diff --git a/hibernate-core/src/test/java/org/hibernate/test/annotations/list/ListMappingTest.java b/hibernate-core/src/test/java/org/hibernate/test/annotations/list/ListMappingTest.java
new file mode 100644
index 0000000000..c706909908
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/test/annotations/list/ListMappingTest.java
@@ -0,0 +1,187 @@
+/*
+ * Hibernate, Relational Persistence for Idiomatic Java
+ *
+ * License: GNU Lesser General Public License (LGPL), version 2.1 or later.
+ * See the lgpl.txt file in the root directory or <http://www.gnu.org/licenses/lgpl-2.1.html>.
+ */
+package org.hibernate.test.annotations.list;
+
+import java.util.ArrayList;
+import java.util.Collections;
+import java.util.List;
+import javax.persistence.Entity;
+import javax.persistence.Id;
+import javax.persistence.JoinColumn;
+import javax.persistence.ManyToOne;
+import javax.persistence.OneToMany;
+import javax.persistence.OrderColumn;
+import javax.persistence.Table;
+
+import org.hibernate.boot.Metadata;
+import org.hibernate.boot.MetadataSources;
+import org.hibernate.boot.registry.StandardServiceRegistry;
+import org.hibernate.boot.registry.StandardServiceRegistryBuilder;
+import org.hibernate.mapping.Collection;
+import org.hibernate.mapping.Column;
+import org.hibernate.tool.schema.internal.TargetStdoutImpl;
+import org.hibernate.tool.schema.spi.SchemaManagementTool;
+import org.hibernate.tool.schema.spi.Target;
+
+import org.hibernate.testing.junit4.BaseUnitTestCase;
+import org.junit.After;
+import org.junit.Before;
+import org.junit.Test;
+
+import static org.hamcrest.CoreMatchers.equalTo;
+import static org.hamcrest.CoreMatchers.instanceOf;
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.junit.Assert.assertTrue;
+
+/**
+ * Originally developed to help diagnose HHH-10099 which reports a problem with @OrderColumn
+ * not being bound
+ *
+ * @author Steve Ebersole
+ */
+public class ListMappingTest extends BaseUnitTestCase {
+	private StandardServiceRegistry ssr;
+
+	@Before
+	public void before() {
+		ssr = new StandardServiceRegistryBuilder()
+				.build();
+	}
+
+	@After
+	public void after() {
+		if ( ssr != null ) {
+			StandardServiceRegistryBuilder.destroy( ssr );
+		}
+	}
+
+	@Test
+	public void testOrderColumnInNormalBiDirectonalModel() {
+		Metadata metadata = new MetadataSources( ssr )
+				.addAnnotatedClass( Order.class )
+				.addAnnotatedClass( LineItem.class )
+				.buildMetadata();
+
+		Collection lineItemsBinding = metadata.getCollectionBindings().iterator().next();
+
+		// make sure it was interpreted as a List (aka, as having an OrderColumn at all)
+		assertThat( lineItemsBinding, instanceOf( org.hibernate.mapping.List.class ) );
+		org.hibernate.mapping.List asList = (org.hibernate.mapping.List) lineItemsBinding;
+
+		// assert the OrderColumn details
+		final Column positionColumn = (Column) asList.getIndex().getColumnIterator().next();
+		assertThat( positionColumn.getName(), equalTo( "position" ) );
+
+		// make sure the OrderColumn is part of the collection table
+		assertTrue( asList.getCollectionTable().containsColumn( positionColumn ) );
+
+		class TargetImpl extends TargetStdoutImpl {
+			boolean found = false;
+			@Override
+			public void accept(String action) {
+				super.accept( action );
+				if ( action.startsWith( "create table t_line_item" ) ) {
+					if ( action.contains( "position" ) ) {
+						found = true;
+					}
+				}
+			}
+		}
+
+		TargetImpl target = new TargetImpl();
+
+		ssr.getService( SchemaManagementTool.class ).getSchemaCreator( Collections.emptyMap() ).doCreation(
+				metadata,
+				true,
+				Collections.<Target>singletonList( target )
+		);
+
+		assertTrue( target.found );
+	}
+
+	// ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+	// Bi-directional model
+
+	@Entity( name = "Order" )
+	@Table( name = "t_order" )
+	public static class Order {
+		private Integer id;
+		private List<LineItem> lineItems = new ArrayList<LineItem>();
+
+		@Id
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		@OneToMany( mappedBy = "order" )
+		@OrderColumn( name = "position" )
+		public List<LineItem> getLineItems() {
+			return lineItems;
+		}
+
+		public void setLineItems(List<LineItem> lineItems) {
+			this.lineItems = lineItems;
+		}
+	}
+
+	@Entity( name = "LineItem" )
+	@Table( name = "t_line_item" )
+	public static class LineItem {
+		private Integer id;
+		private Order order;
+		private String product;
+		private int quantity;
+		private String discountCode;
+
+		@Id
+		public Integer getId() {
+			return id;
+		}
+
+		public void setId(Integer id) {
+			this.id = id;
+		}
+
+		@ManyToOne( optional = false )
+		@JoinColumn( name = "order_id" )
+		public Order getOrder() {
+			return order;
+		}
+
+		public void setOrder(Order order) {
+			this.order = order;
+		}
+
+		public String getProduct() {
+			return product;
+		}
+
+		public void setProduct(String product) {
+			this.product = product;
+		}
+
+		public int getQuantity() {
+			return quantity;
+		}
+
+		public void setQuantity(int quantity) {
+			this.quantity = quantity;
+		}
+
+		public String getDiscountCode() {
+			return discountCode;
+		}
+
+		public void setDiscountCode(String discountCode) {
+			this.discountCode = discountCode;
+		}
+	}
+}