diff --git a/src/main/java/com/avaje/ebeaninternal/server/deploy/parse/AnnotationAssocManys.java b/src/main/java/com/avaje/ebeaninternal/server/deploy/parse/AnnotationAssocManys.java
index cb741dd74..94cdfbd0f 100644
--- a/src/main/java/com/avaje/ebeaninternal/server/deploy/parse/AnnotationAssocManys.java
+++ b/src/main/java/com/avaje/ebeaninternal/server/deploy/parse/AnnotationAssocManys.java
@@ -55,6 +55,10 @@ class AnnotationAssocManys extends AnnotationParser {
     OneToMany oneToMany = get(prop, OneToMany.class);
     if (oneToMany != null) {
       readToOne(oneToMany, prop);
+      if (oneToMany.orphanRemoval()) {
+        prop.setModifyListenMode(ModifyListenMode.REMOVALS);
+        prop.getCascadeInfo().setDelete(true);
+      }
       PrivateOwned privateOwned = get(prop, PrivateOwned.class);
       if (privateOwned != null) {
         prop.setModifyListenMode(ModifyListenMode.REMOVALS);
diff --git a/src/test/java/com/avaje/tests/model/basic/TSMaster.java b/src/test/java/com/avaje/tests/model/basic/TSMaster.java
index 9de0b7b0d..cf06de99c 100644
--- a/src/test/java/com/avaje/tests/model/basic/TSMaster.java
+++ b/src/test/java/com/avaje/tests/model/basic/TSMaster.java
@@ -1,7 +1,5 @@
 package com.avaje.tests.model.basic;
 
-import com.avaje.ebean.annotation.PrivateOwned;
-
 import javax.persistence.CascadeType;
 import javax.persistence.Entity;
 import javax.persistence.GeneratedValue;
@@ -29,8 +27,7 @@ public class TSMaster {
 
   boolean active;
 
-  @OneToMany(cascade = CascadeType.ALL, mappedBy = "master")
-  @PrivateOwned
+  @OneToMany(cascade = CascadeType.ALL, mappedBy = "master", orphanRemoval = true)
   List<TSDetail> details;
 
   public Integer getId() {