diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/planner/DruidSqlValidator.java b/sql/src/main/java/org/apache/druid/sql/calcite/planner/DruidSqlValidator.java
index 5a901c72296e..d7665604ecce 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/planner/DruidSqlValidator.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/planner/DruidSqlValidator.java
@@ -22,7 +22,12 @@
 import org.apache.calcite.adapter.java.JavaTypeFactory;
 import org.apache.calcite.prepare.BaseDruidSqlValidator;
 import org.apache.calcite.prepare.CalciteCatalogReader;
+import org.apache.calcite.sql.SqlCall;
+import org.apache.calcite.sql.SqlKind;
+import org.apache.calcite.sql.SqlNode;
 import org.apache.calcite.sql.SqlOperatorTable;
+import org.apache.calcite.sql.validate.SqlValidatorScope;
+import org.apache.druid.error.InvalidSqlInput;
 
 /**
  * Druid extended SQL validator. (At present, it doesn't actually
@@ -39,4 +44,23 @@ protected DruidSqlValidator(
   {
     super(opTab, catalogReader, typeFactory, validatorConfig);
   }
+
+  @Override
+  public void validateCall(SqlCall call, SqlValidatorScope scope)
+  {
+    if (call.getKind() == SqlKind.NULLS_FIRST) {
+      SqlNode op0 = call.getOperandList().get(0);
+      if (op0.getKind() == SqlKind.DESCENDING) {
+        throw InvalidSqlInput.exception("DESCENDING ordering with NULLS FIRST is not supported!");
+      }
+    }
+    if (call.getKind() == SqlKind.NULLS_LAST) {
+      SqlNode op0 = call.getOperandList().get(0);
+      if (op0.getKind() != SqlKind.DESCENDING) {
+        throw InvalidSqlInput.exception("ASCENDING ordering with NULLS LAST is not supported!");
+      }
+    }
+
+    super.validateCall(call, scope);
+  }
 }
diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/planner/convertlet/DruidConvertletTable.java b/sql/src/main/java/org/apache/druid/sql/calcite/planner/convertlet/DruidConvertletTable.java
index 59ad4ef24f05..eadd2e48268d 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/planner/convertlet/DruidConvertletTable.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/planner/convertlet/DruidConvertletTable.java
@@ -67,6 +67,9 @@ public class DruidConvertletTable implements SqlRexConvertletTable
                    .add(SqlStdOperatorTable.NULLIF)
                    .add(SqlStdOperatorTable.COALESCE)
                    .add(SqlLibraryOperators.NVL)
+                   .add(SqlStdOperatorTable.DESC)
+                   .add(SqlStdOperatorTable.NULLS_FIRST)
+                   .add(SqlStdOperatorTable.NULLS_LAST)
                    .build();
 
   private final Map<SqlOperator, SqlRexConvertlet> table;
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
index 08fdbc3bfaa0..6f09e6372732 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
@@ -137,6 +137,9 @@
 import java.util.Map;
 import java.util.stream.Collectors;
 
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertThrows;
+
 public class CalciteQueryTest extends BaseCalciteQueryTest
 {
   @Test
@@ -14247,4 +14250,24 @@ public void testLatestByOnStringColumnWithoutMaxBytesSpecified()
             new Object[] {"abc", defaultString, "def", defaultString, "def", defaultString}
         ));
   }
+
+  @Test
+  public void testUnSupportedNullsFirst()
+  {
+    DruidException e = assertThrows(DruidException.class, () -> testBuilder()
+        .queryContext(ImmutableMap.of(PlannerContext.CTX_ENABLE_WINDOW_FNS, true))
+        .sql("SELECT dim1,ROW_NUMBER() OVER (ORDER BY dim1 DESC NULLS FIRST) from druid.foo")
+        .run());
+    assertEquals("DESCENDING ordering with NULLS FIRST is not supported!", e.getMessage());
+  }
+
+  @Test
+  public void testUnSupportedNullsLast()
+  {
+    DruidException e = assertThrows(DruidException.class, () -> testBuilder()
+        .queryContext(ImmutableMap.of(PlannerContext.CTX_ENABLE_WINDOW_FNS, true))
+        .sql("SELECT dim1,ROW_NUMBER() OVER (ORDER BY dim1 NULLS LAST) from druid.foo")
+        .run());
+    assertEquals("ASCENDING ordering with NULLS LAST is not supported!", e.getMessage());
+  }
 }
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/DrillWindowQueryTest.java b/sql/src/test/java/org/apache/druid/sql/calcite/DrillWindowQueryTest.java
index 969b59b5037e..b068c55c8e59 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/DrillWindowQueryTest.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/DrillWindowQueryTest.java
@@ -450,7 +450,8 @@ private static Object parseLongValue(final String val)
     }
     try {
       LocalTime v = LocalTime.parse(val);
-      return v.getMillisOfDay();
+      Long l = (long) v.getMillisOfDay();
+      return l;
     }
     catch (Exception e) {
     }
@@ -4385,7 +4386,7 @@ public void test_nestedAggs_nstdWinView01()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("aggregates/winFnQry_63")
   @Test
   public void test_aggregates_winFnQry_63()
@@ -4393,7 +4394,7 @@ public void test_aggregates_winFnQry_63()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_83")
   @Test
   public void test_aggregates_winFnQry_83()
@@ -4401,7 +4402,7 @@ public void test_aggregates_winFnQry_83()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("frameclause/multipl_wnwds/mulwind_01")
   @Test
   public void test_frameclause_multipl_wnwds_mulwind_01()
@@ -4409,7 +4410,7 @@ public void test_frameclause_multipl_wnwds_mulwind_01()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("frameclause/multipl_wnwds/mulwind_06")
   @Test
   public void test_frameclause_multipl_wnwds_mulwind_06()
@@ -4417,7 +4418,7 @@ public void test_frameclause_multipl_wnwds_mulwind_06()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("frameclause/multipl_wnwds/mulwind_07")
   @Test
   public void test_frameclause_multipl_wnwds_mulwind_07()
@@ -4425,7 +4426,6 @@ public void test_frameclause_multipl_wnwds_mulwind_07()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lag_func/lag_Fn_108")
   @Test
   public void test_lag_func_lag_Fn_108()
@@ -4433,7 +4433,6 @@ public void test_lag_func_lag_Fn_108()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lag_func/lag_Fn_109")
   @Test
   public void test_lag_func_lag_Fn_109()
@@ -4441,7 +4440,6 @@ public void test_lag_func_lag_Fn_109()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lag_func/lag_Fn_69")
   @Test
   public void test_lag_func_lag_Fn_69()
@@ -4449,7 +4447,6 @@ public void test_lag_func_lag_Fn_69()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lead_func/lead_Fn_103")
   @Test
   public void test_lead_func_lead_Fn_103()
@@ -4457,7 +4454,6 @@ public void test_lead_func_lead_Fn_103()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lead_func/lead_Fn_104")
   @Test
   public void test_lead_func_lead_Fn_104()
@@ -4465,7 +4461,6 @@ public void test_lead_func_lead_Fn_104()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
   @DrillTest("lead_func/lead_Fn_69")
   @Test
   public void test_lead_func_lead_Fn_69()
@@ -4473,7 +4468,7 @@ public void test_lead_func_lead_Fn_69()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.MISSING_DESC)
+  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("nestedAggs/multiWin_7")
   @Test
   public void test_nestedAggs_multiWin_7()
@@ -4993,7 +4988,7 @@ public void test_aggregates_winFnQry_7()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_COUNT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_10")
   @Test
   public void test_aggregates_testW_Nulls_10()
@@ -5001,7 +4996,7 @@ public void test_aggregates_testW_Nulls_10()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_11")
   @Test
   public void test_aggregates_testW_Nulls_11()
@@ -5153,7 +5148,7 @@ public void test_aggregates_testW_Nulls_29()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_2")
   @Test
   public void test_aggregates_testW_Nulls_2()
@@ -5241,7 +5236,7 @@ public void test_aggregates_testW_Nulls_39()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_COUNT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_3")
   @Test
   public void test_aggregates_testW_Nulls_3()
@@ -5249,7 +5244,7 @@ public void test_aggregates_testW_Nulls_3()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_4")
   @Test
   public void test_aggregates_testW_Nulls_4()
@@ -5257,7 +5252,7 @@ public void test_aggregates_testW_Nulls_4()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.COLUMN_NOT_FOUND)
   @DrillTest("aggregates/testW_Nulls_5")
   @Test
   public void test_aggregates_testW_Nulls_5()
@@ -5265,7 +5260,7 @@ public void test_aggregates_testW_Nulls_5()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.COLUMN_NOT_FOUND)
   @DrillTest("aggregates/testW_Nulls_6")
   @Test
   public void test_aggregates_testW_Nulls_6()
@@ -5273,7 +5268,7 @@ public void test_aggregates_testW_Nulls_6()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_7")
   @Test
   public void test_aggregates_testW_Nulls_7()
@@ -5281,7 +5276,6 @@ public void test_aggregates_testW_Nulls_7()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("aggregates/testW_Nulls_8")
   @Test
   public void test_aggregates_testW_Nulls_8()
@@ -5289,7 +5283,7 @@ public void test_aggregates_testW_Nulls_8()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/testW_Nulls_9")
   @Test
   public void test_aggregates_testW_Nulls_9()
@@ -5297,7 +5291,7 @@ public void test_aggregates_testW_Nulls_9()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_61")
   @Test
   public void test_aggregates_winFnQry_61()
@@ -5305,7 +5299,7 @@ public void test_aggregates_winFnQry_61()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_62")
   @Test
   public void test_aggregates_winFnQry_62()
@@ -5313,7 +5307,7 @@ public void test_aggregates_winFnQry_62()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_64")
   @Test
   public void test_aggregates_winFnQry_64()
@@ -5321,7 +5315,7 @@ public void test_aggregates_winFnQry_64()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_65")
   @Test
   public void test_aggregates_winFnQry_65()
@@ -5409,7 +5403,7 @@ public void test_aggregates_winFnQry_75()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_76")
   @Test
   public void test_aggregates_winFnQry_76()
@@ -5417,7 +5411,7 @@ public void test_aggregates_winFnQry_76()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_77")
   @Test
   public void test_aggregates_winFnQry_77()
@@ -5425,7 +5419,7 @@ public void test_aggregates_winFnQry_77()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_78")
   @Test
   public void test_aggregates_winFnQry_78()
@@ -5433,7 +5427,7 @@ public void test_aggregates_winFnQry_78()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_COUNT_MISMATCH)
   @DrillTest("aggregates/winFnQry_79")
   @Test
   public void test_aggregates_winFnQry_79()
@@ -5441,7 +5435,7 @@ public void test_aggregates_winFnQry_79()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_COUNT_MISMATCH)
   @DrillTest("aggregates/winFnQry_80")
   @Test
   public void test_aggregates_winFnQry_80()
@@ -5449,7 +5443,7 @@ public void test_aggregates_winFnQry_80()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_COUNT_MISMATCH)
   @DrillTest("aggregates/winFnQry_81")
   @Test
   public void test_aggregates_winFnQry_81()
@@ -5457,7 +5451,7 @@ public void test_aggregates_winFnQry_81()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/winFnQry_82")
   @Test
   public void test_aggregates_winFnQry_82()
@@ -5465,7 +5459,6 @@ public void test_aggregates_winFnQry_82()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_10")
   @Test
   public void test_lag_func_lag_Fn_10()
@@ -5473,7 +5466,6 @@ public void test_lag_func_lag_Fn_10()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_11")
   @Test
   public void test_lag_func_lag_Fn_11()
@@ -5481,7 +5473,6 @@ public void test_lag_func_lag_Fn_11()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_12")
   @Test
   public void test_lag_func_lag_Fn_12()
@@ -5489,7 +5480,6 @@ public void test_lag_func_lag_Fn_12()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_13")
   @Test
   public void test_lag_func_lag_Fn_13()
@@ -5497,7 +5487,6 @@ public void test_lag_func_lag_Fn_13()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_14")
   @Test
   public void test_lag_func_lag_Fn_14()
@@ -5505,7 +5494,7 @@ public void test_lag_func_lag_Fn_14()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lag_func/lag_Fn_15")
   @Test
   public void test_lag_func_lag_Fn_15()
@@ -5513,7 +5502,6 @@ public void test_lag_func_lag_Fn_15()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_16")
   @Test
   public void test_lag_func_lag_Fn_16()
@@ -5521,7 +5509,6 @@ public void test_lag_func_lag_Fn_16()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_17")
   @Test
   public void test_lag_func_lag_Fn_17()
@@ -5529,7 +5516,6 @@ public void test_lag_func_lag_Fn_17()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_18")
   @Test
   public void test_lag_func_lag_Fn_18()
@@ -5537,7 +5523,7 @@ public void test_lag_func_lag_Fn_18()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_19")
   @Test
   public void test_lag_func_lag_Fn_19()
@@ -5545,7 +5531,7 @@ public void test_lag_func_lag_Fn_19()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_20")
   @Test
   public void test_lag_func_lag_Fn_20()
@@ -5553,7 +5539,7 @@ public void test_lag_func_lag_Fn_20()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_21")
   @Test
   public void test_lag_func_lag_Fn_21()
@@ -5561,7 +5547,7 @@ public void test_lag_func_lag_Fn_21()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_22")
   @Test
   public void test_lag_func_lag_Fn_22()
@@ -5577,7 +5563,7 @@ public void test_lag_func_lag_Fn_23()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_24")
   @Test
   public void test_lag_func_lag_Fn_24()
@@ -5585,7 +5571,7 @@ public void test_lag_func_lag_Fn_24()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_25")
   @Test
   public void test_lag_func_lag_Fn_25()
@@ -5593,7 +5579,7 @@ public void test_lag_func_lag_Fn_25()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_26")
   @Test
   public void test_lag_func_lag_Fn_26()
@@ -5601,7 +5587,7 @@ public void test_lag_func_lag_Fn_26()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_54")
   @Test
   public void test_lag_func_lag_Fn_54()
@@ -5609,7 +5595,6 @@ public void test_lag_func_lag_Fn_54()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_64")
   @Test
   public void test_lag_func_lag_Fn_64()
@@ -5617,7 +5602,6 @@ public void test_lag_func_lag_Fn_64()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_65")
   @Test
   public void test_lag_func_lag_Fn_65()
@@ -5625,7 +5609,6 @@ public void test_lag_func_lag_Fn_65()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_66")
   @Test
   public void test_lag_func_lag_Fn_66()
@@ -5633,7 +5616,6 @@ public void test_lag_func_lag_Fn_66()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_67")
   @Test
   public void test_lag_func_lag_Fn_67()
@@ -5641,7 +5623,7 @@ public void test_lag_func_lag_Fn_67()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_68")
   @Test
   public void test_lag_func_lag_Fn_68()
@@ -5649,7 +5631,6 @@ public void test_lag_func_lag_Fn_68()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lag_func/lag_Fn_71")
   @Test
   public void test_lag_func_lag_Fn_71()
@@ -5657,7 +5638,7 @@ public void test_lag_func_lag_Fn_71()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lag_func/lag_Fn_72")
   @Test
   public void test_lag_func_lag_Fn_72()
@@ -5665,7 +5646,6 @@ public void test_lag_func_lag_Fn_72()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_10")
   @Test
   public void test_lead_func_lead_Fn_10()
@@ -5673,7 +5653,6 @@ public void test_lead_func_lead_Fn_10()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_11")
   @Test
   public void test_lead_func_lead_Fn_11()
@@ -5681,7 +5660,6 @@ public void test_lead_func_lead_Fn_11()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_12")
   @Test
   public void test_lead_func_lead_Fn_12()
@@ -5689,7 +5667,6 @@ public void test_lead_func_lead_Fn_12()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_13")
   @Test
   public void test_lead_func_lead_Fn_13()
@@ -5697,7 +5674,6 @@ public void test_lead_func_lead_Fn_13()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_14")
   @Test
   public void test_lead_func_lead_Fn_14()
@@ -5705,7 +5681,7 @@ public void test_lead_func_lead_Fn_14()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lead_func/lead_Fn_15")
   @Test
   public void test_lead_func_lead_Fn_15()
@@ -5713,7 +5689,6 @@ public void test_lead_func_lead_Fn_15()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_16")
   @Test
   public void test_lead_func_lead_Fn_16()
@@ -5721,7 +5696,6 @@ public void test_lead_func_lead_Fn_16()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_17")
   @Test
   public void test_lead_func_lead_Fn_17()
@@ -5729,7 +5703,6 @@ public void test_lead_func_lead_Fn_17()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_18")
   @Test
   public void test_lead_func_lead_Fn_18()
@@ -5737,7 +5710,7 @@ public void test_lead_func_lead_Fn_18()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lead_func/lead_Fn_19")
   @Test
   public void test_lead_func_lead_Fn_19()
@@ -5753,7 +5726,7 @@ public void test_lead_func_lead_Fn_20()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lead_func/lead_Fn_21")
   @Test
   public void test_lead_func_lead_Fn_21()
@@ -5761,7 +5734,7 @@ public void test_lead_func_lead_Fn_21()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lead_func/lead_Fn_22")
   @Test
   public void test_lead_func_lead_Fn_22()
@@ -5793,7 +5766,6 @@ public void test_lead_func_lead_Fn_25()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_64")
   @Test
   public void test_lead_func_lead_Fn_64()
@@ -5801,7 +5773,6 @@ public void test_lead_func_lead_Fn_64()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_65")
   @Test
   public void test_lead_func_lead_Fn_65()
@@ -5809,7 +5780,6 @@ public void test_lead_func_lead_Fn_65()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_66")
   @Test
   public void test_lead_func_lead_Fn_66()
@@ -5817,7 +5787,6 @@ public void test_lead_func_lead_Fn_66()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_67")
   @Test
   public void test_lead_func_lead_Fn_67()
@@ -5825,7 +5794,7 @@ public void test_lead_func_lead_Fn_67()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lead_func/lead_Fn_68")
   @Test
   public void test_lead_func_lead_Fn_68()
@@ -5833,7 +5802,6 @@ public void test_lead_func_lead_Fn_68()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
   @DrillTest("lead_func/lead_Fn_71")
   @Test
   public void test_lead_func_lead_Fn_71()
@@ -5841,7 +5809,7 @@ public void test_lead_func_lead_Fn_71()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.NULLS_FIRST_LAST)
+  @NotYetSupported(Modes.UNSUPPORTED_NULL_ORDERING)
   @DrillTest("lead_func/lead_Fn_72")
   @Test
   public void test_lead_func_lead_Fn_72()
@@ -6463,7 +6431,6 @@ public void test_aggregates_winFnQry_8()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/wo_OrdrBy_17")
   @Test
   public void test_aggregates_wo_OrdrBy_17()
@@ -6471,7 +6438,6 @@ public void test_aggregates_wo_OrdrBy_17()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/wo_OrdrBy_18")
   @Test
   public void test_aggregates_wo_OrdrBy_18()
@@ -6479,7 +6445,6 @@ public void test_aggregates_wo_OrdrBy_18()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/wo_OrdrBy_19")
   @Test
   public void test_aggregates_wo_OrdrBy_19()
@@ -6487,7 +6452,6 @@ public void test_aggregates_wo_OrdrBy_19()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/wo_OrdrBy_20")
   @Test
   public void test_aggregates_wo_OrdrBy_20()
@@ -6495,7 +6459,6 @@ public void test_aggregates_wo_OrdrBy_20()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("aggregates/wo_OrdrBy_21")
   @Test
   public void test_aggregates_wo_OrdrBy_21()
@@ -6679,7 +6642,6 @@ public void test_aggregates_woPrtnBy_9()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("first_val/firstValFn_17")
   @Test
   public void test_first_val_firstValFn_17()
@@ -7597,7 +7559,6 @@ public void test_lead_func_lead_Fn_51()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lead_func/lead_Fn_54")
   @Test
   public void test_lead_func_lead_Fn_54()
@@ -7613,7 +7574,6 @@ public void test_lead_func_lead_Fn_60()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lead_func/lead_Fn_63")
   @Test
   public void test_lead_func_lead_Fn_63()
@@ -7637,7 +7597,6 @@ public void test_lead_func_lead_Fn_77()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lead_func/lead_Fn_90")
   @Test
   public void test_lead_func_lead_Fn_90()
@@ -7653,7 +7612,6 @@ public void test_lead_func_lead_Fn_96()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("lead_func/lead_Fn_9")
   @Test
   public void test_lead_func_lead_Fn_9()
@@ -7669,7 +7627,6 @@ public void test_nestedAggs_basic_3()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("nestedAggs/basic_5")
   @Test
   public void test_nestedAggs_basic_5()
@@ -7756,7 +7713,6 @@ public void test_nestedAggs_woutPrtnBy_5()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.RESULT_MISMATCH)
   @DrillTest("ntile_func/ntileFn_15")
   @Test
   public void test_ntile_func_ntileFn_15()
@@ -7932,7 +7888,6 @@ public void test_lag_func_lag_Fn_60()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.T_ALLTYPES_ISSUES)
   @DrillTest("lag_func/lag_Fn_77")
   @Test
   public void test_lag_func_lag_Fn_77()
@@ -7940,7 +7895,6 @@ public void test_lag_func_lag_Fn_77()
     windowQueryTest();
   }
 
-  @NotYetSupported(Modes.T_ALLTYPES_ISSUES)
   @DrillTest("lag_func/lag_Fn_95")
   @Test
   public void test_lag_func_lag_Fn_95()
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/NotYetSupported.java b/sql/src/test/java/org/apache/druid/sql/calcite/NotYetSupported.java
index 32364f6a8b19..933359e96bf6 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/NotYetSupported.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/NotYetSupported.java
@@ -88,7 +88,8 @@ enum Modes
     INCORRECT_SYNTAX(DruidException.class, "Incorrect syntax near the keyword"),
     // at least c7 is represented oddly in the parquet file
     T_ALLTYPES_ISSUES(AssertionError.class, "(t_alltype|allTypsUniq|fewRowsAllData).parquet.*Verifier.verify"),
-    RESULT_MISMATCH(AssertionError.class, "assertResultsEquals");
+    RESULT_MISMATCH(AssertionError.class, "assertResultsEquals"),
+    UNSUPPORTED_NULL_ORDERING(DruidException.class, "(A|DE)SCENDING ordering with NULLS (LAST|FIRST)");
 
     public Class<? extends Throwable> throwableClass;
     public String regex;
diff --git a/sql/src/test/resources/calcite/tests/window/orderByDescNulls.sqlTest b/sql/src/test/resources/calcite/tests/window/orderByDescNulls.sqlTest
new file mode 100644
index 000000000000..320b448c7488
--- /dev/null
+++ b/sql/src/test/resources/calcite/tests/window/orderByDescNulls.sqlTest
@@ -0,0 +1,45 @@
+type: "operatorValidation"
+
+sql: |
+    SELECT
+      cityName,
+      __time,
+      ROW_NUMBER() OVER (ORDER BY cityName desc nulls last, __time ) windowedDelta,
+      ROW_NUMBER() OVER (ORDER BY cityName nulls first, __time ) windowedDelta
+    FROM wikipedia
+    where page < '0' and channel like '#en%'
+
+expectedOperators:
+  - type: "naiveSort"
+    columns:
+      - column: "cityName"
+        direction: "DESC"
+      - column: "__time"
+        direction: "ASC"
+  - type: "naivePartition"
+    partitionColumns: [ ]
+  - type: "window"
+    processor:
+      type: "rowNumber"
+      outputColumn: "w0"
+  - type: "naiveSort"
+    columns:
+      - column: "cityName"
+        direction: "ASC"
+      - column: "__time"
+        direction: "ASC"
+  - type: "naivePartition"
+    partitionColumns: [ ]
+  - type: "window"
+    processor:
+      type: "rowNumber"
+      outputColumn: "w1"
+expectedResults:
+  - [null,1442019358364,3,1]
+  - [null,1442021099146,4,2]
+  - [null,1442033539153,5,3]
+  - [null,1442095704125,6,4]
+  - [null,1442096110867,7,5]
+  - [null,1442100368226,8,6]
+  - ["Crescent City",1442035449448,2,7]
+  - ["Vinnytsya",1442100940306,1,8]