diff --git a/go/test/endtoend/vtgate/queries/subquery/subquery_test.go b/go/test/endtoend/vtgate/queries/subquery/subquery_test.go
index 01cc7b2ee54..13dc5e480f1 100644
--- a/go/test/endtoend/vtgate/queries/subquery/subquery_test.go
+++ b/go/test/endtoend/vtgate/queries/subquery/subquery_test.go
@@ -19,12 +19,11 @@ package subquery
 import (
 	"testing"
 
-	"vitess.io/vitess/go/test/endtoend/utils"
-
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"vitess.io/vitess/go/test/endtoend/cluster"
+	"vitess.io/vitess/go/test/endtoend/utils"
 )
 
 func start(t *testing.T) (utils.MySQLCompare, func()) {
@@ -58,6 +57,28 @@ func TestSubqueriesHasValues(t *testing.T) {
 	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id1 FROM t1 WHERE id1 > 10) ORDER BY id2`, `[[INT64(1)] [INT64(2)] [INT64(3)] [INT64(4)] [INT64(5)] [INT64(6)]]`)
 }
 
+func TestNotINQueries(t *testing.T) {
+	utils.SkipIfBinaryIsBelowVersion(t, 19, "vtgate")
+
+	// Tests NOT IN where the RHS contains all rows, some rows and no rows
+	mcmp, closer := start(t)
+	defer closer()
+
+	mcmp.Exec("insert into t1(id1, id2) values (0,1),(1,2),(2,3),(3,4),(4,5),(5,6)")
+	// no matching rows
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id1 FROM t1 WHERE id1 > 10) ORDER BY id2`, `[[INT64(1)] [INT64(2)] [INT64(3)] [INT64(4)] [INT64(5)] [INT64(6)]]`)
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id2 FROM t1 WHERE id2 > 10) ORDER BY id2`, `[[INT64(1)] [INT64(2)] [INT64(3)] [INT64(4)] [INT64(5)] [INT64(6)]]`)
+
+	// some matching rows
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id1 FROM t1 WHERE id1 > 3) ORDER BY id2`, `[[INT64(1)] [INT64(2)] [INT64(3)] [INT64(4)]]`)
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id2 FROM t1 WHERE id2 > 3) ORDER BY id2`, `[[INT64(1)] [INT64(2)] [INT64(3)] [INT64(4)]]`)
+
+	// all rows matching
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id1 FROM t1) ORDER BY id2`, `[]`)
+	mcmp.AssertMatches(`SELECT id2 FROM t1 WHERE id1 NOT IN (SELECT id2 FROM t1) ORDER BY id2`, `[[INT64(1)]]`)
+
+}
+
 // Test only supported in >= v16.0.0
 func TestSubqueriesExists(t *testing.T) {
 	utils.SkipIfBinaryIsBelowVersion(t, 16, "vtgate")
diff --git a/go/vt/vtgate/planbuilder/operators/subquery.go b/go/vt/vtgate/planbuilder/operators/subquery.go
index 55fcba6cd3b..a8564052ffa 100644
--- a/go/vt/vtgate/planbuilder/operators/subquery.go
+++ b/go/vt/vtgate/planbuilder/operators/subquery.go
@@ -262,7 +262,10 @@ func (sq *SubQuery) settleFilter(ctx *plancontext.PlanningContext, outer ops.Ope
 		predicates = append(predicates, sqlparser.NewArgument(hasValuesArg()), rhsPred)
 		sq.SubqueryValueName = sq.ArgName
 	case opcode.PulloutNotIn:
-		predicates = append(predicates, sqlparser.NewNotExpr(sqlparser.NewArgument(hasValuesArg())), rhsPred)
+		predicates = append(predicates, &sqlparser.OrExpr{
+			Left:  sqlparser.NewNotExpr(sqlparser.NewArgument(hasValuesArg())),
+			Right: rhsPred,
+		})
 		sq.SubqueryValueName = sq.ArgName
 	case opcode.PulloutValue:
 		predicates = append(predicates, rhsPred)
diff --git a/go/vt/vtgate/planbuilder/testdata/filter_cases.json b/go/vt/vtgate/planbuilder/testdata/filter_cases.json
index 3af60651eea..7cf1e830447 100644
--- a/go/vt/vtgate/planbuilder/testdata/filter_cases.json
+++ b/go/vt/vtgate/planbuilder/testdata/filter_cases.json
@@ -1966,7 +1966,7 @@
               "Sharded": true
             },
             "FieldQuery": "select id from `user` where 1 != 1",
-            "Query": "select id from `user` where not :__sq_has_values and id not in ::__sq1",
+            "Query": "select id from `user` where not :__sq_has_values or id not in ::__sq1",
             "Table": "`user`"
           }
         ]
@@ -2503,7 +2503,7 @@
                   "Sharded": true
                 },
                 "FieldQuery": "select id from `user` where 1 != 1",
-                "Query": "select id from `user` where not :__sq_has_values and id not in ::__sq1 and :__sq_has_values1 and id in ::__vals",
+                "Query": "select id from `user` where (not :__sq_has_values or id not in ::__sq1) and :__sq_has_values1 and id in ::__vals",
                 "Table": "`user`",
                 "Values": [
                   "::__sq2"
@@ -2950,7 +2950,7 @@
               "Sharded": true
             },
             "FieldQuery": "select id from `user` where 1 != 1",
-            "Query": "select id from `user` where id = 5 and id in (select user_extra.col from user_extra where user_extra.user_id = 5) and not :__sq_has_values and id not in ::__sq1",
+            "Query": "select id from `user` where id = 5 and id in (select user_extra.col from user_extra where user_extra.user_id = 5) and (not :__sq_has_values or id not in ::__sq1)",
             "Table": "`user`",
             "Values": [
               "INT64(5)"
diff --git a/go/vt/vtgate/planbuilder/testdata/tpch_cases.json b/go/vt/vtgate/planbuilder/testdata/tpch_cases.json
index 947f9cc0f96..42508c40db4 100644
--- a/go/vt/vtgate/planbuilder/testdata/tpch_cases.json
+++ b/go/vt/vtgate/planbuilder/testdata/tpch_cases.json
@@ -1551,7 +1551,7 @@
                               "Sharded": true
                             },
                             "FieldQuery": "select ps_suppkey, weight_string(ps_suppkey), ps_partkey from partsupp where 1 != 1",
-                            "Query": "select ps_suppkey, weight_string(ps_suppkey), ps_partkey from partsupp where not :__sq_has_values and ps_suppkey not in ::__sq1",
+                            "Query": "select ps_suppkey, weight_string(ps_suppkey), ps_partkey from partsupp where not :__sq_has_values or ps_suppkey not in ::__sq1",
                             "Table": "partsupp"
                           }
                         ]