diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestAnySqlAggregator.java b/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestAnySqlAggregator.java
index 58fd083dcab..ba061483639 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestAnySqlAggregator.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestAnySqlAggregator.java
@@ -202,12 +202,20 @@ public class EarliestLatestAnySqlAggregator implements SqlAggregator
         theAggFactory = aggregatorType.createAggregatorFactory(aggregatorName, fieldName, null, outputType, -1);
         break;
       case 2:
+        int maxStringBytes;
+        try {
+          maxStringBytes = RexLiteral.intValue(rexNodes.get(1));
+        }
+        catch (AssertionError ae) {
+          plannerContext.setPlanningError("The second argument '%s' to function '%s' is not a number", rexNodes.get(1), aggregateCall.getName());
+          return null;
+        }
         theAggFactory = aggregatorType.createAggregatorFactory(
             aggregatorName,
             fieldName,
             null,
             outputType,
-            RexLiteral.intValue(rexNodes.get(1))
+            maxStringBytes
         );
         break;
       default:
diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestBySqlAggregator.java b/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestBySqlAggregator.java
index f13a918e6fa..46762306a45 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestBySqlAggregator.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/aggregation/builtin/EarliestLatestBySqlAggregator.java
@@ -122,12 +122,20 @@ public class EarliestLatestBySqlAggregator implements SqlAggregator
         );
         break;
       case 3:
+        int maxStringBytes;
+        try {
+          maxStringBytes = RexLiteral.intValue(rexNodes.get(2));
+        }
+        catch (AssertionError ae) {
+          plannerContext.setPlanningError("The third argument '%s' to function '%s' is not a number", rexNodes.get(2), aggregateCall.getName());
+          return null;
+        }
         theAggFactory = aggregatorType.createAggregatorFactory(
             aggregatorName,
             fieldName,
             EarliestLatestAnySqlAggregator.getColumnName(plannerContext, virtualColumnRegistry, args.get(1), rexNodes.get(1)),
             outputType,
-            RexLiteral.intValue(rexNodes.get(2))
+            maxStringBytes
         );
         break;
       default:
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 15be7d30b23..9d6fcd0c336 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
@@ -997,6 +997,56 @@ public class CalciteQueryTest extends BaseCalciteQueryTest
     );
   }
 
+  @Test
+  public void testStringLatestGroupByWithAlwaysFalseCondition()
+  {
+    testQuery(
+        "SELECT LATEST(dim4, 10),dim2 FROM numfoo WHERE (dim1 = 'something' AND dim1 IN( 'something else') ) GROUP BY dim2",
+        ImmutableList.of(
+            Druids.newScanQueryBuilder()
+                .dataSource(InlineDataSource.fromIterable(
+                    ImmutableList.of(),
+                    RowSignature.builder()
+                        .add("EXPR$0", ColumnType.STRING)
+                        .add("dim2", ColumnType.STRING)
+                        .build()
+                ))
+                .intervals(querySegmentSpec(Filtration.eternity()))
+                .columns("EXPR$0", "dim2")
+                .context(QUERY_CONTEXT_DEFAULT)
+                .resultFormat(ResultFormat.RESULT_FORMAT_COMPACTED_LIST)
+                .legacy(false)
+                .build()
+        ),
+        ImmutableList.of()
+    );
+  }
+
+  @Test
+  public void testStringLatestByGroupByWithAlwaysFalseCondition()
+  {
+    testQuery(
+        "SELECT LATEST_BY(dim4, __time, 10),dim2 FROM numfoo WHERE (dim1 = 'something' AND dim1 IN( 'something else') ) GROUP BY dim2",
+        ImmutableList.of(
+            Druids.newScanQueryBuilder()
+                .dataSource(InlineDataSource.fromIterable(
+                    ImmutableList.of(),
+                    RowSignature.builder()
+                        .add("EXPR$0", ColumnType.STRING)
+                        .add("dim2", ColumnType.STRING)
+                        .build()
+                ))
+                .intervals(querySegmentSpec(Filtration.eternity()))
+                .columns("EXPR$0", "dim2")
+                .context(QUERY_CONTEXT_DEFAULT)
+                .resultFormat(ResultFormat.RESULT_FORMAT_COMPACTED_LIST)
+                .legacy(false)
+                .build()
+        ),
+        ImmutableList.of()
+    );
+  }
+
   // This test the off-heap (buffer) version of the EarliestAggregator (Double/Float/Long)
   @Test
   public void testPrimitiveEarliestInSubquery()