diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java b/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
index 95a33792189..691e9518659 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
@@ -1078,6 +1078,12 @@ public class DruidQuery
           virtualColumnRegistry,
           plannerContext.getJoinableFactoryWrapper()
       );
+
+      if (!getVirtualColumns(true).isEmpty()) {
+        // timeBoundary query does not support virtual columns.
+        return null;
+      }
+
       final DataSource newDataSource = dataSourceFiltrationPair.lhs;
       final Filtration filtration = dataSourceFiltrationPair.rhs;
       String bound = minTime ? TimeBoundaryQuery.MIN_TIME : TimeBoundaryQuery.MAX_TIME;
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteTimeBoundaryQueryTest.java b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteTimeBoundaryQueryTest.java
index ff0555cb358..54ff1a2c00e 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteTimeBoundaryQueryTest.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteTimeBoundaryQueryTest.java
@@ -30,6 +30,7 @@ import org.apache.druid.query.aggregation.LongMaxAggregatorFactory;
 import org.apache.druid.query.aggregation.LongMinAggregatorFactory;
 import org.apache.druid.query.spec.MultipleIntervalSegmentSpec;
 import org.apache.druid.query.timeboundary.TimeBoundaryQuery;
+import org.apache.druid.segment.column.ColumnType;
 import org.apache.druid.segment.join.JoinType;
 import org.apache.druid.sql.calcite.filtration.Filtration;
 import org.apache.druid.sql.calcite.util.CalciteTests;
@@ -83,7 +84,7 @@ public class CalciteTimeBoundaryQueryTest extends BaseCalciteQueryTest
   }
 
   @Test
-  public void testMinTimeQueryWithFilters()
+  public void testMinTimeQueryWithTimeFilters()
   {
     HashMap<String, Object> queryContext = new HashMap<>(QUERY_CONTEXT_DEFAULT);
     queryContext.put(QueryContexts.TIME_BOUNDARY_PLANNING_KEY, true);
@@ -108,6 +109,66 @@ public class CalciteTimeBoundaryQueryTest extends BaseCalciteQueryTest
     );
   }
 
+  @Test
+  public void testMinTimeQueryWithTimeAndColumnFilters()
+  {
+    HashMap<String, Object> queryContext = new HashMap<>(QUERY_CONTEXT_DEFAULT);
+    queryContext.put(QueryContexts.TIME_BOUNDARY_PLANNING_KEY, true);
+    HashMap<String, Object> expectedContext = new HashMap<>(QUERY_CONTEXT_DEFAULT);
+    expectedContext.put(TimeBoundaryQuery.MIN_TIME_ARRAY_OUTPUT_NAME, "a0");
+    testQuery(
+        "SELECT MIN(__time) AS minTime FROM foo\n"
+        + "where __time >= '2001-01-01' and __time < '2003-01-01'\n"
+        + "and dim2 = 'abc'",
+        queryContext,
+        ImmutableList.of(
+            Druids.newTimeBoundaryQueryBuilder()
+                  .dataSource("foo")
+                  .intervals(
+                      new MultipleIntervalSegmentSpec(
+                          ImmutableList.of(Intervals.of("2001-01-01T00:00:00.000Z/2003-01-01T00:00:00.000Z"))
+                      )
+                  )
+                  .bound(TimeBoundaryQuery.MIN_TIME)
+                  .filters(equality("dim2", "abc", ColumnType.STRING))
+                  .context(expectedContext)
+                  .build()
+        ),
+        ImmutableList.of(new Object[]{DateTimes.of("2001-01-02").getMillis()})
+    );
+  }
+
+  @Test
+  public void testMinTimeQueryWithTimeAndExpressionFilters()
+  {
+    // Cannot vectorize due to UPPER expression.
+    cannotVectorize();
+
+    HashMap<String, Object> queryContext = new HashMap<>(QUERY_CONTEXT_DEFAULT);
+    queryContext.put(QueryContexts.TIME_BOUNDARY_PLANNING_KEY, true);
+    testQuery(
+        "SELECT MIN(__time) AS minTime FROM foo\n"
+        + "where __time >= '2001-01-01' and __time < '2003-01-01'\n"
+        + "and upper(dim2) = 'ABC'",
+        queryContext,
+        ImmutableList.of(
+            Druids.newTimeseriesQueryBuilder()
+                  .dataSource("foo")
+                  .intervals(
+                      new MultipleIntervalSegmentSpec(
+                          ImmutableList.of(Intervals.of("2001-01-01T00:00:00.000Z/2003-01-01T00:00:00.000Z"))
+                      )
+                  )
+                  .virtualColumns(expressionVirtualColumn("v0", "upper(\"dim2\")", ColumnType.STRING))
+                  .filters(equality("v0", "ABC", ColumnType.STRING))
+                  .aggregators(new LongMinAggregatorFactory("a0", "__time"))
+                  .context(queryContext)
+                  .build()
+        ),
+        ImmutableList.of(new Object[]{DateTimes.of("2001-01-02").getMillis()})
+    );
+  }
+
   // Currently, if both min(__time) and max(__time) are present, we don't convert it
   // to a timeBoundary query. (ref : https://github.com/apache/druid/issues/12479)
   @Test