diff --git a/hibernate-core/src/main/java/org/hibernate/persister/collection/OneToManyPersister.java b/hibernate-core/src/main/java/org/hibernate/persister/collection/OneToManyPersister.java
index ed4046f38b..2da0fe4a3b 100644
--- a/hibernate-core/src/main/java/org/hibernate/persister/collection/OneToManyPersister.java
+++ b/hibernate-core/src/main/java/org/hibernate/persister/collection/OneToManyPersister.java
@@ -208,7 +208,7 @@ public class OneToManyPersister extends AbstractCollectionPersister {
 					while ( entries.hasNext() ) {
 
 						final Object entry = entries.next();
-						if ( collection.entryExists( entry, i ) ) {
+						if ( entry != null && collection.entryExists( entry, i ) ) {
 							int offset = 1;
 							PreparedStatement st = null;
 							boolean callable = isUpdateCallable();
diff --git a/hibernate-core/src/test/java/org/hibernate/test/annotations/onetomany/OrderByTest.java b/hibernate-core/src/test/java/org/hibernate/test/annotations/onetomany/OrderByTest.java
index 15aa425284..3cf9942035 100644
--- a/hibernate-core/src/test/java/org/hibernate/test/annotations/onetomany/OrderByTest.java
+++ b/hibernate-core/src/test/java/org/hibernate/test/annotations/onetomany/OrderByTest.java
@@ -364,6 +364,10 @@ public class OrderByTest extends BaseCoreFunctionalTestCase {
 		catch ( SQLException e ) {
 			fail(e.getMessage());
 		}
+		finally {
+			s.getTransaction().rollback();
+			s.close();
+		}
 	}
 	
 	@Test
diff --git a/hibernate-core/src/test/java/org/hibernate/test/collection/map/PersistentMapTest.java b/hibernate-core/src/test/java/org/hibernate/test/collection/map/PersistentMapTest.java
index 5d228b7500..28665abbbb 100644
--- a/hibernate-core/src/test/java/org/hibernate/test/collection/map/PersistentMapTest.java
+++ b/hibernate-core/src/test/java/org/hibernate/test/collection/map/PersistentMapTest.java
@@ -22,30 +22,49 @@
  * Boston, MA  02110-1301  USA
  */
 package org.hibernate.test.collection.map;
-import java.util.HashMap;
-
-import org.junit.Test;
-
-import org.hibernate.Session;
-import org.hibernate.collection.internal.PersistentMap;
-import org.hibernate.testing.junit4.BaseCoreFunctionalTestCase;
-
 import static org.junit.Assert.assertEquals;
 import static org.junit.Assert.assertFalse;
 import static org.junit.Assert.assertNotNull;
 import static org.junit.Assert.assertNull;
 import static org.junit.Assert.assertTrue;
 
+import java.io.Serializable;
+import java.util.HashMap;
+import java.util.Map;
+
+import javax.persistence.CascadeType;
+import javax.persistence.Entity;
+import javax.persistence.FetchType;
+import javax.persistence.GeneratedValue;
+import javax.persistence.Id;
+import javax.persistence.JoinColumn;
+import javax.persistence.ManyToOne;
+import javax.persistence.MapKeyColumn;
+import javax.persistence.OneToMany;
+
+import org.hibernate.Query;
+import org.hibernate.Session;
+import org.hibernate.collection.internal.PersistentMap;
+import org.hibernate.testing.TestForIssue;
+import org.hibernate.testing.junit4.BaseCoreFunctionalTestCase;
+import org.junit.Test;
+
 /**
  * Test various situations using a {@link PersistentMap}.
  *
  * @author Steve Ebersole
+ * @author Brett Meyer
  */
 public class PersistentMapTest extends BaseCoreFunctionalTestCase {
 	@Override
 	public String[] getMappings() {
 		return new String[] { "collection/map/Mappings.hbm.xml" };
 	}
+	
+	@Override
+	protected Class<?>[] getAnnotatedClasses() {
+		return new Class<?>[] { User.class, UserData.class };
+	}
 
 	@Test
 	@SuppressWarnings({ "unchecked" })
@@ -157,4 +176,57 @@ public class PersistentMapTest extends BaseCoreFunctionalTestCase {
         session.getTransaction().commit();
         session.close();
     }
+	
+	@Test
+	@TestForIssue(jiraKey = "HHH-5732")
+	public void testClearMap() {
+		Session s = openSession();
+		s.beginTransaction();
+		
+		User user = new User();
+		UserData userData = new UserData();
+		userData.user = user;
+		user.userDatas.put( "foo", userData );
+		s.persist( user );
+		
+		s.getTransaction().commit();
+		s.clear();
+		
+		s.beginTransaction();
+		
+		user = (User) s.get( User.class, 1 );
+	    user.userDatas.clear();
+	    s.update( user );
+		Query q = s.createQuery( "DELETE FROM " + UserData.class.getName() + " d WHERE d.user = :user" );
+		q.setParameter( "user", user );
+		q.executeUpdate();
+		
+		s.getTransaction().commit();
+		s.clear();
+		
+		assertEquals( ( (User) s.get( User.class, user.id ) ).userDatas.size(), 0 );
+		assertEquals( s.createQuery( "FROM " + UserData.class.getName() ).list().size(), 0 );
+		
+		s.close();
+	}
+	
+	@Entity
+	private static class User implements Serializable {
+		@Id @GeneratedValue
+		private Integer id;
+		
+		@OneToMany(fetch = FetchType.LAZY, mappedBy = "user", cascade = CascadeType.ALL)
+		@MapKeyColumn(name = "name", nullable = true)
+		private Map<String, UserData> userDatas = new HashMap<String, UserData>();
+	}
+	
+	@Entity
+	private static class UserData {
+		@Id @GeneratedValue
+		private Integer id;
+		
+		@ManyToOne
+		@JoinColumn(name = "userId")
+		private User user;
+	}
 }