diff --git a/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Leaf.java b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Leaf.java
new file mode 100644
index 0000000000..e0fb72e258
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Leaf.java
@@ -0,0 +1,61 @@
+/*
+ * 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.bytecode.enhancement.merge;
+
+import javax.persistence.Access;
+import javax.persistence.AccessType;
+import javax.persistence.Column;
+import javax.persistence.Entity;
+import javax.persistence.GeneratedValue;
+import javax.persistence.GenerationType;
+import javax.persistence.Id;
+import javax.persistence.JoinColumn;
+import javax.persistence.ManyToOne;
+import javax.persistence.SequenceGenerator;
+
+/**
+ * @author Chris Cranford
+ */
+@Entity
+@Access(AccessType.FIELD)
+public class Leaf {
+	@Id
+	@GeneratedValue(strategy = GenerationType.SEQUENCE, generator="LEAF_SEQ")
+	@SequenceGenerator(name = "LEAF_SEQ", sequenceName = "LEAF_SEQ")
+	private Long id;
+
+	@ManyToOne(optional = false)
+	@JoinColumn(name = "ROOD_ID", nullable = false)
+	private Root root;
+
+	@Column
+	private String name;
+
+	public Long getId() {
+		return id;
+	}
+
+	public void setId(Long id) {
+		this.id = id;
+	}
+
+	public Root getRoot() {
+		return root;
+	}
+
+	public void setRoot(Root root) {
+		this.root = root;
+	}
+
+	public String getName() {
+		return name;
+	}
+
+	public void setName(String name) {
+		this.name = name;
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/MergeEnhancedDetachedOrphanRemovalTest.java b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/MergeEnhancedDetachedOrphanRemovalTest.java
new file mode 100644
index 0000000000..86836ee81a
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/MergeEnhancedDetachedOrphanRemovalTest.java
@@ -0,0 +1,43 @@
+/*
+ * 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.bytecode.enhancement.merge;
+
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.bytecode.enhancement.BytecodeEnhancerRunner;
+import org.hibernate.testing.junit4.BaseCoreFunctionalTestCase;
+
+import static org.hibernate.testing.transaction.TransactionUtil.doInHibernate;
+
+/**
+ * @author Chris Cranford
+ */
+@TestForIssue(jiraKey = "HHH-12592")
+@RunWith(BytecodeEnhancerRunner.class)
+public class MergeEnhancedDetachedOrphanRemovalTest extends BaseCoreFunctionalTestCase {
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class<?>[] { Leaf.class, Root.class };
+	}
+
+	@Test
+	public void testMergeDetachedOrphanRemoval() {
+		final Root entity = doInHibernate( this::sessionFactory, session -> {
+			Root root = new Root();
+			root.setName( "new" );
+			session.save( root );
+			return root;
+		} );
+
+		doInHibernate( this::sessionFactory, session -> {
+			entity.setName( "updated" );
+			session.merge( entity );
+		} );
+	}
+}
diff --git a/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Root.java b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Root.java
new file mode 100644
index 0000000000..6b33486db9
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/test/bytecode/enhancement/merge/Root.java
@@ -0,0 +1,61 @@
+/*
+ * 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.bytecode.enhancement.merge;
+
+import java.util.HashSet;
+import java.util.Set;
+
+import javax.persistence.Access;
+import javax.persistence.AccessType;
+import javax.persistence.CascadeType;
+import javax.persistence.Column;
+import javax.persistence.Entity;
+import javax.persistence.GeneratedValue;
+import javax.persistence.GenerationType;
+import javax.persistence.Id;
+import javax.persistence.OneToMany;
+import javax.persistence.SequenceGenerator;
+
+/**
+ * @author Chris Cranford
+ */
+@Entity
+@Access(AccessType.PROPERTY)
+public class Root {
+	private Long id;
+	private String name;
+	private Set<Leaf> leaves = new HashSet<>();
+
+	@Id
+	@GeneratedValue(strategy = GenerationType.SEQUENCE, generator = "ROOT_SEQ")
+	@SequenceGenerator(name = "ROOT_SEQ", sequenceName = "ROOT_SEQ")
+	public Long getId() {
+		return id;
+	}
+
+	public void setId(Long id) {
+		this.id = id;
+	}
+
+	@Column(name = "NAME", length = 50)
+	public String getName() {
+		return name;
+	}
+
+	public void setName(String name) {
+		this.name = name;
+	}
+
+	@OneToMany(cascade = CascadeType.ALL, orphanRemoval = true)
+	public Set<Leaf> getLeaves() {
+		return leaves;
+	}
+
+	public void setLeaves(Set<Leaf> leaves) {
+		this.leaves = leaves;
+	}
+}