diff --git a/hibernate-core/src/main/java/org/hibernate/dialect/SqlAstTranslatorWithMerge.java b/hibernate-core/src/main/java/org/hibernate/dialect/SqlAstTranslatorWithMerge.java
index be143614a526..5d646d225fb1 100644
--- a/hibernate-core/src/main/java/org/hibernate/dialect/SqlAstTranslatorWithMerge.java
+++ b/hibernate-core/src/main/java/org/hibernate/dialect/SqlAstTranslatorWithMerge.java
@@ -50,6 +50,11 @@ public MergeOperation createMergeOperation(OptionalTableUpdate optionalTableUpda
 		);
 	}
 
+	@Override
+	public void visitOptionalTableUpdate(OptionalTableUpdate tableUpdate) {
+		renderMergeStatement(tableUpdate);
+	}
+
 	/**
 	 * Renders the OptionalTableUpdate as a MERGE query.
 	 *
@@ -207,8 +212,9 @@ protected void renderMergeInsert(OptionalTableUpdate optionalTableUpdate) {
 
 	protected void renderMergeDelete(OptionalTableUpdate optionalTableUpdate) {
 		final List<ColumnValueBinding> valueBindings = optionalTableUpdate.getValueBindings();
+		final List<ColumnValueBinding> optimisticLockBindings = optionalTableUpdate.getOptimisticLockBindings();
 
-		appendSql( " when matched " );
+		renderWhenMatched( optimisticLockBindings );
 		for ( int i = 0; i < valueBindings.size(); i++ ) {
 			final ColumnValueBinding binding = valueBindings.get( i );
 			appendSql( " and " );
@@ -220,8 +226,10 @@ protected void renderMergeDelete(OptionalTableUpdate optionalTableUpdate) {
 
 	protected void renderMergeUpdate(OptionalTableUpdate optionalTableUpdate) {
 		final List<ColumnValueBinding> valueBindings = optionalTableUpdate.getValueBindings();
+		final List<ColumnValueBinding> optimisticLockBindings = optionalTableUpdate.getOptimisticLockBindings();
 
-		appendSql( " when matched then update set " );
+		renderWhenMatched( optimisticLockBindings );
+		appendSql( " then update set " );
 		for ( int i = 0; i < valueBindings.size(); i++ ) {
 			final ColumnValueBinding binding = valueBindings.get( i );
 			if ( i > 0 ) {
@@ -232,4 +240,15 @@ protected void renderMergeUpdate(OptionalTableUpdate optionalTableUpdate) {
 			binding.getColumnReference().appendColumnForWrite( this, "s" );
 		}
 	}
+
+	private void renderWhenMatched(List<ColumnValueBinding> optimisticLockBindings) {
+		appendSql( " when matched" );
+		for (int i = 0; i < optimisticLockBindings.size(); i++) {
+			final ColumnValueBinding binding = optimisticLockBindings.get( i );
+			appendSql(" and ");
+			binding.getColumnReference().appendColumnForWrite( this, "t" );
+			appendSql("<=");
+			binding.getValueExpression().accept( this );
+		}
+	}
 }
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/stateless/UpsertVersionedTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/stateless/UpsertVersionedTest.java
index 1ae36bb72a2c..e6363d4f2baf 100644
--- a/hibernate-core/src/test/java/org/hibernate/orm/test/stateless/UpsertVersionedTest.java
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/stateless/UpsertVersionedTest.java
@@ -15,7 +15,7 @@
 public class UpsertVersionedTest {
     @Test void test(SessionFactoryScope scope) {
         scope.inStatelessTransaction(s-> {
-            s.upsert(new Record(123L,1L,"hello earth"));
+            s.upsert(new Record(123L,0L,"hello earth"));
             s.upsert(new Record(456L,2L,"hello mars"));
         });
         scope.inStatelessTransaction(s-> {