diff --git a/tests/pytest/util/tserror.py b/tests/pytest/util/tserror.py
index d930c82b1d..0d88d78e80 100644
--- a/tests/pytest/util/tserror.py
+++ b/tests/pytest/util/tserror.py
@@ -7,9 +7,11 @@ TAOS_DEF_ERROR_CODE = ctypes.c_int32(0x80000000).value
 TSDB_CODE_MND_FUNC_NOT_EXIST    = (TAOS_DEF_ERROR_CODE | 0x0374)
 
 
+TSDB_CODE_TSC_INVALID_OPERATION = (TAOS_DEF_ERROR_CODE | 0x0200)
+
 TSDB_CODE_UDF_FUNC_EXEC_FAILURE = (TAOS_DEF_ERROR_CODE | 0x290A)
 
 
 TSDB_CODE_TSC_INTERNAL_ERROR = (TAOS_DEF_ERROR_CODE | 0x02FF)
 
-TSDB_CODE_TSC_INVALID_OPERATION = (TAOS_DEF_ERROR_CODE | 0x0200)
+TSDB_CODE_PAR_SYNTAX_ERROR = (TAOS_DEF_ERROR_CODE | 0x2600)
diff --git a/tests/system-test/2-query/join.py b/tests/system-test/2-query/join.py
index 5d5020ab4b..34f2d0ecb2 100644
--- a/tests/system-test/2-query/join.py
+++ b/tests/system-test/2-query/join.py
@@ -356,6 +356,11 @@ class TDTestCase:
     def join_semantic_test(self, dbname=DBNAME):
         tdSql.query("select ct1.c_int from db.ct1 as ct1 join db1.ct1 as cy1 on ct1.ts=cy1.ts")
         tdSql.checkRows(self.rows)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 semi join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 anti join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 outer join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 asof join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 window join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
         
         tdSql.query("select ct1.c_int from db.ct1 as ct1 join db1.ct1 as cy1 on ct1.ts=cy1.ts")
         tdSql.checkRows(self.rows)
@@ -390,6 +395,9 @@ class TDTestCase:
         
         tdSql.query("select ct1.c_int from db.ct1 as ct1 full join db1.ct1 as cy1 on ct1.ts=cy1.ts join db1.ct1 as cy2 on ct1.ts=cy2.ts")
         tdSql.checkRows(self.rows)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 full semi join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 full anti join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.query("select ct1.c_int from db.ct1 as ct1 full outer join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
         tdSql.query("select * from db.ct1 join db.ct2 join db.ct3 on ct2.ts=ct3.ts on ct1.ts=ct2.ts")
         tdSql.checkRows(0)
         tdSql.execute(f'create table db.ct1_2 using db.stb1 tags ( 102 )')
@@ -398,6 +406,13 @@ class TDTestCase:
         tdSql.execute(f'insert into db.ct1_3 (select * from db.ct1)')
         tdSql.query("select * from db.ct1 join db.ct1_2 join db.ct1_3 on ct1_2.ts=ct1_3.ts on ct1.ts=ct1_2.ts")
         tdSql.checkRows(self.rows)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 full asof join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        tdSql.error("select ct1.c_int from db.ct1 as ct1 full window join db1.ct1 as cy1 on ct1.ts=cy1.ts", TSDB_CODE_PAR_SYNTAX_ERROR)
+        
+        tdSql.query("select ct1.c_int from db.ct1 as ct1 left join db1.ct1 as cy1 on ct1.ts=cy1.ts")
+        tdSql.checkRows(self.rows)
+        tdSql.query("select ct1.c_int from db.ct1 as ct1 right join db1.ct1 as cy1 on ct1.ts=cy1.ts")
+        tdSql.checkRows(self.rows)
         
         tdSql.execute("drop table db.ct1_2")
         tdSql.execute("drop table db.ct1_3")
diff --git a/tests/system-test/2-query/last_row.py b/tests/system-test/2-query/last_row.py
index dd510459b6..40d752e40e 100644
--- a/tests/system-test/2-query/last_row.py
+++ b/tests/system-test/2-query/last_row.py
@@ -969,6 +969,11 @@ class TDTestCase:
         tdSql.checkData(0, 0, 6)
         tdSql.checkData(0, 1, 1734574929004)
         tdSql.checkData(0, 2, 4)
+        tdSql.query(f'select count(1), last_row(ts), last_row(c0) from (select * from (select * from {dbname}.meters))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 6)
+        tdSql.checkData(0, 1, 1734574929004)
+        tdSql.checkData(0, 2, 4)
         tdSql.query(f'select tbname, last_row(ts), last_row(c0) from (select *, tbname from {dbname}.meters) group by tbname order by tbname')
         tdSql.checkRows(2)
         tdSql.checkData(0, 0, 'd0')
@@ -977,6 +982,14 @@ class TDTestCase:
         tdSql.checkData(1, 0, 'd1')
         tdSql.checkData(1, 1, 1734574929000)
         tdSql.checkData(1, 2, 1)
+        tdSql.query(f'select tbname, last_row(ts), last_row(c0) from (select * from  (select *, tbname from {dbname}.meters)) group by tbname order by tbname')
+        tdSql.checkRows(2)
+        tdSql.checkData(0, 0, 'd0')
+        tdSql.checkData(0, 1, 1734574929004)
+        tdSql.checkData(0, 2, 4)
+        tdSql.checkData(1, 0, 'd1')
+        tdSql.checkData(1, 1, 1734574929000)
+        tdSql.checkData(1, 2, 1)
         tdSql.query(f'select count(1), last_row(ts), last_row(c0) from (select * from {dbname}.d0)')
         tdSql.checkRows(1)
         tdSql.checkData(0, 0, 5)
@@ -988,6 +1001,43 @@ class TDTestCase:
         tdSql.checkData(0, 1, 1734574929004)
         tdSql.checkData(0, 2, 4)
         
+        tdSql.execute(f'insert into {dbname}.d0 values(1734574930000, 1, 1, "c2", true)')
+        tdSql.execute(f'insert into {dbname}.d0 values(1734574931000, 1, 1, "c2", true)')
+        tdSql.execute(f'insert into {dbname}.d0 values(1734574932000, 1, 1, "c2", true)')
+        tdSql.query(f'select last_row(_wstart) from (select _wstart, _wend, count(1) from {dbname}.meters interval(1s))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.query(f'select last_row(_wstart), count(1) from (select _wstart, _wend, count(1) from {dbname}.meters interval(1s))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.checkData(0, 1, 4)
+        tdSql.query(f'select last_row(_wstart) from (select _wstart, _wend, count(1) from {dbname}.meters partition by tbname interval(1s))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.query(f'select last_row(_wstart), count(1) from (select _wstart, _wend, count(1) from {dbname}.meters  partition by tbname interval(1s))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.checkData(0, 1, 5)
+        tdSql.query(f'select first(_wstart), count(1) from (select _wstart, _wend, count(1) from {dbname}.meters interval(1s))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574929000)
+        tdSql.checkData(0, 1, 4)
+        
+        tdSql.query(f'select last_row(_wstart) from (select * from (select _wstart, _wend, count(1) from {dbname}.meters interval(1s)))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.query(f'select last_row(_wstart), count(1) from (select * from (select _wstart, _wend, count(1) from {dbname}.meters interval(1s)))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.checkData(0, 1, 4)
+        tdSql.query(f'select last_row(_wstart) from (select * from (select _wstart, _wend, count(1) from {dbname}.meters partition by tbname interval(1s)))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.query(f'select last_row(_wstart), count(1) from (select * from (select _wstart, _wend, count(1) from {dbname}.meters  partition by tbname interval(1s)))')
+        tdSql.checkRows(1)
+        tdSql.checkData(0, 0, 1734574932000)
+        tdSql.checkData(0, 1, 5)  
+        
     def run(self):  # sourcery skip: extract-duplicate-method, remove-redundant-fstring
         # tdSql.prepare()
 
@@ -1023,7 +1073,6 @@ class TDTestCase:
         
         self.lastrow_in_subquery("db1")
 
-
     def stop(self):
         tdSql.close()
         tdLog.success(f"{__file__} successfully executed")