diff --git a/expression/integration_test.go b/expression/integration_test.go
index b74c7334c8bf6..d739c81c433d0 100755
--- a/expression/integration_test.go
+++ b/expression/integration_test.go
@@ -6184,6 +6184,17 @@ func (s *testIntegrationSuite) TestIssue15992(c *C) {
 	tk.MustExec("drop table t0;")
 }
 
+func (s *testIntegrationSuite) TestIssue16419(c *C) {
+	tk := testkit.NewTestKitWithInit(c, s.store)
+	tk.MustExec("use test;")
+	tk.MustExec("drop table if exists t0")
+	tk.MustExec("drop table if exists t1")
+	tk.MustExec("CREATE TABLE t0(c0 INT);")
+	tk.MustExec("CREATE TABLE t1(c0 INT);")
+	tk.MustQuery("SELECT * FROM t1 NATURAL LEFT JOIN t0 WHERE NOT t1.c0;").Check(testkit.Rows())
+	tk.MustExec("drop table t0, t1;")
+}
+
 func (s *testIntegrationSuite) TestIssue16029(c *C) {
 	tk := testkit.NewTestKit(c, s.store)
 	tk.MustExec("use test;")
diff --git a/planner/core/rule_predicate_push_down.go b/planner/core/rule_predicate_push_down.go
index 812a373c7889b..0d1951ab35521 100644
--- a/planner/core/rule_predicate_push_down.go
+++ b/planner/core/rule_predicate_push_down.go
@@ -337,7 +337,7 @@ func simplifyOuterJoin(p *LogicalJoin, predicates []expression.Expression) {
 // If it is a conjunction containing a null-rejected condition as a conjunct.
 // If it is a disjunction of null-rejected conditions.
 func isNullRejected(ctx sessionctx.Context, schema *expression.Schema, expr expression.Expression) bool {
-	expr = expression.PushDownNot(nil, expr)
+	expr = expression.PushDownNot(ctx, expr)
 	sc := ctx.GetSessionVars().StmtCtx
 	sc.InNullRejectCheck = true
 	result := expression.EvaluateExprWithNull(ctx, schema, expr)