +635,79 @@ fold_compare(expr_ty node, PyArena *arena, _PyASTOptimizeState *state)
        tuple or frozenset respectively. */
     i = asdl_seq_LEN(ops) - 1;
     int op = asdl_seq_GET(ops, i);
+    arg = asdl_seq_GET(args, i);
+    _Bool is_lhs_constant = (node->v.Compare.left->kind) == Constant_kind;
+
     if (op == In || op == NotIn) {
-        if (!fold_iter((expr_ty)asdl_seq_GET(args, i), arena, state)) {
-            return 0;
+        if ((arg->kind) == List_kind) {
+            asdl_expr_seq *list_elts = arg->v.List.elts;
+            if (has_starred(list_elts))
+                return 1;
+            expr_context_ty ctx = arg->v.List.ctx;
+            arg->kind = Tuple_kind;
+            arg->v.Tuple.elts = list_elts;
+            arg->v.Tuple.ctx = ctx;
+            elts = list_elts;
+        }
+        else if ((arg->kind) == Dict_kind) {
+            elts = arg->v.Dict.keys;
+            arg->kind = Set_kind;
+            arg->v.Set.elts = elts;
+        }
+        else if ((arg->kind) == Set_kind) {
+            elts = arg->v.Set.elts;
+        }
+        else {
+            return 1;
+        }
+
+        elts_len = asdl_seq_LEN(elts);
+        if (!elts_len) {
+            return make_const(node, op == In ? Py_False : Py_True, arena);
+        }
+
+        PyObject *newval = PyTuple_New(elts_len);
+        if (newval == NULL) {
+            PyErr_Clear();
+            return 1;
         }
+
+        for (Py_ssize_t j = 0; j < elts_len; j++) {
+            expr_ty e = (expr_ty)asdl_seq_GET(elts, j);
+            if (e->kind != Constant_kind) {
+                Py_DECREF(newval);
+                return 1;
+            }
+            PyObject *v = e->v.Constant.value;
+            PyTuple_SET_ITEM(newval, j, Py_NewRef(v));
+            if (is_lhs_constant &&
+                (v == (node->v.Compare.left->v.Constant.value)))
+            {
+                Py_DECREF(newval);
+                return make_const(node, op == In ? Py_True : Py_False, arena);
+            }
+        }
+
+        if ((arg->kind) == Set_kind) {
+            PyObject *frozenset = PyFrozenSet_New(newval);
+            if (frozenset == NULL) {
+                PyErr_Clear();
+                Py_DECREF(newval);
+                return 1;
+            }
+            Py_SETREF(newval, frozenset);
+            return make_const(arg, frozenset, arena);
+        }
+        return make_const(arg, newval, arena);
     }
+    else if (((op == Eq) || (op == NotEq)) &&
+             ((arg->kind) == Constant_kind) &&
+             is_lhs_constant)
+    {
+        if (((node->v.Compare.left)->v.Constant.value) == (arg->v.Constant.value))
+            return make_const(node, op == Eq ? Py_True : Py_False, arena);
+    }
+
     return 1;
 }