diff --git a/fe/fe-core/src/main/java/org/apache/doris/nereids/rules/rewrite/AdjustNullable.java b/fe/fe-core/src/main/java/org/apache/doris/nereids/rules/rewrite/AdjustNullable.java
index 43a757ec3282e0..8592d3f22a0294 100644
--- a/fe/fe-core/src/main/java/org/apache/doris/nereids/rules/rewrite/AdjustNullable.java
+++ b/fe/fe-core/src/main/java/org/apache/doris/nereids/rules/rewrite/AdjustNullable.java
@@ -34,6 +34,7 @@
 import org.apache.doris.nereids.trees.plans.logical.LogicalAggregate;
 import org.apache.doris.nereids.trees.plans.logical.LogicalApply;
 import org.apache.doris.nereids.trees.plans.logical.LogicalCTEConsumer;
+import org.apache.doris.nereids.trees.plans.logical.LogicalCatalogRelation;
 import org.apache.doris.nereids.trees.plans.logical.LogicalFilter;
 import org.apache.doris.nereids.trees.plans.logical.LogicalGenerate;
 import org.apache.doris.nereids.trees.plans.logical.LogicalJoin;
@@ -97,6 +98,25 @@ public Plan visit(Plan plan, Map<ExprId, Slot> replaceMap) {
         return logicalPlan;
     }
 
+    @Override
+    public Plan visitLogicalCatalogRelation(LogicalCatalogRelation relation, Map<ExprId, Slot> replaceMap) {
+        relation = (LogicalCatalogRelation) super.visit(relation, replaceMap);
+        relation = (LogicalCatalogRelation) relation.recomputeLogicalProperties();
+        for (Slot slot : relation.getOutput()) {
+            replaceMap.put(slot.getExprId(), slot);
+        }
+        Optional<List<NamedExpression>> newVirtualColumns
+                = updateExpressions(relation.getVirtualColumns(), replaceMap, true);
+        if (!newVirtualColumns.isPresent()) {
+            return relation;
+        }
+        for (NamedExpression newVirtualColumn : newVirtualColumns.get()) {
+            replaceMap.put(newVirtualColumn.getExprId(), newVirtualColumn.toSlot());
+        }
+        return relation.withVirtualColumns(newVirtualColumns.get())
+                .recomputeLogicalProperties();
+    }
+
     @Override
     public Plan visitLogicalSink(LogicalSink<? extends Plan> logicalSink, Map<ExprId, Slot> replaceMap) {
         logicalSink = (LogicalSink<? extends Plan>) super.visit(logicalSink, replaceMap);
diff --git a/regression-test/data/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.out b/regression-test/data/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.out
new file mode 100644
index 00000000000000..ea65f366267586
--- /dev/null
+++ b/regression-test/data/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.out
@@ -0,0 +1,17 @@
+-- This file is automatically generated. You should know what you did if you want to edit this
+-- !left_join_shape --
+PhysicalResultSink
+--hashJoin[INNER_JOIN] hashCondition=((t1.c_int = t2.c_int)) otherCondition=() build RFs:RF0 c_int->[c_int];RF1 c_int->[c_int]
+----PhysicalOlapScan[tbl_adjust_virtual_slot_nullable_1] apply RFs: RF0 RF1
+----PhysicalProject
+------filter(OR[( not dayofmonth(c_date) IN (1, 3)),( not dayofmonth(c_date) IN (2, 3))])
+--------PhysicalOlapScan[tbl_adjust_virtual_slot_nullable_2]
+
+-- !left_join_result --
+1	2020-01-01	1	2022-02-01
+1	2020-01-01	1	2022-02-02
+1	2020-01-02	1	2022-02-01
+1	2020-01-02	1	2022-02-02
+1	2020-01-03	1	2022-02-01
+1	2020-01-03	1	2022-02-02
+
diff --git a/regression-test/suites/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.groovy b/regression-test/suites/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.groovy
new file mode 100644
index 00000000000000..80d4b9fd5bef15
--- /dev/null
+++ b/regression-test/suites/query_p0/virtual_slot_ref/adjust_virtual_slot_nullable.groovy
@@ -0,0 +1,60 @@
+// Licensed to the Apache Software Foundation (ASF) under one
+// or more contributor license agreements.  See the NOTICE file
+// distributed with this work for additional information
+// regarding copyright ownership.  The ASF licenses this file
+// to you under the Apache License, Version 2.0 (the
+// "License"); you may not use this file except in compliance
+// with the License.  You may obtain a copy of the License at
+//
+//   http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing,
+// software distributed under the License is distributed on an
+// "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+// KIND, either express or implied.  See the License for the
+// specific language governing permissions and limitations
+// under the License.
+
+suite("adjust_virtual_slot_nullable") {
+    def tbl1 = "tbl_adjust_virtual_slot_nullable_1"
+    def tbl2 = "tbl_adjust_virtual_slot_nullable_2"
+    multi_sql """
+        SET ignore_shape_nodes='PhysicalDistribute';
+        drop table if exists ${tbl1} force;
+        drop table if exists ${tbl2} force;
+        create table ${tbl1} (c_int int not null, c_date date not null) properties('replication_num' = '1');
+        create table ${tbl2} (c_int int not null, c_date date not null) properties('replication_num' = '1');
+        insert into ${tbl1} values
+            (1, '2020-01-01'),
+            (1, '2020-01-02'),
+            (1, '2020-01-03'),
+            (2, '2021-01-01'),
+            (2, '2021-01-02'),
+            (2, '2021-01-03');
+        insert into ${tbl2} values
+            (1, '2022-02-01'),
+            (1, '2022-02-02'),
+            (1, '2022-02-03');
+    """
+
+    def querySql = """
+        SELECT t1.*, t2.*
+        FROM
+            ${tbl1} AS t1
+        LEFT JOIN ${tbl2} AS t2
+        ON  t1.c_int = t2.c_int
+        WHERE
+            NOT (
+                    day(t2.c_date) IN (1, 3)
+                AND
+                    day(t2.c_date) IN (2, 3, 3)
+                );
+    """
+
+    explainAndOrderResult 'left_join', querySql
+    explain {
+        sql querySql
+        verbose true
+        contains 'type=tinyint, nullable=false, isAutoIncrement=false, subColPath=null, virtualColumn=dayofmonth(c_date'
+    }
+}